Security

RSS for tag

Secure the data your app manages and control access to your app using the Security framework.

Posts under Security tag

139 Posts

Post

Replies

Boosts

Views

Activity

SecItem: Fundamentals
I regularly help developers with keychain problems, both here on DevForums and for my Day Job™ in DTS. Many of these problems are caused by a fundamental misunderstanding of how the keychain works. This post is my attempt to explain that. I wrote it primarily so that Future Quinn™ can direct folks here rather than explain everything from scratch (-: If you have questions or comments about any of this, put them in a new thread and apply the Security tag so that I see it. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" SecItem: Fundamentals or How I Learned to Stop Worrying and Love the SecItem API The SecItem API seems very simple. After all, it only has four function calls, how hard can it be? In reality, things are not that easy. Various factors contribute to making this API much trickier than it might seem at first glance. This post explains the fundamental underpinnings of the keychain. For information about specific issues, see its companion post, SecItem: Pitfalls and Best Practices. Keychain Documentation Your basic starting point should be Keychain Items. If your code runs on the Mac, also read TN3137 On Mac keychain APIs and implementations. Read the doc comments in <Security/SecItem.h>. In many cases those doc comments contain critical tidbits. When you read keychain documentation [1] and doc comments, keep in mind that statements specific to iOS typically apply to iPadOS, tvOS, and watchOS as well (r. 102786959). Also, they typically apply to macOS when you target the data protection keychain. Conversely, statements specific to macOS may not apply when you target the data protection keychain. [1] Except TN3137, which is very clear about this (-: Caveat Mac Developer macOS supports two different keychain implementations: the original file-based keychain and the iOS-style data protection keychain. IMPORTANT If you’re able to use the data protection keychain, do so. It’ll make your life easier. See the Careful With that Shim, Mac Developer section of SecItem: Pitfalls and Best Practices for more about this. TN3137 On Mac keychain APIs and implementations explains this distinction. It also says: The file-based keychain is on the road to deprecation. This is talking about the implementation, not any specific API. The SecItem API can’t be deprecated because it works with both the data protection keychain and the file-based keychain. However, Apple has deprecated many APIs that are specific to the file-based keychain, for example, SecKeychainCreate. TN3137 also notes that some programs, like launchd daemons, can’t use the file-based keychain. If you’re working on such a program then you don’t have to worry about the deprecation of these file-based keychain APIs. You’re already stuck with the file-based keychain implementation, so using a deprecated file-based keychain API doesn’t make things worse. The Four Freedoms^H^H^H^H^H^H^H^H Functions The SecItem API contains just four functions: SecItemAdd(_:_:) SecItemCopyMatching(_:_:) SecItemUpdate(_:_:) SecItemDelete(_:) These directly map to standard SQL database operations: SecItemAdd(_:_:) maps to INSERT. SecItemCopyMatching(_:_:) maps to SELECT. SecItemUpdate(_:_:) maps to UPDATE. SecItemDelete(_:) maps to DELETE. You can think of each keychain item class (generic password, certificate, and so on) as a separate SQL table within the database. The rows of that table are the individual keychain items for that class and the columns are the attributes of those items. Note Except for the digital identity class, kSecClassIdentity, where the values are split across the certificate and key tables. See Digital Identities Aren’t Real in SecItem: Pitfalls and Best Practices. This is not an accident. The data protection keychain is actually implemented as an SQLite database. If you’re curious about its structure, examine it on the Mac by pointing your favourite SQLite inspection tool — for example, the sqlite3 command-line tool — at the keychain database in ~/Library/Keychains/UUU/keychain-2.db, where UUU is a UUID. WARNING Do not depend on the location and structure of this file. These have changed in the past and are likely to change again in the future. If you embed knowledge of them into a shipping product, it’s likely that your product will have binary compatibility problems at some point in the future. The only reason I’m mentioning them here is because I find it helpful to poke around in the file to get a better understanding of how the API works. For information about which attributes are supported by each keychain item class — that is, what columns are in each table — see the Note box at the top of Item Attribute Keys and Values. Alternatively, look at the Attribute Key Constants doc comment in <Security/SecItem.h>. Uniqueness A critical part of the keychain model is uniqueness. How does the keychain determine if item A is the same as item B? It turns out that this is class dependent. For each keychain item class there is a set of attributes that form the uniqueness constraint for items of that class. That is, if you try to add item A where all of its attributes are the same as item B, the add fails with errSecDuplicateItem. For more information, see the errSecDuplicateItem page. It has lists of attributes that make up this uniqueness constraint, one for each class. These uniqueness constraints are a major source of confusion, as discussed in the Queries and the Uniqueness Constraints section of SecItem: Pitfalls and Best Practices. Parameter Blocks Understanding The SecItem API is a classic ‘parameter block’ API. All of its inputs are dictionaries, and you have to know which properties to set in each dictionary to achieve your desired result. Likewise for when you read properties in output dictionaries. There are five different property groups: The item class property, kSecClass, determines the class of item you’re operating on: kSecClassGenericPassword, kSecClassCertificate, and so on. The item attribute properties, like kSecAttrAccessGroup, map directly to keychain item attributes. The search properties, like kSecMatchLimit, control how the system runs a query. The return type properties, like kSecReturnAttributes, determine what values the query returns. The value type properties, like kSecValueRef perform multiple duties, as explained below. There are other properties that perform a variety of specific functions. For example, kSecUseDataProtectionKeychain tells macOS to use the data protection keychain instead of the file-based keychain. These properties are hard to describe in general; for the details, see the documentation for each such property. Inputs Each of the four SecItem functions take dictionary input parameters of the same type, CFDictionary, but these dictionaries are not the same. Different dictionaries support different property groups: The first parameter of SecItemAdd(_:_:) is an add dictionary. It supports all property groups except the search properties. The first parameter of SecItemCopyMatching(_:_:) is a query and return dictionary. It supports all property groups. The first parameter of SecItemUpdate(_:_:) is a pure query dictionary. It supports all property groups except the return type properties. Likewise for the only parameter of SecItemDelete(_:). The second parameter of SecItemUpdate(_:_:) is an update dictionary. It supports the item attribute and value type property groups. Outputs Two of the SecItem functions, SecItemAdd(_:_:) and SecItemCopyMatching(_:_:), return values. These output parameters are of type CFTypeRef because the type of value you get back depends on the return type properties you supply in the input dictionary: If you supply a single return type property, except kSecReturnAttributes, you get back a value appropriate for that return type. If you supply multiple return type properties or kSecReturnAttributes, you get back a dictionary. This supports the item attribute and value type property groups. To get a non-attribute value from this dictionary, use the value type property that corresponds to its return type property. For example, if you set kSecReturnPersistentRef in the input dictionary, use kSecValuePersistentRef to get the persistent reference from the output dictionary. In the single item case, the type of value you get back depends on the return type property and the keychain item class: For kSecReturnData you get back the keychain item’s data. This makes most sense for password items, where the data holds the password. It also works for certificate items, where you get back the DER-encoded certificate. Using this for key items is kinda sketchy. If you want to export a key, called SecKeyCopyExternalRepresentation. Using this for digital identity items is nonsensical. For kSecReturnRef you get back an object reference. This only works for keychain item classes that have an object representation, namely certificates, keys, and digital identities. You get back a SecCertificate, a SecKey, or a SecIdentity, respectively. For kSecReturnPersistentRef you get back a data value that holds the persistent reference. Value Type Subtleties There are three properties in the value type property group: kSecValueData kSecValueRef kSecValuePersistentRef Their semantics vary based on the dictionary type. For kSecValueData: In an add dictionary, this is the value of the item to add. For example, when adding a generic password item (kSecClassGenericPassword), the value of this key is a Data value containing the password. This is not supported in a query dictionary. In an update dictionary, this is the new value for the item. For kSecValueRef: In add and query dictionaries, the system infers the class property and attribute properties from the supplied object. For example, if you supply a certificate object (SecCertificate, created using SecCertificateCreateWithData), the system will infer a kSecClass value of kSecClassCertificate and various attribute values, like kSecAttrSerialNumber, from that certificate object. This is not supported in an update dictionary. For kSecValuePersistentRef: For query dictionaries, this uniquely identifies the item to operate on. This is not supported in add and update dictionaries. Revision History 2025-05-28 Expanded the Caveat Mac Developer section to cover some subtleties associated with the deprecation of the file-based keychain. 2023-09-12 Fixed various bugs in the revision history. Added a paragraph explaining how to determine which attributes are supported by each keychain item class. 2023-02-22 Made minor editorial changes. 2023-01-28 First posted.
0
0
4.4k
May ’25
TLS for App Developers
Transport Layer Security (TLS) is the most important security protocol on the Internet today. Most notably, TLS puts the S into HTTPS, adding security to the otherwise insecure HTTP protocol. IMPORTANT TLS is the successor to the Secure Sockets Layer (SSL) protocol. SSL is no longer considered secure and it’s now rarely used in practice, although many folks still say SSL when they mean TLS. TLS is a complex protocol. Much of that complexity is hidden from app developers but there are places where it’s important to understand specific details of the protocol in order to meet your requirements. This post explains the fundamentals of TLS, concentrating on the issues that most often confuse app developers. Note The focus of this is TLS-PKI, where PKI stands for public key infrastructure. This is the standard TLS as deployed on the wider Internet. There’s another flavour of TLS, TLS-PSK, where PSK stands for pre-shared key. This has a variety of uses, but an Apple platforms we most commonly see it with local traffic, for example, to talk to a Wi-Fi based accessory. For more on how to use TLS, both TLS-PKI and TLS-PSK, in a local context, see TLS For Accessory Developers. Server Certificates For standard TLS to work the server must have a digital identity, that is, the combination of a certificate and the private key matching the public key embedded in that certificate. TLS Crypto Magic™ ensures that: The client gets a copy of the server’s certificate. The client knows that the server holds the private key matching the public key in that certificate. In a typical TLS handshake the server passes the client a list of certificates, where item 0 is the server’s certificate (the leaf certificate), item N is (optionally) the certificate of the certificate authority that ultimately issued that certificate (the root certificate), and items 1 through N-1 are any intermediate certificates required to build a cryptographic chain of trust from 0 to N. Note The cryptographic chain of trust is established by means of digital signatures. Certificate X in the chain is issued by certificate X+1. The owner of certificate X+1 uses their private key to digitally sign certificate X. The client verifies this signature using the public key embedded in certificate X+1. Eventually this chain terminates in a trusted anchor, that is, a certificate that the client trusts by default. Typically this anchor is a self-signed root certificate from a certificate authority. Note Item N is optional for reasons I’ll explain below. Also, the list of intermediate certificates may be empty (in the case where the root certificate directly issued the leaf certificate) but that’s uncommon for servers in the real world. Once the client gets the server’s certificate, it evaluates trust on that certificate to confirm that it’s talking to the right server. There are three levels of trust evaluation here: Basic X.509 trust evaluation checks that there’s a cryptographic chain of trust from the leaf through the intermediates to a trusted root certificate. The client has a set of trusted root certificates built in (these are from well-known certificate authorities, or CAs), and a site admin can add more via a configuration profile. This step also checks that none of the certificates have expired, and various other more technical criteria (like the Basic Constraints extension). Note This explains why the server does not have to include the root certificate in the list of certificates it passes to the client; the client has to have the root certificate installed if trust evaluation is to succeed. In addition, TLS trust evaluation (per RFC 2818) checks that the DNS name that you connected to matches the DNS name in the certificate. Specifically, the DNS name must be listed in the Subject Alternative Name extension. Note The Subject Alternative Name extension can also contain IP addresses, although that’s a much less well-trodden path. Also, historically it was common to accept DNS names in the Common Name element of the Subject but that is no longer the case on Apple platforms. App Transport Security (ATS) adds its own security checks. Basic X.509 and TLS trust evaluation are done for all TLS connections. ATS is only done on TLS connections made by URLSession and things layered on top URLSession (like WKWebView). In many situations you can override trust evaluation; for details, see Technote 2232 HTTPS Server Trust Evaluation). Such overrides can either tighten or loosen security. For example: You might tighten security by checking that the server certificate was issued by a specific CA. That way, if someone manages to convince a poorly-managed CA to issue them a certificate for your server, you can detect that and fail. You might loosen security by adding your own CA’s root certificate as a trusted anchor. IMPORTANT If you rely on loosened security you have to disable ATS. If you leave ATS enabled, it requires that the default server trust evaluation succeeds regardless of any customisations you do. Mutual TLS The previous section discusses server trust evaluation, which is required for all standard TLS connections. That process describes how the client decides whether to trust the server. Mutual TLS (mTLS) is the opposite of that, that is, it’s the process by which the server decides whether to trust the client. Note mTLS is commonly called client certificate authentication. I avoid that term because of the ongoing industry-wide confusion between certificates and digital identities. While it’s true that, in mTLS, the server authenticates the client certificate, to set this up on the client you need a digital identity, not a certificate. mTLS authentication is optional. The server must request a certificate from the client and the client may choose to supply one or not (although if the server requests a certificate and the client doesn’t supply one it’s likely that the server will then fail the connection). At the TLS protocol level this works much like it does with the server certificate. For the client to provide this certificate it must apply a digital identity, known as the client identity, to the connection. TLS Crypto Magic™ assures the server that, if it gets a certificate from the client, the client holds the private key associated with that certificate. Where things diverge is in trust evaluation. Trust evaluation of the client certificate is done on the server, and the server uses its own rules to decided whether to trust a specific client certificate. For example: Some servers do basic X.509 trust evaluation and then check that the chain of trust leads to one specific root certificate; that is, a client is trusted if it holds a digital identity whose certificate was issued by a specific CA. Some servers just check the certificate against a list of known trusted client certificates. When the client sends its certificate to the server it actually sends a list of certificates, much as I’ve described above for the server’s certificates. In many cases the client only needs to send item 0, that is, its leaf certificate. That’s because: The server already has the intermediate certificates required to build a chain of trust from that leaf to its root. There’s no point sending the root, as I discussed above in the context of server trust evaluation. However, there are no hard and fast rules here; the server does its client trust evaluation using its own internal logic, and it’s possible that this logic might require the client to present intermediates, or indeed present the root certificate even though it’s typically redundant. If you have problems with this, you’ll have to ask the folks running the server to explain its requirements. Note If you need to send additional certificates to the server, pass them to the certificates parameter of the method you use to create your URLCredential (typically init(identity:certificates:persistence:)). One thing that bears repeating is that trust evaluation of the client certificate is done on the server, not the client. The client doesn’t care whether the client certificate is trusted or not. Rather, it simply passes that certificate the server and it’s up to the server to make that decision. When a server requests a certificate from the client, it may supply a list of acceptable certificate authorities [1]. Safari uses this to filter the list of client identities it presents to the user. If you are building an HTTPS server and find that Safari doesn’t show the expected client identity, make sure you have this configured correctly. If you’re building an iOS app and want to implement a filter like Safari’s, get this list using: The distinguishedNames property, if you’re using URLSession The sec_protocol_metadata_access_distinguished_names routine, if you’re using Network framework [1] See the certificate_authorities field in Section 7.4.4 of RFC 5246, and equivalent features in other TLS versions. Self-Signed Certificates Self-signed certificates are an ongoing source of problems with TLS. There’s only one unequivocally correct place to use a self-signed certificate: the trusted anchor provided by a certificate authority. One place where a self-signed certificate might make sense is in a local environment, that is, securing a connection between peers without any centralised infrastructure. However, depending on the specific circumstances there may be a better option. TLS For Accessory Developers discusses this topic in detail. Finally, it’s common for folks to use self-signed certificates for testing. I’m not a fan of that approach. Rather, I recommend the approach described in QA1948 HTTPS and Test Servers. For advice on how to set that up using just your Mac, see TN2326 Creating Certificates for TLS Testing. TLS Standards RFC 6101 The Secure Sockets Layer (SSL) Protocol Version 3.0 (historic) RFC 2246 The TLS Protocol Version 1.0 RFC 4346 The Transport Layer Security (TLS) Protocol Version 1.1 RFC 5246 The Transport Layer Security (TLS) Protocol Version 1.2 RFC 8446 The Transport Layer Security (TLS) Protocol Version 1.3 RFC 4347 Datagram Transport Layer Security RFC 6347 Datagram Transport Layer Security Version 1.2 RFC 9147 The Datagram Transport Layer Security (DTLS) Protocol Version 1.3 Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" Revision History: 2025-11-21 Clearly defined the terms TLS-PKI and TLS-PSK. 2024-03-19 Adopted the term mutual TLS in preference to client certificate authentication throughout, because the latter feeds into the ongoing certificate versus digital identity confusion. Defined the term client identity. Added the Self-Signed Certificates section. Made other minor editorial changes. 2023-02-28 Added an explanation mTLS acceptable certificate authorities. 2022-12-02 Added links to the DTLS RFCs. 2022-08-24 Added links to the TLS RFCs. Made other minor editorial changes. 2022-06-03 Added a link to TLS For Accessory Developers. 2021-02-26 Fixed the formatting. Clarified that ATS only applies to URLSession. Minor editorial changes. 2020-04-17 Updated the discussion of Subject Alternative Name to account for changes in the 2019 OS releases. Minor editorial updates. 2018-10-29 Minor editorial updates. 2016-11-11 First posted.
0
0
8.3k
Nov ’25
Mark the iOS app content not to be backed up when doing unencrypted backup in iTunes
Hi,is there an option to mark the file or folder or item stored in user defaults ... not to be backed up when doing unencrypted backup in iTunes?We are developing iOS app that contains sensitive data. But even if we enable Data Protection for the iOS app it can be backed up on mac unencrypted using iTunes. Is there a way to allow backing up content only if the backup is encrypted?
2
0
1.8k
Oct ’25
security add-trusted-cert asks password twice in some cases: The authorization was denied since no user interaction was possible
Hey devs, I have a really weird issue and at this point I cannot determine is it a Big Sur 11.1 or M1 issue or just some macOS settings issue. Short description programatically (from node, electron) I'd like to store x509 cert to keychain. I got the following error message: SecTrustSettingsSetTrustSettings: The authorization was denied since no user interaction was possible. (1) I could reproduce this issue on: a brand new mac mini with M1 chip and Big Sur 11.1 another brand new mac mini with M1 chip and Big Sur 11.1 a 2018 MacBook pro with Intel chip and Big Sur 11.1 I couldn't reproduce this issue on: 2020 MacBook pro with intel i9 chip and Big Sur 11.1 2020 MacBook pro with intel i9 chip and Big Sur 11.0 How am I trying to store the cert node test.js test.js const { exec } = require('child_process') exec( &#9;`osascript -e 'do shell script "security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /Users/kotapeter/ssl/testsite.local.crt" with prompt "Test APP wants to store SSL certification to keychain." with administrator privileges'`, &#9;(error, stdout, stderr) => { &#9;&#9;if (error) { &#9;&#9;&#9;console.log(error.stack) &#9;&#9;&#9;console.log(`Error code: ${error.code}`) &#9;&#9;&#9;console.log(`Signal received: ${error.signal}`) &#9;&#9;} &#9;&#9;console.log(`STDOUT: ${stdout}`) &#9;&#9;console.log(`STDERR: ${stderr}`) &#9;&#9;process.exit(1) &#9;} ) testsite.local.crt: ----BEGIN CERTIFICATE MIIDUzCCAjugAwIBAgIUD9xMnL73y7fuida5TXgmklLswsowDQYJKoZIhvcNAQEL BQAwGTEXMBUGA1UEAwwOdGVzdHNpdGUubG9jYWwwHhcNMjEwMTE3MTExODU1WhcN NDEwMTEyMTExODU1WjAZMRcwFQYDVQQDDA50ZXN0c2l0ZS5sb2NhbDCCASIwDQYJ KoZIhvcNAQEBBQADggEPADCCAQoCggEBANM08SDi06dvnyU1A6//BeEFd8mXsOpD QCbYEHX/Pz4jqaBYwVjD5pG7FkvDeUKZnEVyrsofjZ4Y1WAT8jxPMUi+jDlgNTiF jPVc4rA6hcGX6b70HjsCACmc8bZd+EU7gm4b5eL6exTsVzHc+lFz4eQFXgutYTL7 guDQE/gFHwqPkLvnfg3rgY31p3Hm/snL8NuD154iE9O1WuSxEjik65uOQaewZmJ9 ejJEuuEhMA8O9dXveJ71TMV5lqA//svDxBu3zXIxMqRy2LdzfROd+guLP6ZD3jUy cWi7GpF4yN0+rD/0aXFJVHzV6TpS9oqb14jynvn1AyVfBB9+VQVNwTsCAwEAAaOB kjCBjzAJBgNVHRMEAjAAMAsGA1UdDwQEAwIC9DA7BgNVHSUENDAyBggrBgEFBQcD AQYIKwYBBQUHAwIGCCsGAQUFBwMDBggrBgEFBQcDBAYIKwYBBQUHAwgwHQYDVR0O BBYEFDjAC2ObSbB59XyLW1YaD7bgY8ddMBkGA1UdEQQSMBCCDnRlc3RzaXRlLmxv Y2FsMA0GCSqGSIb3DQEBCwUAA4IBAQBsU6OA4LrXQIZDXSIZPsDhtA7YZWzbrpqP ceXPwBd1k9Yd9T83EdA00N6eoOWFzwnQqwqKxtYdl3x9JQ7ewhY2huH9DRtCGjiT m/GVU/WnNm4tUTuGU4FyjSTRi8bNUxTSF5PZ0U2/vFZ0d7T43NbLQAiFSxyfC1r6 qjKQCYDL92XeU61zJxesxy5hxVNrbDpbPnCUZpx4hhL0RHgG+tZBOlBuW4eq249O 0Ql+3ShcPom4hzfh975385bfwfUT2s/ovng67IuM9bLSWWe7U+6HbOEvzMIiqK94 YYPmOC62cdhOaZIJmro6lL7eFLqlYfLU4H52ICuntBxvOx0UBExn----END CERTIFICATE testsite.local.key: ----BEGIN RSA PRIVATE KEY MIIEpQIBAAKCAQEA0zTxIOLTp2+fJTUDr/8F4QV3yZew6kNAJtgQdf8/PiOpoFjB WMPmkbsWS8N5QpmcRXKuyh+NnhjVYBPyPE8xSL6MOWA1OIWM9VzisDqFwZfpvvQe OwIAKZzxtl34RTuCbhvl4vp7FOxXMdz6UXPh5AVeC61hMvuC4NAT+AUfCo+Qu+d+ DeuBjfWnceb+ycvw24PXniIT07Va5LESOKTrm45Bp7BmYn16MkS64SEwDw711e94 nvVMxXmWoD/+y8PEG7fNcjEypHLYt3N9E536C4s/pkPeNTJxaLsakXjI3T6sP/Rp cUlUfNXpOlL2ipvXiPKe+fUDJV8EH35VBU3BOwIDAQABAoIBAQDDGLJsiFqu3gMK IZCIcHCDzcM7Kq43l2uY9hkuhltrERJNle70CfHgSAtubOCETtT1qdwfxUnR8mqX 15T5dMW3xpxNG7vNvD/bHrQfyc9oZuV6iJGsPEreJaV5qg/+E9yFzatrIam0SCS7 YL6xovPU58hZzQxuRbo95LetcT2dSBY33+ttY7ayV/Lx7k6nh0xU6RmTPHyyr8m7 yHpoJoSxdT/xv5iBSZ8mM9/2Vzhr14SWipVuwVVhDSfbn8ngHpIoQDkaJLMpWr+m 4z3PqfftAwR6s6i96HnhYLnRir618TQh4B9IEngeEwCMn4XAzE3L+VTaKU1hg9el aMfXzPERAoGBAPa+sJ2p9eQsv0vCUUL8KeRWvwjDZRTd+YAIfpLMWrb0tMmrBM4V V0L2joF76kdDxt1SAlHoYCT/3Rn8EPmK0TN3MEskiXQ7v57iv+LZOZcpe0ppG/4A ZihF9+wUjFCDw4ymnRQD463535O6BgZV+rcZksFRD2AwvEjt1nYm93VXAoGBANsh AYM+FPmMnzebUMB0oGIkNkE9nVb9MPbQYZjEeOeHJqmt1Nl6xLuYBWTmWwCy7J4e QPtnuMCdO6C1kuOGjQPBFIpeyFMzll+E3hKzicumgCpt5U8nTZoKc/jZckRD7n3p lbYYgHOR3A/3GCDK5L3rwziWpSRAGMSCQylvkOC9AoGBAKLfZL3t/r3LO8rKTdGl mhF7oUYrlIGdtJ/q+4HzGr5B8URdeyJ9u8gb8B1Qqmi4OIDHLXjbpvtFWbFZTesq 0sTiHCK9z23GMsqyam9XbEh3vUZ082FK6iQTa3+OYMCU+XPSV0Vq+9NPaWGeHXP5 NTG/07t/wmKASQjq1fHP7vCpAoGBAK4254T4bqSYcF09Vk4savab46aq3dSzJ6KS uYVDbvxkLxDn6zmcqZybmG5H1kIP/p8XXoKCTBiW6Tk0IrxR1PsPHs2D3bCIax01 /XjQ1NTcYzlYdd8gWEoH1XwbJQWxHINummBTyowXguYOhVhM9t8n+eWbn1/atdZF 2i+vS3fhAoGAYKw6rkJfTSEswgBKlQFJImxVA+bgKsEwUti1aBaIA2vyIYWDeV10 G8hlUDlxvVkfwCJoy5zz6joGGO/REhqOkMbFRPseA50u2NQVuK5C+avUXdcILJHN zp0nC5eZpP1TC++uCboJxo5TIdbLL7GRwQfffgALRBpK12Vijs195cc=----END RSA PRIVATE KEY What I've already found If I run the following command from terminal It asks my password first in terminal and after that It asks my password again in OS password prompt. sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /Users/kotapeter/ssl/testsite.local.crt It looks like I'm getting the above error message because osascript hides the second password asking dialog. The cert always gets stored in keychain but when I get the error message the cert "Trust" value is not "Always Trust". References StackOverflow question: https://stackoverflow.com/questions/65699160/electron-import-x509-cert-to-local-keychain-macos-the-authorization-was-deni opened issue on sudo-prompt electron package: https://github.com/jorangreef/sudo-prompt/issues/137
14
0
20k
Oct ’25
App ID Prefix Change and Keychain Access
DTS regularly receives questions about how to preserve keychain items across an App ID change, and so I thought I’d post a comprehensive answer here for the benefit of all. If you have any questions or comments, please start a new thread here on the forums. Put it in the Privacy & Security > General subtopic and tag it with Security. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" App ID Prefix Change and Keychain Access The list of keychain access groups your app can access is determined by three entitlements. For the details, see Sharing Access to Keychain Items Among a Collection of Apps. If your app changes its App ID prefix, this list changes and you’re likely to lose access to existing keychain items. This situation crops up under two circumstances: When you migrate your app from using a unique App ID prefix to using your Team ID as its App ID prefix. When you transfer your app to another team. In both cases you have to plan carefully for this change. If you only learn about the problem after you’ve made the change, consider undoing the change to give you time to come up with a plan before continuing. Note On macOS, the information in this post only applies to the data protection keychain. For more information about the subtleties of the keychain on macOS, see On Mac Keychains. For more about App ID prefix changes, see Technote 2311 Managing Multiple App ID Prefixes and QA1726 Resolving the Potential Loss of Keychain Access warning. Migrate From a Unique App ID Prefix to Your Team ID Historically each app was assigned its own App ID prefix. This is no longer the case. Best practice is for apps to use their Team ID as their App ID prefix. This enables multiple neat features, including keychain item sharing and pasteboard sharing. If you have an app that uses a unique App ID prefix, consider migrating it to use your Team ID. This is a good thing in general, as long as you manage the migration process carefully. Your app’s keychain access group list is built from three entitlements: keychain-access-groups — For more on this, see Keychain Access Groups Entitlement. application-identifier (com.apple.application-identifier on macOS) com.apple.security.application-groups — For more on this, see App Groups Entitlement. Keycahin access groups from the third bullet are call app group identified keychain access groups, or AGI keychain access groups for short. IMPORTANT A macOS app can only use an AGI keychain access group if all of its entitlement claims are validated by a provisioning profile. See App Groups: macOS vs iOS: Working Towards Harmony for more about this concept. Keychain access groups from the first two bullets depend on the App ID prefix. If that changes, you lose access to any keychain items in those groups. WARNING Think carefully before using the keychain to store secrets that are the only way to access irreplaceable user data. While the keychain is very reliable, there are situations where a keychain item can be lost and it’s bad if it takes the user’s data with it. In some cases losing access to keychain items is not a big deal. For example, if your app uses the keychain to manage a single login credential, losing that is likely to be acceptable. The user can recover by logging in again. In other cases losing access to keychain items is unacceptable. For example, your app might manage access to dozens of different servers, each with unique login credentials. Your users will be grumpy if you require them to log in to all those servers again. In such situations you must carefully plan your migration. The key thing to understand is that an app group is tied to your team, not your App ID prefix, and thus your app retains access to AGI keychain access groups across an App ID prefix change. This suggests the following approach: Release a version of your app that moves keychain items from other keychain access groups to an AGI keychain access group. Give your users time to update to this new version, run it, and so move their keychain items. When you’re confident that the bulk of your users have done this, change your App ID prefix. The approach has one obvious caveat: It’s hard to judge how long to wait at step 2. Transfer Your App to Another Team Historically there was no supported way to maintain access to keychain items across an app transfer. That’s no longer the case, but you must still plan the transfer carefully. The overall approach is: Identify an app group ID to transfer. This could be an existing app group ID, but in many cases you’ll want to register a new app group ID solely for this purpose. Use the old team (the transferor) to release a version of your app that moves keychain items from other keychain access groups to the AGI keychain access group for this app group ID. Give your users time to update to this new version, run it, and so move their keychain items. When you’re confident that the bulk of your users have done this, initiate the app transfer. Once that’s complete, transfer the app group ID you selected in step 1. See App Store Connect Help > Transfer an app > Overview of app transfer > Apps using App Groups. Publish an update to your app from the new team (the transferee). When a user installs this version, it will have access to your app group, and hence your keychain items. WARNING Once you transfer the app group, the old team won’t be able to publish a new version of any app that uses this app group. That makes step 1 in the process critical. If you have an existing app group that’s used solely by the app being transferred — for example, an app group that you use to share state between the app and its app extensions — then choosing that app group ID makes sense. On the other hand, choosing the ID of an app group that’s share between this app and some unrelated app, one that’s not being transferred, would be bad, because any updates to that other app will lose access to the app group. There are some other significant caveats: The process doesn’t work for Mac apps because Mac apps that have ever used an app group can’t be transferred. See App Store Connect Help > Transfer an app > App transfer criteria. If and when that changes, you’ll need to choose an iOS-style app group ID for your AGI keychain access group. For more about the difference between iOS- and macOS-style app group IDs, see App Groups: macOS vs iOS: Working Towards Harmony. The current transfer process of app groups exposes a small window where some other team can ‘steal’ your app group ID. We have a bug on file to improve that process (r. 171616887). The process works best when transferring between two teams that are both under the control of the same entity. If that’s not the case, take steps to ensure that the old team transfers the app group in step 5. When you submit the app from the new team (step 6), App Store Connect will warn you about a potential loss of keychain access. That warning is talking about keychain items in normal keychain access groups. Items in an AGI keychain access group will still be accessible as long as you transfer the app group. Alternative Approaches for App Transfer In addition to the technique described in the previous section, there are a some alternative approaches you should at consider: Do nothing Do not transfer your app Get creative Do Nothing In this case the user loses all the secrets that your app stored in the keychain. This may be acceptable for certain apps. For example, if your app uses the keychain to manage a single login credential, losing that is likely to be acceptable. The user can recover by logging in again. Do Not Transfer Another option is to not transfer your app. Instead, ship a new version of the app from the new team and have the old app recommend that the user upgrade. There are a number of advantages to this approach. The first is that there’s absolutely no risk of losing any user data. The two apps are completely independent. The second advantage is that the user can install both apps on their device at the same time. This opens up a variety of potential migration paths. For example, you might ship an update to the old app with an export feature that saves the user’s state, including their secrets, to a suitably encrypted file, and then match that with an import facility on the new app. Finally, this approach offers flexible timing. The user can complete their migration at their leisure. However, there are a bunch of clouds to go with these silver linings: Your users might never migrate to the new app. If this is a paid app, or an app with in-app purchase, the user will have to buy things again. You lose the original app’s history, ratings, reviews, and so on. Get Creative Finally, you could attempt something creative. For example, you might: Publish a new version of the app that supports exporting the user’s state, including the secrets. Tell your users to do this, with a deadline. Transfer the app and then, when the deadline expires, publish the new version with an import feature. Frankly, this isn’t very practical. The problem is with step 2: There’s no good way to get all your users to do the export, and if they don’t do it before the deadline there’s no way to do it after. Revision History 2026-03-31 Rewrote the Transfer Your App to Another Team section to describe a new approach for preserving access to keychain items across app transfers. Moved the previous discussion into a new Alternative Approaches for App Transfer section. Clarified that a macOS program can now use an app group as a keychain access group as long as its entitlements are validated. Made numerous editorial changes. 2022-05-17 First posted.
0
0
8.5k
1d
Security Resources
General: Forums topic: Privacy & Security Apple Platform Security support document Developer > Security Enabling enhanced security for your app documentation article Creating enhanced security helper extensions documentation article Security Audit Thoughts forums post Cryptography: Forums tags: Security, Apple CryptoKit Security framework documentation Apple CryptoKit framework documentation Common Crypto man pages — For the full list of pages, run: % man -k 3cc For more information about man pages, see Reading UNIX Manual Pages. On Cryptographic Key Formats forums post SecItem attributes for keys forums post CryptoCompatibility sample code Keychain: Forums tags: Security Security > Keychain Items documentation TN3137 On Mac keychain APIs and implementations SecItem Fundamentals forums post SecItem Pitfalls and Best Practices forums post Investigating hard-to-reproduce keychain problems forums post App ID Prefix Change and Keychain Access forums post Smart cards and other secure tokens: Forums tag: CryptoTokenKit CryptoTokenKit framework documentation Mac-specific resources: Forums tags: Security Foundation, Security Interface Security Foundation framework documentation Security Interface framework documentation BSD Privilege Escalation on macOS Related: Networking Resources — This covers high-level network security, including HTTPS and TLS. Network Extension Resources — This covers low-level network security, including VPN and content filters. Code Signing Resources Notarisation Resources Trusted Execution Resources — This includes Gatekeeper. App Sandbox Resources Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com"
0
0
3.8k
Nov ’25
SecItem: Pitfalls and Best Practices
I regularly help developers with keychain problems, both here on DevForums and for my Day Job™ in DTS. Over the years I’ve learnt a lot about the API, including many pitfalls and best practices. This post is my attempt to collect that experience in one place. If you have questions or comments about any of this, put them in a new thread and apply the Security tag so that I see it. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" SecItem: Pitfalls and Best Practices It’s just four functions, how hard can it be? The SecItem API seems very simple. After all, it only has four function calls, how hard can it be? In reality, things are not that easy. Various factors contribute to making this API much trickier than it might seem at first glance. This post explains some of the keychain’s pitfalls and then goes on to explain various best practices. Before reading this, make sure you understand the fundamentals by reading its companion post, SecItem: Fundamentals. Pitfalls Lets start with some common pitfalls. Queries and Uniqueness Constraints The relationship between query dictionaries and uniqueness constraints is a major source of problems with the keychain API. Consider code like this: var copyResult: CFTypeRef? = nil let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecAttrGeneric: Data("SecItemHints".utf8), ] as NSMutableDictionary let err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { query[kSecValueData] = Data("opendoor".utf8) let err2 = SecItemAdd(query, nil) if err2 == errSecDuplicateItem { fatalError("… can you get here? …") } } Can you get to the fatal error? At first glance this might not seem possible because you’ve run your query and it’s returned errSecItemNotFound. However, the fatal error is possible because the query contains an attribute, kSecAttrGeneric, that does not contribute to the uniqueness. If the keychain contains a generic password whose service (kSecAttrService) and account (kSecAttrAccount) attributes match those supplied but whose generic (kSecAttrGeneric) attribute does not, the SecItemCopyMatching calls will return errSecItemNotFound. However, for a generic password item, of the attributes shown here, only the service and account attributes are included in the uniqueness constraint. If you try to add an item where those attributes match an existing item, the add will fail with errSecDuplicateItem even though the value of the generic attribute is different. The take-home point is that that you should study the attributes that contribute to uniqueness and use them in a way that’s aligned with your view of uniqueness. See the Uniqueness section of SecItem: Fundamentals for a link to the relevant documentation. Erroneous Attributes Each keychain item class supports its own specific set of attributes. For information about the attributes supported by a given class, see SecItem: Fundamentals. I regularly see folks use attributes that aren’t supported by the class they’re working with. For example, the kSecAttrApplicationTag attribute is only supported for key items (kSecClassKey). Using it with a certificate item (kSecClassCertificate) will cause, at best, a runtime error and, at worst, mysterious bugs. This is an easy mistake to make because: The ‘parameter block’ nature of the SecItem API means that the compiler won’t complain if you use an erroneous attribute. On macOS, the shim that connects to the file-based keychain ignores unsupported attributes. Imagine you want to store a certificate for a particular user. You might write code like this: let err = SecItemAdd([ kSecClass: kSecClassCertificate, kSecAttrApplicationTag: Data(name.utf8), kSecValueRef: cert, ] as NSDictionary, nil) The goal is to store the user’s name in the kSecAttrApplicationTag attribute so that you can get back their certificate with code like this: let err = SecItemCopyMatching([ kSecClass: kSecClassCertificate, kSecAttrApplicationTag: Data(name.utf8), kSecReturnRef: true, ] as NSDictionary, &copyResult) On iOS, and with the data protection keychain on macOS, both calls will fail with errSecNoSuchAttr. That makes sense, because the kSecAttrApplicationTag attribute is not supported for certificate items. Unfortunately, the macOS shim that connects the SecItem API to the file-based keychain ignores extraneous attributes. This results in some very bad behaviour: SecItemAdd works, ignoring kSecAttrApplicationTag. SecItemCopyMatching ignores kSecAttrApplicationTag, returning the first certificate that it finds. If you only test with a single user, everything seems to work. But, later on, when you try your code with multiple users, you might get back the wrong result depending on the which certificate the SecItemCopyMatching call happens to discover first. Ouch! Context Matters Some properties change behaviour based on the context. The value type properties are the biggest offender here, as discussed in the Value Type Subtleties section of SecItem: Fundamentals. However, there are others. The one that’s bitten me is kSecMatchLimit: In a query and return dictionary its default value is kSecMatchLimitOne. If you don’t supply a value for kSecMatchLimit, SecItemCopyMatching returns at most one item that matches your query. In a pure query dictionary its default value is kSecMatchLimitAll. For example, if you don’t supply a value for kSecMatchLimit, SecItemDelete will delete all items that match your query. This is a lesson that, once learnt, is never forgotten! Note Although this only applies to the data protection keychain. If you’re on macOS and targeting the file-based keychain, kSecMatchLimit always defaults to kSecMatchLimitOne (r. 105800863). Fun times! Digital Identities Aren’t Real A digital identity is the combination of a certificate and the private key that matches the public key within that certificate. The SecItem API has a digital identity keychain item class, namely kSecClassIdentity. However, the keychain does not store digital identities. When you add a digital identity to the keychain, the system stores its components, the certificate and the private key, separately, using kSecClassCertificate and kSecClassKey respectively. This has a number of non-obvious effects: Adding a certificate can ‘add’ a digital identity. If the new certificate happens to match a private key that’s already in the keychain, the keychain treats that pair as a digital identity. Likewise when you add a private key. Similarly, removing a certificate or private key can ‘remove’ a digital identity. Adding a digital identity will either add a private key, or a certificate, or both, depending on what’s already in the keychain. Removing a digital identity removes its certificate. It might also remove the private key, depending on whether that private key is used by a different digital identity. The system forms a digital identity by matching the kSecAttrApplicationLabel (klbl) attribute of the private key with the kSecAttrPublicKeyHash (pkhh) attribute of the certificate. If you add both items to the keychain and the system doesn’t form an identity, check the value of these attributes. For more information the key attributes, see SecItem attributes for keys. Keys Aren’t Stored in the Secure Enclave Apple platforms let you protect a key with the Secure Enclave (SE). The key is then hardware bound. It can only be used by that specific SE [1]. Earlier versions of the Protecting keys with the Secure Enclave article implied that SE-protected keys were stored in the SE itself. This is not true, and it’s caused a lot of confusion. For example, I once asked the keychain team “How much space does the SE have available to store keys?”, a question that’s complete nonsense once you understand how this works. In reality, SE-protected keys are stored in the standard keychain database alongside all your other keychain items. The difference is that the key is wrapped in such a way that only the SE can use it. So, the key is protected by the SE, not stored in the SE. A while back we updated the docs to clarify this point but the confusion persists. [1] Technically it’s that specific iteration of that specific SE. If you erase the device then the key material needed to use the key is erased and so the key becomes permanently useless. This is the sort of thing you’ll find explained in Apple Platform Security. Careful With that Shim, Mac Developer As explained in TN3137 On Mac keychain APIs and implementations, macOS has a shim that connects the SecItem API to either the data protection keychain or the file-based keychain depending on the nature of the request. That shim has limitations. Some of those are architectural but others are simply bugs in the shim. For some great examples, see the Investigating Complex Attributes section below. The best way to avoid problems like this is to target the data protection keychain. If you can’t do that, try to avoid exploring the outer reaches of the SecItem API. If you encounter a case that doesn’t make sense, try that same case with the data protection keychain. If it works there but fails with the file-based keychain, please do file a bug against the shim. It’ll be in good company. Here’s some known issues with the shim: It ignores unsupported attributes. See Erroneous Attributes, above, for more background on that. The shim can fan out to both the data protection and the file-based keychain. In that case it has to make a policy decision about how to handle errors. This results in some unexpected behaviour (r. 143405965). For example, if you call SecItemCopyMatching while the keychain is locked, the data protection keychain will fail with errSecInteractionNotAllowed (-25308). OTOH, it’s possible to query for the presence of items in the file-based keychain even when it’s locked. If you do that and there’s no matching item, the file-based keychain fails with errSecItemNotFound (-25300). When the shim gets these conflicting errors, it chooses to return the latter. Whether this is right or wrong depends on your perspective, but it’s certainly confusing, especially if you’re coming at this from the iOS side. If you call SecItemDelete without specifying a match limit (kSecMatchLimit), the data protection keychain deletes all matching items, whereas the file-based keychain just deletes a single match (r. 105800863). While these issue have all have bug numbers, there’s no guarantee that any of them will be fixed. Fixing bugs like this is tricky because of binary compatibility concerns. Add-only Attributes Some attributes can only be set when you add an item. These attributes are usually associated with the scope of the item. For example, to protect an item with the Secure Enclave, supply the kSecAttrAccessControl attribute to the SecItemAdd call. Once you do that, however, you can’t change the attribute. Calling SecItemUpdate with a new kSecAttrAccessControl won’t work. Lost Keychain Items A common complaint from developers is that a seemingly minor update to their app has caused it to lose all of its keychain items. Usually this is caused by one of two problems: Entitlement changes Query dictionary confusion Access to keychain items is mediated by various entitlements, as described in Sharing access to keychain items among a collection of apps. If the two versions of your app have different entitlements, one version may not be able to ‘see’ items created by the other. Imagine you have an app with an App ID of SKMME9E2Y8.com.example.waffle-varnisher. Version 1 of your app is signed with the keychain-access-groups entitlement set to [ SKMME9E2Y8.groupA, SKMME9E2Y8.groupB ]. That makes its keychain access group list [ SKMME9E2Y8.groupA, SKMME9E2Y8.groupB, SKMME9E2Y8.com.example.waffle-varnisher ]. If this app creates a new keychain item without specifying kSecAttrAccessGroup, the system places the item into SKMME9E2Y8.groupA. If version 2 of your app removes SKMME9E2Y8.groupA from the keychain-access-groups, it’ll no longer be able to see the keychain items created by version 1. You’ll also see this problem if you change your App ID prefix, as described in App ID Prefix Change and Keychain Access. IMPORTANT When checking for this problem, don’t rely on your .entitlements file. There are many steps between it and your app’s actual entitlements. Rather, run codesign to dump the entitlements of your built app: % codesign -d --entitlements - /path/to/your.app Lost Keychain Items, Redux Another common cause of lost keychain items is confusion about query dictionaries, something discussed in detail in this post and SecItem: Fundamentals. If SecItemCopyMatching isn’t returning the expected item, add some test code to get all the items and their attributes. For example, to dump all the generic password items, run code like this: func dumpGenericPasswords() throws { let itemDicts = try secCall { SecItemCopyMatching([ kSecClass: kSecClassGenericPassword, kSecMatchLimit: kSecMatchLimitAll, kSecReturnAttributes: true, ] as NSDictionary, $0) } as! [[String: Any]] print(itemDicts) } Then compare each item’s attributes against the attributes you’re looking for to see why there was no match. Data Protection and Background Execution Keychain items are subject to data protection. Specifically, an item may or may not be accessible depending on whether specific key material is available. For an in-depth discussion of how this works, see Apple Platform Security. Note This section focuses on iOS but you’ll see similar effects on all Apple platforms. On macOS specifically, the contents of this section only apply to the data protection keychain. The keychain supports three data protection levels: kSecAttrAccessibleWhenUnlocked kSecAttrAccessibleAfterFirstUnlock kSecAttrAccessibleAlways Note There are additional data protection levels, all with the ThisDeviceOnly suffix. Understanding those is not necessary to understanding this pitfall. Each data protection level describes the lifetime of the key material needed to work with items protected in that way. Specifically: The key material needed to work with a kSecAttrAccessibleWhenUnlocked item comes and goes as the user locks and unlocks their device. The key material needed to work with a kSecAttrAccessibleAfterFirstUnlock item becomes available when the device is first unlocked and remains available until the device restarts. The default data protection level is kSecAttrAccessibleWhenUnlocked. If you add an item to the keychain and don’t specify a data protection level, this is what you get [1]. To specify a data protection level when you add an item to the keychain, apply the kSecAttrAccessible attribute. Alternatively, embed the access level within a SecAccessControl object and apply that using the kSecAttrAccessControl attribute. IMPORTANT It’s best practice to set these attributes when you add the item and then never update them. See Add-only Attributes, above, for more on that. If you perform an operation whose data protection is incompatible with the currently available key material, that operation fails with errSecInteractionNotAllowed [2]. There are four fundamental keychain operations, discussed in the SecItem: Fundamentals, and each interacts with data protection in a different way: Copy — If you attempt to access a keychain item whose key material is unavailable, SecItemCopyMatching fails with errSecInteractionNotAllowed. This is an obvious result; the whole point of data protection is to enforce this security policy. Add — If you attempt to add a keychain item whose key material is unavailable, SecItemAdd fails with errSecInteractionNotAllowed. This is less obvious. The reason why this fails is that the system needs the key material to protect (by encryption) the keychain item, and it can’t do that if if that key material isn’t available. Update — If you attempt to update a keychain item whose key material is unavailable, SecItemUpdate fails with errSecInteractionNotAllowed. This result is an obvious consequence of the previous result. Delete — Deleting a keychain item, using SecItemDelete, doesn’t require its key material, and thus a delete will succeed when the item is otherwise unavailable. That last point is a significant pitfall. I regularly see keychain code like this: Read an item holding a critical user credential. If that works, use that credential. If it fails, delete the item and start from a ‘factory reset’ state. The problem is that, if your code ends up running in the background unexpectedly, step 1 fails with errSecInteractionNotAllowed and you turn around and delete the user’s credential. Ouch! Note Even if you didn’t write this code, you might have inherited it from a keychain wrapper library. See *Think Before Wrapping, below. There are two paths forward here: If you don’t expect this code to work in the background, check for the errSecInteractionNotAllowed error and non-destructively cancel the operation in that case. If you expect this code to be running in the background, switch to a different data protection level. WARNING For the second path, the most obvious fix is to move from kSecAttrAccessibleWhenUnlocked to kSecAttrAccessibleAfterFirstUnlock. However, this is not a panacea. It’s possible that your app might end up running before first unlock [3]. So, if you choose the second path, you must also make sure to follow the advice for the first path. You can determine whether the device is unlocked using the isProtectedDataAvailable property and its associated notifications. However, it’s best not to use this property as part of your core code, because such preflighting is fundamentally racy. Rather, perform the operation and handle the error gracefully. It might make sense to use isProtectedDataAvailable property as part of debugging, logging, and diagnostic code. [1] For file data protection there’s an entitlement (com.apple.developer.default-data-protection) that controls the default data protection level. There’s no such entitlement for the keychain. That’s actually a good thing! In my experience the file data protection entitlement is an ongoing source of grief. See this thread if you’re curious. [2] This might seem like an odd error but it’s actually pretty reasonable: The operation needs some key material that’s currently unavailable. Only a user action can provide that key material. But the data protection keychain will never prompt the user to unlock their device. Thus you get an error instead. [3] iOS generally avoids running third-party code before first unlock, but there are circumstances where that can happen. The obvious legitimate example of this is a VoIP app, where the user expects their phone to ring even if they haven’t unlocked it since the last restart. There are also other less legitimate examples of this, including historical bugs that caused apps to launch in the background before first unlock. Best Practices With the pitfalls out of the way, let’s talk about best practices. Less Painful Dictionaries I look at a lot of keychain code and it’s amazing how much of it is way more painful than it needs to be. The biggest offender here is the dictionaries. Here are two tips to minimise the pain. First, don’t use CFDictionary. It’s seriously ugly. While the SecItem API is defined in terms of CFDictionary, you don’t have to work with CFDictionary directly. Rather, use NSDictionary and take advantage of the toll-free bridge. For example, consider this CFDictionary code: CFTypeRef keys[4] = { kSecClass, kSecAttrService, kSecMatchLimit, kSecReturnAttributes, }; static const int kTen = 10; CFNumberRef ten = CFNumberCreate(NULL, kCFNumberIntType, &kTen); CFAutorelease(ten); CFTypeRef values[4] = { kSecClassGenericPassword, CFSTR("AYS"), ten, kCFBooleanTrue, }; CFDictionaryRef query = CFDictionaryCreate( NULL, keys, values, 4, &kCFTypeDictionaryKeyCallBacks, &kCFTypeDictionaryValueCallBacks ); Note This might seem rather extreme but I’ve literally seen code like this, and worse, while helping developers. Contrast this to the equivalent NSDictionary code: NSDictionary * query = @{ (__bridge NSString *) kSecClass: (__bridge NSString *) kSecClassGenericPassword, (__bridge NSString *) kSecAttrService: @"AYS", (__bridge NSString *) kSecMatchLimit: @10, (__bridge NSString *) kSecReturnAttributes: @YES, }; Wow, that’s so much better. Second, if you’re working in Swift, take advantage of its awesome ability to create NSDictionary values from Swift dictionary literals. Here’s the equivalent code in Swift: let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecMatchLimit: 10, kSecReturnAttributes: true, ] as NSDictionary Nice! Avoid Reusing Dictionaries I regularly see folks reuse dictionaries for different SecItem calls. For example, they might have code like this: var copyResult: CFTypeRef? = nil let dict = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecReturnData: true, ] as NSMutableDictionary var err = SecItemCopyMatching(dict, &copyResult) if err == errSecItemNotFound { dict[kSecValueData] = Data("opendoor".utf8) err = SecItemAdd(dict, nil) } This specific example will work, but it’s easy to spot the logic error. kSecReturnData is a return type property and it makes no sense to pass it to a SecItemAdd call whose second parameter is nil. I’m not sure why folks do this. I think it’s because they think that constructing dictionaries is expensive. Regardless, this pattern can lead to all sorts of weird problems. For example, it’s the leading cause of the issue described in the Queries and the Uniqueness Constraints section, above. My advice is that you use a new dictionary for each call. That prevents state from one call accidentally leaking into a subsequent call. For example, I’d rewrite the above as: var copyResult: CFTypeRef? = nil let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecReturnData: true, ] as NSMutableDictionary var err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { let add = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecValueData: Data("opendoor".utf8), ] as NSMutableDictionary err = SecItemAdd(add, nil) } It’s a bit longer, but it’s much easier to track the flow. And if you want to eliminate the repetition, use a helper function: func makeDict() -> NSMutableDictionary { [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", ] as NSMutableDictionary } var copyResult: CFTypeRef? = nil let query = makeDict() query[kSecReturnData] = true var err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { let add = makeDict() query[kSecValueData] = Data("opendoor".utf8) err = SecItemAdd(add, nil) } Think Before Wrapping A lot of folks look at the SecItem API and immediately reach for a wrapper library. A keychain wrapper library might seem like a good idea but there are some serious downsides: It adds another dependency to your project. Different subsystems within your project may use different wrappers. The wrapper can obscure the underlying API. Indeed, its entire raison d’être is to obscure the underlying API. This is problematic if things go wrong. I regularly talk to folks with hard-to-debug keychain problems and the conversation goes something like this: Quinn: What attributes do you use in the query dictionary? J R Developer: What’s a query dictionary? Quinn: OK, so what error are you getting back? J R Developer: It throws WrapperKeychainFailedError. That’s not helpful )-: If you do use a wrapper, make sure it has diagnostic support that includes the values passed to and from the SecItem API. Also make sure that, when it fails, it returns an error that includes the underlying keychain error code. These benefits will be particularly useful if you encounter a keychain problem that only shows up in the field. Wrappers must choose whether to be general or specific. A general wrapper may be harder to understand than the equivalent SecItem calls, and it’ll certainly contain a lot of complex code. On the other hand, a specific wrapper may have a model of the keychain that doesn’t align with your requirements. I recommend that you think twice before using a keychain wrapper. Personally I find the SecItem API relatively easy to call, assuming that: I use the techniques shown in Less Painful Dictionaries, above, to avoid having to deal with CFDictionary. I use my secCall(…) helpers to simplify error handling. For the code, see Calling Security Framework from Swift. If you’re not prepared to take the SecItem API neat, consider writing your own wrapper, one that’s tightly focused on the requirements of your project. For example, in my VPN apps I use the wrapper from this post, which does exactly what I need in about 100 lines of code. Prefer to Update Of the four SecItem functions, SecItemUpdate is the most neglected. Rather than calling SecItemUpdate I regularly see folks delete and then re-add the item. This is a shame because SecItemUpdate has some important benefits: It preserves persistent references. If you delete and then re-add the item, you get a new item with a new persistent reference. It’s well aligned with the fundamental database nature of the keychain. It forces you to think about which attributes uniquely identify your item and which items can be updated without changing the item’s identity. Understand These Key Attributes Key items have a number of attributes that are similarly named, and it’s important to keep them straight. I created a cheat sheet for this, namely, SecItem attributes for keys. You wouldn’t believe how often I consult this! Investigating Complex Attributes Some attributes have values where the format is not obvious. For example, the kSecAttrIssuer attributed is documented as: The corresponding value is of type CFData and contains the X.500 issuer name of a certificate. What exactly does that mean? If I want to search the keychain for all certificates issued by a specific certificate authority, what value should I supply? One way to figure this out is to add a certificate to the keychain, read the attributes back, and then dump the kSecAttrIssuer value. For example: let cert: SecCertificate = … let attrs = try secCall { SecItemAdd([ kSecValueRef: cert, kSecReturnAttributes: true, ] as NSDictionary, $0) } as! [String: Any] let issuer = attrs[kSecAttrIssuer as String] as! NSData print((issuer as NSData).debugDescription) // prints: <3110300e 06035504 030c074d 6f757365 4341310b 30090603 55040613 024742> Those bytes represent the contents of a X.509 Name ASN.1 structure with DER encoding. This is without the outer SEQUENCE element, so if you dump it as ASN.1 you’ll get a nice dump of the first SET and then a warning about extra stuff at the end of the file: % xxd issuer.asn1 00000000: 3110 300e 0603 5504 030c 074d 6f75 7365 1.0...U....Mouse 00000010: 4341 310b 3009 0603 5504 0613 0247 42 CA1.0...U....GB % dumpasn1 -p issuer.asn1 SET { SEQUENCE { OBJECT IDENTIFIER commonName (2 5 4 3) UTF8String 'MouseCA' } } Warning: Further data follows ASN.1 data at position 18. Note For details on the Name structure, see section 4.1.2.4 of RFC 5280. Amusingly, if you run the same test against the file-based keychain you’ll… crash. OK, that’s not amusing. It turns out that the code above doesn’t work when targeting the file-based keychain because SecItemAdd doesn’t return a dictionary but rather an array of dictionaries (r. 21111543). Once you get past that, however, you’ll see it print: <301f3110 300e0603 5504030c 074d6f75 73654341 310b3009 06035504 06130247 42> Which is different! Dumping it as ASN.1 shows that it’s the full Name structure, including the outer SEQUENCE element: % xxd issuer-file-based.asn1 00000000: 301f 3110 300e 0603 5504 030c 074d 6f75 0.1.0...U....Mou 00000010: 7365 4341 310b 3009 0603 5504 0613 0247 seCA1.0...U....G 00000020: 42 B % dumpasn1 -p issuer-file-based.asn1 SEQUENCE { SET { SEQUENCE { OBJECT IDENTIFIER commonName (2 5 4 3) UTF8String 'MouseCA' } } SET { SEQUENCE { OBJECT IDENTIFIER countryName (2 5 4 6) PrintableString 'GB' } } } This difference in behaviour between the data protection and file-based keychains is a known bug (r. 26391756) but in this case it’s handy because the file-based keychain behaviour makes it easier to understand the data protection keychain behaviour. Import, Then Add It’s possible to import data directly into the keychain. For example, you might use this code to add a certificate: let certData: Data = … try secCall { SecItemAdd([ kSecClass: kSecClassCertificate, kSecValueData: certData, ] as NSDictionary, nil) } However, it’s better to import the data and then add the resulting credential reference. For example: let certData: Data = … let cert = try secCall { SecCertificateCreateWithData(nil, certData as NSData) } try secCall { SecItemAdd([ kSecValueRef: cert, ] as NSDictionary, nil) } There are two advantages to this: If you get an error, you know whether the problem was with the import step or the add step. It ensures that the resulting keychain item has the correct attributes. This is especially important for keys. These can be packaged in a wide range of formats, so it’s vital to know whether you’re interpreting the key data correctly. I see a lot of code that adds key data directly to the keychain. That’s understandable because, back in the day, this was the only way to import a key on iOS. Fortunately, that’s not been the case since the introduction of SecKeyCreateWithData in iOS 10 and aligned releases. For more information about importing keys, see Importing Cryptographic Keys. App Groups on the Mac Sharing access to keychain items among a collection of apps explains that three entitlements determine your keychain access: keychain-access-groups application-identifier (com.apple.application-identifier on macOS) com.apple.security.application-groups In the discussion of com.apple.security.application-groups it says: Starting in iOS 8, the array of strings given by this entitlement also extends the list of keychain access groups. That’s true, but it’s also potentially misleading. This affordance only works on iOS and its child platforms. It doesn’t work on macOS. That’s because app groups work very differently on macOS than they do on iOS. For all the details, see App Groups: macOS vs iOS: Working Towards Harmony. However, the take-home point is that, when you use the data protection keychain on macOS, your keychain access group list is built from keychain-access-groups and com.apple.application-identifier. Revision History 2025-06-29 Added the Data Protection and Background Execution section. Made other minor editorial changes. 2025-02-03 Added another specific example to the Careful With that Shim, Mac Developer section. 2025-01-29 Added somes specific examples to the Careful With that Shim, Mac Developer section. 2025-01-23 Added the Import, Then Add section. 2024-08-29 Added a discussion of identity formation to the Digital Identities Aren’t Real section. 2024-04-11 Added the App Groups on the Mac section. 2023-10-25 Added the Lost Keychain Items and Lost Keychain Items, Redux sections. 2023-09-22 Made minor editorial changes. 2023-09-12 Fixed various bugs in the revision history. Added the Erroneous Attributes section. 2023-02-22 Fixed the link to the VPNKeychain post. Corrected the name of the Context Matters section. Added the Investigating Complex Attributes section. 2023-01-28 First posted.
0
0
3.9k
Jun ’25
App Group Not working as intended after updating to macOS 15 beta.
I have an app (currently not released on App Store) which runs on both iOS and macOS. The app has widgets for both iOS and macOS which uses user preference (set in app) into account while showing data. Before upgrading to macOS 15 (until Sonoma) widgets were working fine and app was launching correctly, but after upgrading to macOS 15 Sequoia, every time I launch the app it give popup saying '“Kontest” would like to access data from other apps. Keeping app data separate makes it easier to manage your privacy and security.' and also widgets do not get user preferences and throw the same type of error on Console application when using logging. My App group for both iOS and macOS is 'group.com.xxxxxx.yyyyy'. I am calling it as 'UserDefaults(suiteName: Constants.userDefaultsGroupID)!.bool(forKey: "shouldFetchAllEventsFromCalendar")'. Can anyone tell, what am I doing wrong here?
26
9
5k
Oct ’25
`cp` ( & friends ) silent loss of extended attributes & file flags
Since the introduction of the siblings / and /System/Volumes/Data architecture, some very basic, critical commands seems to have a broken behaviour ( cp, rsync, tar, cpio…). As an example, ditto which was introduced more than 10 years ago to integrate correctly all the peculiarity of HFS Apple filesystem as compared to the UFS Unix filesystem is not behaving correctly. For example, from man ditto: --rsrc Preserve resource forks and HFS meta-data. ditto will store this data in Carbon-compatible ._ AppleDouble files on filesystems that do not natively support resource forks. As of Mac OS X 10.4, --rsrc is default behavior. [...] --extattr Preserve extended attributes (requires --rsrc). As of Mac OS X 10.5, --extattr is the default. and nonetheless: # ls -@delO /private/var/db/ConfigurationProfiles/Store drwx------@ 5 root wheel datavault 160 Jan 20 2024 /private/var/db/ConfigurationProfiles/Store                            ********* com.apple.rootless 28 *************************** # mkdir tmp # ditto /private/var/db/ConfigurationProfiles tmp ditto: /Users/alice/Security/Admin/Apple/APFS/tmp/Settings: Operation not permitted ditto: /Users/alice/Security/Admin/Apple/APFS/tmp/Store: Operation not permitted # ls -@delO tmp/Store drwx------ 5 root wheel - 160 Aug 8 13:55 tmp/Store                            * # The extended attribute on copied directory Store is empty, the file flags are missing, not preserved as documented and as usual behaviour of ditto was since a long time ( macOS 10.5 ). cp, rsync, tar, cpio exhibit the same misbehaviour. But I was using ditto to be sure to avoid any incompatibility with the Apple FS propriaitary modifications. As a consequence, all backup scripts and applications are failing more or less silently, and provide corrupted copies of files or directories. ( I was here investigating why one of my security backup shell script was making corrupted backups, and only on macOS ). How to recover the standard behaviour --extattr working on modern macOS?
4
0
1.1k
Feb ’26
MFA MacOS At ScreenSaver (Lock Screen).
Hi , I did The MFA(2FA) of Email OTP For MacOS Login Screen using, Authorization Plugin, Using This git hub project. It is working For Login Screen , Im trying to Add The Same plugin for LockScreen but it is not working at lock Screen , Below is the reffrense theard For The issue , https://developer.apple.com/forums/thread/127614, please Share The Code that should Present the NSwindow at Screen Saver (Lock Screen) MacOS .
3
0
972
5d
setCodeSigningRequirement seems not to work in new Service Management API setup.
I have developed a sample app following the example found Updating your app package installer to use the new Service Management API and referring this discussion on XPC Security. The app is working fine, I have used Swift NSXPCConnection in favour of xpc_connection_create_mach_service used in the example. (I am running app directly from Xcode) I am trying to set up security requirements for the client connection using setCodeSigningRequirement on the connection instance. But it fails for even basic requirement connection.setCodeSigningRequirement("anchor apple"). Error is as follows. cannot open file at line 46986 of [554764a6e7] os_unix.c:46986: (0) open(/private/var/db/DetachedSignatures) - Undefined error: 0 xpc_support_check_token: anchor apple error: Error Domain=NSOSStatusErrorDomain Code=-67050 "(null)" status: -67050 I have used codesign -d --verbose=4 /path/to/executable to check the attributes I do get them in the terminal. Other way round, I have tried XPC service provider sending back process id (pid) with each request, and I am probing this id to get attributes using this code which gives all the details. func inspectCodeSignature(ofPIDString pidString: String) { guard let pid = pid_t(pidString) else { print("Invalid PID string: \(pidString)") return } let attributes = [kSecGuestAttributePid: pid] as CFDictionary var codeRef: SecCode? let status = SecCodeCopyGuestWithAttributes(nil, attributes, [], &codeRef) guard status == errSecSuccess, let code = codeRef else { print("Failed to get SecCode for PID \(pid) (status: \(status))") return } var staticCode: SecStaticCode? let staticStatus = SecCodeCopyStaticCode(code, [], &staticCode) guard staticStatus == errSecSuccess, let staticCodeRef = staticCode else { print("Failed to get SecStaticCode (status: \(staticStatus))") return } var infoDict: CFDictionary? if SecCodeCopySigningInformation(staticCodeRef, SecCSFlags(rawValue: kSecCSSigningInformation), &infoDict) == errSecSuccess, let info = infoDict as? [String: Any] { print("🔍 Code Signing Info for PID \(pid):") print("• Identifier: \(info["identifier"] ?? "N/A")") print("• Team ID: \(info["teamid"] ?? "N/A")") if let entitlements = info["entitlements-dict"] as? [String: Any] { print("• Entitlements:") for (key, value) in entitlements { print(" - \(key): \(value)") } } } else { print("Failed to retrieve signing information.") } var requirement: SecRequirement? if SecRequirementCreateWithString("anchor apple" as CFString, [], &requirement) == errSecSuccess, let req = requirement { let result = SecStaticCodeCheckValidity(staticCodeRef, [], req) if result == errSecSuccess { print("Signature is trusted (anchor apple)") } else { print("Signature is NOT trusted by Apple (failed anchor check)") } } var infoDict1: CFDictionary? let signingStatus = SecCodeCopySigningInformation(staticCodeRef, SecCSFlags(rawValue: kSecCSSigningInformation), &infoDict1) guard signingStatus == errSecSuccess, let info = infoDict1 as? [String: Any] else { print("Failed to retrieve signing information.") return } print("🔍 Signing Info for PID \(pid):") for (key, value) in info.sorted(by: { $0.key < $1.key }) { print("• \(key): \(value)") } } If connection.setCodeSigningRequirement does not works I plan to use above logic as backup. Q: Please advise is there some setting required to be enabled or I have to sign code with some flags enabled. Note: My app is not running in a Sandbox or Hardened Runtime, which I want.
12
0
378
Apr ’25
Auth Plugin Timeout Issue During Screen Unlock
Hi! We are developing an authentication plugin for macOS that integrates with the system's authentication flow. The plugin is designed to prompt the user for approval via a push notification in our app before allowing access. The plugin is added as the first mechanism in the authenticate rule, followed by the default builtin:authenticate as a fallback. When the system requests authentication (e.g., during screen unlock), our plugin successfully displays the custom UI and sends a push notification to the user's device. However, I've encountered the following issue: If the user does not approve the push notification within ~30 seconds, the system resets the screen lock (expected behavior). If the user approves the push notification within approximately 30 seconds but doesn’t start entering their password before the timeout expires, the system still resets the screen lock before they can enter their password, effectively canceling the session. What I've Tried: Attempted to imitate mouse movement after the push button was clicked to keep the session active. Created a display sleep prevention assertion using IOKit to prevent the screen from turning off. Used the caffeinate command to keep the display and system awake. Tried setting the result as allow for the authorization request and passing an empty password to prevent the display from turning off. I also checked the system logs when this issue occurred and found the following messages: ___loginwindow: -[LWScreenLock (Private) askForPasswordSecAgent] | localUser = >timeout loginwindow: -[LWScreenLock handleUnlockResult:] _block_invoke | ERROR: Unexpected _lockRequestedBy of:7 sleeping screen loginwindow: SleepDisplay | enter powerd: Process (loginwindow) is requesting display idle___ These messages suggest that the loginwindow process encounters a timeout condition, followed by the display entering sleep mode. Despite my attempts to prevent this behavior, the screen lock still resets prematurely. Questions: Is there a documented (or undocumented) system timeout for the entire authentication flow during screen unlock that I cannot override? Are there any strategies for pausing or extending the authentication timeout to allow for complex authentication flows like push notifications? Any guidance or insights would be greatly appreciated. Thank you!
3
2
351
Jun ’25
Login Keychain Access Autmation
I have been trying to find a way to be able to sign some data with private key of an identity in login keychain without raising any prompts. I am able to do this with system keychain (obviously with correct permissions and checks) but not with login keychain. It always ends up asking user for their login password. Here is how the code looks, roughly, NSDictionary *query = @{ (__bridge id)kSecClass: (__bridge id)kSecClassIdentity, (__bridge id)kSecReturnRef: @YES, (__bridge id)kSecMatchLimit: (__bridge id)kSecMatchLimitAll }; CFTypeRef result = NULL; OSStatus status = SecItemCopyMatching((__bridge CFDictionaryRef)query, (CFTypeRef *)&amp;amp;result); NSArray *identities = ( NSArray *)result; SecIdentityRef identity = NULL; for (id _ident in identities) { // pick one as required } SecKeyRef privateKey = NULL; OSStatus status = SecIdentityCopyPrivateKey(identity, &amp;amp;privateKey); NSData *strData = [string dataUsingEncoding:NSUTF8StringEncoding]; unsigned char hash[CC_SHA256_DIGEST_LENGTH]; CC_SHA256(strData.bytes, (CC_LONG)strData.length, hash); NSData *digestData = [NSData dataWithBytes:hash length:CC_SHA256_DIGEST_LENGTH]; CFErrorRef cfError = NULL; NSData *signature = (__bridge_transfer NSData *)SecKeyCreateSignature(privateKey, kSecKeyAlgorithmRSASignatureDigestPKCS1v15SHA256, (__bridge CFDataRef)digestData, &amp;amp;cfError); Above code raises these system logs in console default 08:44:52.781024+0000 securityd client is valid, proceeding default 08:44:52.781172+0000 securityd code requirement check failed (-67050), client is not Apple-signed default 08:44:52.781233+0000 securityd displaying keychain prompt for /Applications/Demo.app(81692) If the key is in login keychain, is there any way to do SecKeyCreateSignature without raising prompts? What does client is not Apple-signed mean? PS: Identities are pre-installed either manually or via some device management solution, the application is not installing them.
3
0
178
Apr ’25
Unsandboxed app can't modify other app
I work for Brave, a browser with ~80M users. We want to introduce a new system for automatic updates called Omaha 4 (O4). It's the same system that powers automatic updates in Chrome. O4 runs as a separate application on users' systems. For Chrome, this works as follows: An app called GoogleUpdater.app regularly checks for updates in the background. When a new version is found, then GoogleUpdater.app installs it into Chrome's installation directory /Applications/Google Chrome.app. But consider what this means: A separate application, GoogleUpdater.app, is able to modify Google Chrome.app. This is especially surprising because, for example, the built-in Terminal.app is not able to modify Google Chrome.app. Here's how you can check this for yourself: (Re-)install Chrome with its DMG installer. Run the following command in Terminal: mkdir /Applications/Google\ Chrome.app/test. This works. Undo the command: rm -rf /Applications/Google\ Chrome.app/test Start Chrome and close it again. mkdir /Applications/Google\ Chrome.app/test now fails with "Operation not permitted". (These steps assume that Terminal does not have Full Disk Access and System Integrity Protection is enabled.) In other words, once Chrome was started at least once, another application (Terminal in this case) is no longer allowed to modify it. But at the same time, GoogleUpdater.app is able to modify Chrome. It regularly applies updates to the browser. For each update, this process begins with an mkdir call similarly to the one shown above. How is this possible? What is it in macOS that lets GoogleUpdater.app modify Chrome, but not another app such as Terminal? Note that Terminal is not sandboxed. I've checked that it's not related to codesigning or notarization issues. In our case, the main application (Brave) and the updater (BraveUpdater) are signed and notarized with the same certificate and have equivalent requirements, entitlements and provisioning profiles as Chrome and GoogleUpdater. The error that shows up in the Console for the disallowed mkdir call is: kernel (Sandbox) System Policy: mkdir(8917) deny(1) file-write-create /Applications/Google Chrome.app/foo (It's a similar error when BraveUpdater tries to install a new version into /Applications/Brave Browser.app.) The error goes away when I disable System Integrity Protection. But of course, we cannot ask users to do that. Any help would be greatly appreciated.
4
0
310
May ’25
API: SecPKCS12Import; error code: -25264; error message: MAC verification failed during PKCS12 import (wrong password?)
Problem Statement: Pre-requisite is to generate a PKCS#12 file using openssl 3.x or above. Note: I have created a sample cert, but unable to upload it to this thread. Let me know if there is a different way I can upload. When trying to import a p12 certificate (generated using openssl 3.x) using SecPKCS12Import on MacOS (tried on Ventura, Sonoma, Sequoia). It is failing with the error code: -25264 and error message: MAC verification failed during PKCS12 import (wrong password?). I have tried importing in multiple ways through, Security Framework API (SecPKCS12Import) CLI (security import &lt;cert_name&gt; -k ~/Library/Keychains/login.keychain -P "&lt;password&gt;”) Drag and drop in to the Keychain Application All of them fail to import the p12 cert. RCA: The issues seems to be due to the difference in the MAC algorithm. The MAC algorithm used in the modern certs (by OpenSSL3 is SHA-256) which is not supported by the APPLE’s Security Framework. The keychain seems to be expecting the MAC algorithm to be SHA-1. Workaround: The current workaround is to convert the modern p12 cert to a legacy format (using openssl legacy provider which uses openssl 1.1.x consisting of insecure algorithms) which the SecPKCS12Import API understands. I have created a sample code using references from another similar thread (https://developer.apple.com/forums/thread/723242) from 2023. The steps to compile and execute the sample is mentioned in the same file. PFA the sample code by the name “pkcs12_modern_to_legacy_converter.cpp”. Also PFA a sample certificate which will help reproduce the issue by the name “modern_certificate.p12” whose password is “export”. Questions: Is there a fix on this issue? If yes, pls guide me through it; else, is it expected to be fixed in the future releases? Is there a different way to import the p12 cert which is resistant to the issue? This issue also poses a security concerns on using outdated cryptographic algorithms. Kindly share your thoughts. pkcs12_modern_to_legacy_converter.cpp
11
0
506
Apr ’25
Clang warning about 'xar_open' API deprecation in macOS 12.0. How to address/replace with a more approprite API?
Hello! We have code that extracts macOS Installer package (.pkg, .mpkg) signature information using APIs defined in <xar/xar.h> The code opens the package using ‘xar_open’ API like this. func open(file: String) throws(XarError) { xarfile = xar_open(file, READ) if xarfile == nil { throw .fileOpenError } } This code produces a clang warning in our CI build system when built for macOS 12 and up. 'xar_open' was deprecated in macOS 12.0: xar is a deprecated file format and should not be used. Question #1: What is the appropriate / more preferred way to extract signature information from an Installer package given that xar related APIs are deprecated? We use xar APIs to validate the package signature prior to installation to prevent packagers not signed by our team ID from being installed. Question #2: “xar is a deprecated file format and should not be used.”. Does this phrase refer to the file format that should be avoided or the API that extract signature information? We distribute our product using Developer ID method that using pkg/mpkg formats which I believe internally follow the same structure as xar files. I hope this message does not mean we should rethink the distribution method for our products. Thank you. Filed FB FB17148233 as well.
10
0
433
Apr ’25
How to Localize Biometric Prompt for SecKeyCreateSignature with Secure Enclave
I'm using Secure Enclave to generate and use a private key like this: let access = SecAccessControlCreateWithFlags(nil, kSecAttrAccessibleWhenUnlockedThisDeviceOnly, [.privateKeyUsage, .biometryAny], nil) let attributes: [String: Any] = [ kSecAttrKeyType as String: kSecAttrKeyTypeECSECPrimeRandom, kSecAttrKeySizeInBits as String: 256, kSecAttrTokenID as String: kSecAttrTokenIDSecureEnclave, kSecAttrAccessControl as String: access as Any, kSecAttrApplicationTag as String: "com.example.key".data(using: .utf8)!, kSecReturnRef as String: true ] let privateKey = SecKeyCreateRandomKey(attributes as CFDictionary, nil) Later, I use this key to sign a message: let signature = SecKeyCreateSignature(privateKey, .ecdsaSignatureMessageX962SHA256, dataToSign as CFData, nil) This prompts for biometric authentication, but shows the default system text. How can I customize or localize the biometric prompt (e.g., title, description, button text) shown during SecKeyCreateSignature? Thanks!
1
0
120
Apr ’25
iOS 18.4 key usage requirements fails TLS connections
iOS 18.4 introduced some requirements on the Key Usage of 802.1x server certificates, as described here. https://support.apple.com/en-us/121158 When using TLS_ECDHE_RSA or TLS_DHE_RSA cipher suites, 802.1X server certificates containing a Key Usage extension must have Digital Signature key usage set. When using the TLS_RSA cipher suite, 802.1X server certificates containing a Key Usage extension must have Key Encipherment key usage set. It reads like the change is supposed to affect 802.1x only. However, we have found out that the new restrictions are actually imposed on all TLS connections using the Network framework, including in Safari. Unlike other certificate errors which can be either ignored by users (as in Safari) or by code (via sec_protocol_options_set_verify_block), these new ones can't. Even if passing completion(true) in the TLS verification block, the connection still ends up in waiting state with error -9830: illegal parameter. I understand that these requirements are valid ones but as a generic TLS library I also expect that Network framework could at least allow overriding the behavior. The current treatment is not consistent with those on other certificate errors. Since I can't upload certificates, here is how to reproduce a certificate that fails. Create a OpenSSL config file test.cnf [ req ] default_bits = 2048 distinguished_name = dn x509_extensions = v3_ca prompt = no [ dn ] CN = example.com [ v3_ca ] subjectKeyIdentifier = hash authorityKeyIdentifier = keyid:always,issuer basicConstraints = CA:TRUE keyUsage = critical, keyCertSign, cRLSign Generate certificate and private key openssl req -x509 -new -nodes -keyout key.pem -out cert.pem -days 365 -config test.cnf And here is the client code to test. // Target server and port let host = NWEndpoint.Host("example.com") let port = NWEndpoint.Port("443")! // Configure insecure TLS options let tlsOptions = NWProtocolTLS.Options() sec_protocol_options_set_verify_block(tlsOptions.securityProtocolOptions, { _, _, completion in // Always trust completion(true) }, DispatchQueue.global()) let params = NWParameters(tls: tlsOptions) let connection = NWConnection(host: .init(host), port: .init(rawValue: port)!, using: params) connection.stateUpdateHandler = { newState in switch newState { case .ready: print("TLS connection established") case .failed(let error): print("Connection failed: \(error)") case .cancelled: print("Connection canceled") case .preparing: print("Connection preparing") case .waiting(let error): print("Connection waiting: \(error)") case .setup: print("Connection setup") default: break } } connection.start(queue: .global()) Output Connection preparing Connection waiting: -9830: illegal parameter Previously reported as FB17099740
5
0
302
Apr ’25
SecItem: Fundamentals
I regularly help developers with keychain problems, both here on DevForums and for my Day Job™ in DTS. Many of these problems are caused by a fundamental misunderstanding of how the keychain works. This post is my attempt to explain that. I wrote it primarily so that Future Quinn™ can direct folks here rather than explain everything from scratch (-: If you have questions or comments about any of this, put them in a new thread and apply the Security tag so that I see it. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" SecItem: Fundamentals or How I Learned to Stop Worrying and Love the SecItem API The SecItem API seems very simple. After all, it only has four function calls, how hard can it be? In reality, things are not that easy. Various factors contribute to making this API much trickier than it might seem at first glance. This post explains the fundamental underpinnings of the keychain. For information about specific issues, see its companion post, SecItem: Pitfalls and Best Practices. Keychain Documentation Your basic starting point should be Keychain Items. If your code runs on the Mac, also read TN3137 On Mac keychain APIs and implementations. Read the doc comments in <Security/SecItem.h>. In many cases those doc comments contain critical tidbits. When you read keychain documentation [1] and doc comments, keep in mind that statements specific to iOS typically apply to iPadOS, tvOS, and watchOS as well (r. 102786959). Also, they typically apply to macOS when you target the data protection keychain. Conversely, statements specific to macOS may not apply when you target the data protection keychain. [1] Except TN3137, which is very clear about this (-: Caveat Mac Developer macOS supports two different keychain implementations: the original file-based keychain and the iOS-style data protection keychain. IMPORTANT If you’re able to use the data protection keychain, do so. It’ll make your life easier. See the Careful With that Shim, Mac Developer section of SecItem: Pitfalls and Best Practices for more about this. TN3137 On Mac keychain APIs and implementations explains this distinction. It also says: The file-based keychain is on the road to deprecation. This is talking about the implementation, not any specific API. The SecItem API can’t be deprecated because it works with both the data protection keychain and the file-based keychain. However, Apple has deprecated many APIs that are specific to the file-based keychain, for example, SecKeychainCreate. TN3137 also notes that some programs, like launchd daemons, can’t use the file-based keychain. If you’re working on such a program then you don’t have to worry about the deprecation of these file-based keychain APIs. You’re already stuck with the file-based keychain implementation, so using a deprecated file-based keychain API doesn’t make things worse. The Four Freedoms^H^H^H^H^H^H^H^H Functions The SecItem API contains just four functions: SecItemAdd(_:_:) SecItemCopyMatching(_:_:) SecItemUpdate(_:_:) SecItemDelete(_:) These directly map to standard SQL database operations: SecItemAdd(_:_:) maps to INSERT. SecItemCopyMatching(_:_:) maps to SELECT. SecItemUpdate(_:_:) maps to UPDATE. SecItemDelete(_:) maps to DELETE. You can think of each keychain item class (generic password, certificate, and so on) as a separate SQL table within the database. The rows of that table are the individual keychain items for that class and the columns are the attributes of those items. Note Except for the digital identity class, kSecClassIdentity, where the values are split across the certificate and key tables. See Digital Identities Aren’t Real in SecItem: Pitfalls and Best Practices. This is not an accident. The data protection keychain is actually implemented as an SQLite database. If you’re curious about its structure, examine it on the Mac by pointing your favourite SQLite inspection tool — for example, the sqlite3 command-line tool — at the keychain database in ~/Library/Keychains/UUU/keychain-2.db, where UUU is a UUID. WARNING Do not depend on the location and structure of this file. These have changed in the past and are likely to change again in the future. If you embed knowledge of them into a shipping product, it’s likely that your product will have binary compatibility problems at some point in the future. The only reason I’m mentioning them here is because I find it helpful to poke around in the file to get a better understanding of how the API works. For information about which attributes are supported by each keychain item class — that is, what columns are in each table — see the Note box at the top of Item Attribute Keys and Values. Alternatively, look at the Attribute Key Constants doc comment in <Security/SecItem.h>. Uniqueness A critical part of the keychain model is uniqueness. How does the keychain determine if item A is the same as item B? It turns out that this is class dependent. For each keychain item class there is a set of attributes that form the uniqueness constraint for items of that class. That is, if you try to add item A where all of its attributes are the same as item B, the add fails with errSecDuplicateItem. For more information, see the errSecDuplicateItem page. It has lists of attributes that make up this uniqueness constraint, one for each class. These uniqueness constraints are a major source of confusion, as discussed in the Queries and the Uniqueness Constraints section of SecItem: Pitfalls and Best Practices. Parameter Blocks Understanding The SecItem API is a classic ‘parameter block’ API. All of its inputs are dictionaries, and you have to know which properties to set in each dictionary to achieve your desired result. Likewise for when you read properties in output dictionaries. There are five different property groups: The item class property, kSecClass, determines the class of item you’re operating on: kSecClassGenericPassword, kSecClassCertificate, and so on. The item attribute properties, like kSecAttrAccessGroup, map directly to keychain item attributes. The search properties, like kSecMatchLimit, control how the system runs a query. The return type properties, like kSecReturnAttributes, determine what values the query returns. The value type properties, like kSecValueRef perform multiple duties, as explained below. There are other properties that perform a variety of specific functions. For example, kSecUseDataProtectionKeychain tells macOS to use the data protection keychain instead of the file-based keychain. These properties are hard to describe in general; for the details, see the documentation for each such property. Inputs Each of the four SecItem functions take dictionary input parameters of the same type, CFDictionary, but these dictionaries are not the same. Different dictionaries support different property groups: The first parameter of SecItemAdd(_:_:) is an add dictionary. It supports all property groups except the search properties. The first parameter of SecItemCopyMatching(_:_:) is a query and return dictionary. It supports all property groups. The first parameter of SecItemUpdate(_:_:) is a pure query dictionary. It supports all property groups except the return type properties. Likewise for the only parameter of SecItemDelete(_:). The second parameter of SecItemUpdate(_:_:) is an update dictionary. It supports the item attribute and value type property groups. Outputs Two of the SecItem functions, SecItemAdd(_:_:) and SecItemCopyMatching(_:_:), return values. These output parameters are of type CFTypeRef because the type of value you get back depends on the return type properties you supply in the input dictionary: If you supply a single return type property, except kSecReturnAttributes, you get back a value appropriate for that return type. If you supply multiple return type properties or kSecReturnAttributes, you get back a dictionary. This supports the item attribute and value type property groups. To get a non-attribute value from this dictionary, use the value type property that corresponds to its return type property. For example, if you set kSecReturnPersistentRef in the input dictionary, use kSecValuePersistentRef to get the persistent reference from the output dictionary. In the single item case, the type of value you get back depends on the return type property and the keychain item class: For kSecReturnData you get back the keychain item’s data. This makes most sense for password items, where the data holds the password. It also works for certificate items, where you get back the DER-encoded certificate. Using this for key items is kinda sketchy. If you want to export a key, called SecKeyCopyExternalRepresentation. Using this for digital identity items is nonsensical. For kSecReturnRef you get back an object reference. This only works for keychain item classes that have an object representation, namely certificates, keys, and digital identities. You get back a SecCertificate, a SecKey, or a SecIdentity, respectively. For kSecReturnPersistentRef you get back a data value that holds the persistent reference. Value Type Subtleties There are three properties in the value type property group: kSecValueData kSecValueRef kSecValuePersistentRef Their semantics vary based on the dictionary type. For kSecValueData: In an add dictionary, this is the value of the item to add. For example, when adding a generic password item (kSecClassGenericPassword), the value of this key is a Data value containing the password. This is not supported in a query dictionary. In an update dictionary, this is the new value for the item. For kSecValueRef: In add and query dictionaries, the system infers the class property and attribute properties from the supplied object. For example, if you supply a certificate object (SecCertificate, created using SecCertificateCreateWithData), the system will infer a kSecClass value of kSecClassCertificate and various attribute values, like kSecAttrSerialNumber, from that certificate object. This is not supported in an update dictionary. For kSecValuePersistentRef: For query dictionaries, this uniquely identifies the item to operate on. This is not supported in add and update dictionaries. Revision History 2025-05-28 Expanded the Caveat Mac Developer section to cover some subtleties associated with the deprecation of the file-based keychain. 2023-09-12 Fixed various bugs in the revision history. Added a paragraph explaining how to determine which attributes are supported by each keychain item class. 2023-02-22 Made minor editorial changes. 2023-01-28 First posted.
Replies
0
Boosts
0
Views
4.4k
Activity
May ’25
TLS for App Developers
Transport Layer Security (TLS) is the most important security protocol on the Internet today. Most notably, TLS puts the S into HTTPS, adding security to the otherwise insecure HTTP protocol. IMPORTANT TLS is the successor to the Secure Sockets Layer (SSL) protocol. SSL is no longer considered secure and it’s now rarely used in practice, although many folks still say SSL when they mean TLS. TLS is a complex protocol. Much of that complexity is hidden from app developers but there are places where it’s important to understand specific details of the protocol in order to meet your requirements. This post explains the fundamentals of TLS, concentrating on the issues that most often confuse app developers. Note The focus of this is TLS-PKI, where PKI stands for public key infrastructure. This is the standard TLS as deployed on the wider Internet. There’s another flavour of TLS, TLS-PSK, where PSK stands for pre-shared key. This has a variety of uses, but an Apple platforms we most commonly see it with local traffic, for example, to talk to a Wi-Fi based accessory. For more on how to use TLS, both TLS-PKI and TLS-PSK, in a local context, see TLS For Accessory Developers. Server Certificates For standard TLS to work the server must have a digital identity, that is, the combination of a certificate and the private key matching the public key embedded in that certificate. TLS Crypto Magic™ ensures that: The client gets a copy of the server’s certificate. The client knows that the server holds the private key matching the public key in that certificate. In a typical TLS handshake the server passes the client a list of certificates, where item 0 is the server’s certificate (the leaf certificate), item N is (optionally) the certificate of the certificate authority that ultimately issued that certificate (the root certificate), and items 1 through N-1 are any intermediate certificates required to build a cryptographic chain of trust from 0 to N. Note The cryptographic chain of trust is established by means of digital signatures. Certificate X in the chain is issued by certificate X+1. The owner of certificate X+1 uses their private key to digitally sign certificate X. The client verifies this signature using the public key embedded in certificate X+1. Eventually this chain terminates in a trusted anchor, that is, a certificate that the client trusts by default. Typically this anchor is a self-signed root certificate from a certificate authority. Note Item N is optional for reasons I’ll explain below. Also, the list of intermediate certificates may be empty (in the case where the root certificate directly issued the leaf certificate) but that’s uncommon for servers in the real world. Once the client gets the server’s certificate, it evaluates trust on that certificate to confirm that it’s talking to the right server. There are three levels of trust evaluation here: Basic X.509 trust evaluation checks that there’s a cryptographic chain of trust from the leaf through the intermediates to a trusted root certificate. The client has a set of trusted root certificates built in (these are from well-known certificate authorities, or CAs), and a site admin can add more via a configuration profile. This step also checks that none of the certificates have expired, and various other more technical criteria (like the Basic Constraints extension). Note This explains why the server does not have to include the root certificate in the list of certificates it passes to the client; the client has to have the root certificate installed if trust evaluation is to succeed. In addition, TLS trust evaluation (per RFC 2818) checks that the DNS name that you connected to matches the DNS name in the certificate. Specifically, the DNS name must be listed in the Subject Alternative Name extension. Note The Subject Alternative Name extension can also contain IP addresses, although that’s a much less well-trodden path. Also, historically it was common to accept DNS names in the Common Name element of the Subject but that is no longer the case on Apple platforms. App Transport Security (ATS) adds its own security checks. Basic X.509 and TLS trust evaluation are done for all TLS connections. ATS is only done on TLS connections made by URLSession and things layered on top URLSession (like WKWebView). In many situations you can override trust evaluation; for details, see Technote 2232 HTTPS Server Trust Evaluation). Such overrides can either tighten or loosen security. For example: You might tighten security by checking that the server certificate was issued by a specific CA. That way, if someone manages to convince a poorly-managed CA to issue them a certificate for your server, you can detect that and fail. You might loosen security by adding your own CA’s root certificate as a trusted anchor. IMPORTANT If you rely on loosened security you have to disable ATS. If you leave ATS enabled, it requires that the default server trust evaluation succeeds regardless of any customisations you do. Mutual TLS The previous section discusses server trust evaluation, which is required for all standard TLS connections. That process describes how the client decides whether to trust the server. Mutual TLS (mTLS) is the opposite of that, that is, it’s the process by which the server decides whether to trust the client. Note mTLS is commonly called client certificate authentication. I avoid that term because of the ongoing industry-wide confusion between certificates and digital identities. While it’s true that, in mTLS, the server authenticates the client certificate, to set this up on the client you need a digital identity, not a certificate. mTLS authentication is optional. The server must request a certificate from the client and the client may choose to supply one or not (although if the server requests a certificate and the client doesn’t supply one it’s likely that the server will then fail the connection). At the TLS protocol level this works much like it does with the server certificate. For the client to provide this certificate it must apply a digital identity, known as the client identity, to the connection. TLS Crypto Magic™ assures the server that, if it gets a certificate from the client, the client holds the private key associated with that certificate. Where things diverge is in trust evaluation. Trust evaluation of the client certificate is done on the server, and the server uses its own rules to decided whether to trust a specific client certificate. For example: Some servers do basic X.509 trust evaluation and then check that the chain of trust leads to one specific root certificate; that is, a client is trusted if it holds a digital identity whose certificate was issued by a specific CA. Some servers just check the certificate against a list of known trusted client certificates. When the client sends its certificate to the server it actually sends a list of certificates, much as I’ve described above for the server’s certificates. In many cases the client only needs to send item 0, that is, its leaf certificate. That’s because: The server already has the intermediate certificates required to build a chain of trust from that leaf to its root. There’s no point sending the root, as I discussed above in the context of server trust evaluation. However, there are no hard and fast rules here; the server does its client trust evaluation using its own internal logic, and it’s possible that this logic might require the client to present intermediates, or indeed present the root certificate even though it’s typically redundant. If you have problems with this, you’ll have to ask the folks running the server to explain its requirements. Note If you need to send additional certificates to the server, pass them to the certificates parameter of the method you use to create your URLCredential (typically init(identity:certificates:persistence:)). One thing that bears repeating is that trust evaluation of the client certificate is done on the server, not the client. The client doesn’t care whether the client certificate is trusted or not. Rather, it simply passes that certificate the server and it’s up to the server to make that decision. When a server requests a certificate from the client, it may supply a list of acceptable certificate authorities [1]. Safari uses this to filter the list of client identities it presents to the user. If you are building an HTTPS server and find that Safari doesn’t show the expected client identity, make sure you have this configured correctly. If you’re building an iOS app and want to implement a filter like Safari’s, get this list using: The distinguishedNames property, if you’re using URLSession The sec_protocol_metadata_access_distinguished_names routine, if you’re using Network framework [1] See the certificate_authorities field in Section 7.4.4 of RFC 5246, and equivalent features in other TLS versions. Self-Signed Certificates Self-signed certificates are an ongoing source of problems with TLS. There’s only one unequivocally correct place to use a self-signed certificate: the trusted anchor provided by a certificate authority. One place where a self-signed certificate might make sense is in a local environment, that is, securing a connection between peers without any centralised infrastructure. However, depending on the specific circumstances there may be a better option. TLS For Accessory Developers discusses this topic in detail. Finally, it’s common for folks to use self-signed certificates for testing. I’m not a fan of that approach. Rather, I recommend the approach described in QA1948 HTTPS and Test Servers. For advice on how to set that up using just your Mac, see TN2326 Creating Certificates for TLS Testing. TLS Standards RFC 6101 The Secure Sockets Layer (SSL) Protocol Version 3.0 (historic) RFC 2246 The TLS Protocol Version 1.0 RFC 4346 The Transport Layer Security (TLS) Protocol Version 1.1 RFC 5246 The Transport Layer Security (TLS) Protocol Version 1.2 RFC 8446 The Transport Layer Security (TLS) Protocol Version 1.3 RFC 4347 Datagram Transport Layer Security RFC 6347 Datagram Transport Layer Security Version 1.2 RFC 9147 The Datagram Transport Layer Security (DTLS) Protocol Version 1.3 Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" Revision History: 2025-11-21 Clearly defined the terms TLS-PKI and TLS-PSK. 2024-03-19 Adopted the term mutual TLS in preference to client certificate authentication throughout, because the latter feeds into the ongoing certificate versus digital identity confusion. Defined the term client identity. Added the Self-Signed Certificates section. Made other minor editorial changes. 2023-02-28 Added an explanation mTLS acceptable certificate authorities. 2022-12-02 Added links to the DTLS RFCs. 2022-08-24 Added links to the TLS RFCs. Made other minor editorial changes. 2022-06-03 Added a link to TLS For Accessory Developers. 2021-02-26 Fixed the formatting. Clarified that ATS only applies to URLSession. Minor editorial changes. 2020-04-17 Updated the discussion of Subject Alternative Name to account for changes in the 2019 OS releases. Minor editorial updates. 2018-10-29 Minor editorial updates. 2016-11-11 First posted.
Replies
0
Boosts
0
Views
8.3k
Activity
Nov ’25
Mark the iOS app content not to be backed up when doing unencrypted backup in iTunes
Hi,is there an option to mark the file or folder or item stored in user defaults ... not to be backed up when doing unencrypted backup in iTunes?We are developing iOS app that contains sensitive data. But even if we enable Data Protection for the iOS app it can be backed up on mac unencrypted using iTunes. Is there a way to allow backing up content only if the backup is encrypted?
Replies
2
Boosts
0
Views
1.8k
Activity
Oct ’25
security add-trusted-cert asks password twice in some cases: The authorization was denied since no user interaction was possible
Hey devs, I have a really weird issue and at this point I cannot determine is it a Big Sur 11.1 or M1 issue or just some macOS settings issue. Short description programatically (from node, electron) I'd like to store x509 cert to keychain. I got the following error message: SecTrustSettingsSetTrustSettings: The authorization was denied since no user interaction was possible. (1) I could reproduce this issue on: a brand new mac mini with M1 chip and Big Sur 11.1 another brand new mac mini with M1 chip and Big Sur 11.1 a 2018 MacBook pro with Intel chip and Big Sur 11.1 I couldn't reproduce this issue on: 2020 MacBook pro with intel i9 chip and Big Sur 11.1 2020 MacBook pro with intel i9 chip and Big Sur 11.0 How am I trying to store the cert node test.js test.js const { exec } = require('child_process') exec( &#9;`osascript -e 'do shell script "security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /Users/kotapeter/ssl/testsite.local.crt" with prompt "Test APP wants to store SSL certification to keychain." with administrator privileges'`, &#9;(error, stdout, stderr) => { &#9;&#9;if (error) { &#9;&#9;&#9;console.log(error.stack) &#9;&#9;&#9;console.log(`Error code: ${error.code}`) &#9;&#9;&#9;console.log(`Signal received: ${error.signal}`) &#9;&#9;} &#9;&#9;console.log(`STDOUT: ${stdout}`) &#9;&#9;console.log(`STDERR: ${stderr}`) &#9;&#9;process.exit(1) &#9;} ) testsite.local.crt: ----BEGIN CERTIFICATE MIIDUzCCAjugAwIBAgIUD9xMnL73y7fuida5TXgmklLswsowDQYJKoZIhvcNAQEL BQAwGTEXMBUGA1UEAwwOdGVzdHNpdGUubG9jYWwwHhcNMjEwMTE3MTExODU1WhcN NDEwMTEyMTExODU1WjAZMRcwFQYDVQQDDA50ZXN0c2l0ZS5sb2NhbDCCASIwDQYJ KoZIhvcNAQEBBQADggEPADCCAQoCggEBANM08SDi06dvnyU1A6//BeEFd8mXsOpD QCbYEHX/Pz4jqaBYwVjD5pG7FkvDeUKZnEVyrsofjZ4Y1WAT8jxPMUi+jDlgNTiF jPVc4rA6hcGX6b70HjsCACmc8bZd+EU7gm4b5eL6exTsVzHc+lFz4eQFXgutYTL7 guDQE/gFHwqPkLvnfg3rgY31p3Hm/snL8NuD154iE9O1WuSxEjik65uOQaewZmJ9 ejJEuuEhMA8O9dXveJ71TMV5lqA//svDxBu3zXIxMqRy2LdzfROd+guLP6ZD3jUy cWi7GpF4yN0+rD/0aXFJVHzV6TpS9oqb14jynvn1AyVfBB9+VQVNwTsCAwEAAaOB kjCBjzAJBgNVHRMEAjAAMAsGA1UdDwQEAwIC9DA7BgNVHSUENDAyBggrBgEFBQcD AQYIKwYBBQUHAwIGCCsGAQUFBwMDBggrBgEFBQcDBAYIKwYBBQUHAwgwHQYDVR0O BBYEFDjAC2ObSbB59XyLW1YaD7bgY8ddMBkGA1UdEQQSMBCCDnRlc3RzaXRlLmxv Y2FsMA0GCSqGSIb3DQEBCwUAA4IBAQBsU6OA4LrXQIZDXSIZPsDhtA7YZWzbrpqP ceXPwBd1k9Yd9T83EdA00N6eoOWFzwnQqwqKxtYdl3x9JQ7ewhY2huH9DRtCGjiT m/GVU/WnNm4tUTuGU4FyjSTRi8bNUxTSF5PZ0U2/vFZ0d7T43NbLQAiFSxyfC1r6 qjKQCYDL92XeU61zJxesxy5hxVNrbDpbPnCUZpx4hhL0RHgG+tZBOlBuW4eq249O 0Ql+3ShcPom4hzfh975385bfwfUT2s/ovng67IuM9bLSWWe7U+6HbOEvzMIiqK94 YYPmOC62cdhOaZIJmro6lL7eFLqlYfLU4H52ICuntBxvOx0UBExn----END CERTIFICATE testsite.local.key: ----BEGIN RSA PRIVATE KEY MIIEpQIBAAKCAQEA0zTxIOLTp2+fJTUDr/8F4QV3yZew6kNAJtgQdf8/PiOpoFjB WMPmkbsWS8N5QpmcRXKuyh+NnhjVYBPyPE8xSL6MOWA1OIWM9VzisDqFwZfpvvQe OwIAKZzxtl34RTuCbhvl4vp7FOxXMdz6UXPh5AVeC61hMvuC4NAT+AUfCo+Qu+d+ DeuBjfWnceb+ycvw24PXniIT07Va5LESOKTrm45Bp7BmYn16MkS64SEwDw711e94 nvVMxXmWoD/+y8PEG7fNcjEypHLYt3N9E536C4s/pkPeNTJxaLsakXjI3T6sP/Rp cUlUfNXpOlL2ipvXiPKe+fUDJV8EH35VBU3BOwIDAQABAoIBAQDDGLJsiFqu3gMK IZCIcHCDzcM7Kq43l2uY9hkuhltrERJNle70CfHgSAtubOCETtT1qdwfxUnR8mqX 15T5dMW3xpxNG7vNvD/bHrQfyc9oZuV6iJGsPEreJaV5qg/+E9yFzatrIam0SCS7 YL6xovPU58hZzQxuRbo95LetcT2dSBY33+ttY7ayV/Lx7k6nh0xU6RmTPHyyr8m7 yHpoJoSxdT/xv5iBSZ8mM9/2Vzhr14SWipVuwVVhDSfbn8ngHpIoQDkaJLMpWr+m 4z3PqfftAwR6s6i96HnhYLnRir618TQh4B9IEngeEwCMn4XAzE3L+VTaKU1hg9el aMfXzPERAoGBAPa+sJ2p9eQsv0vCUUL8KeRWvwjDZRTd+YAIfpLMWrb0tMmrBM4V V0L2joF76kdDxt1SAlHoYCT/3Rn8EPmK0TN3MEskiXQ7v57iv+LZOZcpe0ppG/4A ZihF9+wUjFCDw4ymnRQD463535O6BgZV+rcZksFRD2AwvEjt1nYm93VXAoGBANsh AYM+FPmMnzebUMB0oGIkNkE9nVb9MPbQYZjEeOeHJqmt1Nl6xLuYBWTmWwCy7J4e QPtnuMCdO6C1kuOGjQPBFIpeyFMzll+E3hKzicumgCpt5U8nTZoKc/jZckRD7n3p lbYYgHOR3A/3GCDK5L3rwziWpSRAGMSCQylvkOC9AoGBAKLfZL3t/r3LO8rKTdGl mhF7oUYrlIGdtJ/q+4HzGr5B8URdeyJ9u8gb8B1Qqmi4OIDHLXjbpvtFWbFZTesq 0sTiHCK9z23GMsqyam9XbEh3vUZ082FK6iQTa3+OYMCU+XPSV0Vq+9NPaWGeHXP5 NTG/07t/wmKASQjq1fHP7vCpAoGBAK4254T4bqSYcF09Vk4savab46aq3dSzJ6KS uYVDbvxkLxDn6zmcqZybmG5H1kIP/p8XXoKCTBiW6Tk0IrxR1PsPHs2D3bCIax01 /XjQ1NTcYzlYdd8gWEoH1XwbJQWxHINummBTyowXguYOhVhM9t8n+eWbn1/atdZF 2i+vS3fhAoGAYKw6rkJfTSEswgBKlQFJImxVA+bgKsEwUti1aBaIA2vyIYWDeV10 G8hlUDlxvVkfwCJoy5zz6joGGO/REhqOkMbFRPseA50u2NQVuK5C+avUXdcILJHN zp0nC5eZpP1TC++uCboJxo5TIdbLL7GRwQfffgALRBpK12Vijs195cc=----END RSA PRIVATE KEY What I've already found If I run the following command from terminal It asks my password first in terminal and after that It asks my password again in OS password prompt. sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /Users/kotapeter/ssl/testsite.local.crt It looks like I'm getting the above error message because osascript hides the second password asking dialog. The cert always gets stored in keychain but when I get the error message the cert "Trust" value is not "Always Trust". References StackOverflow question: https://stackoverflow.com/questions/65699160/electron-import-x509-cert-to-local-keychain-macos-the-authorization-was-deni opened issue on sudo-prompt electron package: https://github.com/jorangreef/sudo-prompt/issues/137
Replies
14
Boosts
0
Views
20k
Activity
Oct ’25
App ID Prefix Change and Keychain Access
DTS regularly receives questions about how to preserve keychain items across an App ID change, and so I thought I’d post a comprehensive answer here for the benefit of all. If you have any questions or comments, please start a new thread here on the forums. Put it in the Privacy & Security > General subtopic and tag it with Security. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" App ID Prefix Change and Keychain Access The list of keychain access groups your app can access is determined by three entitlements. For the details, see Sharing Access to Keychain Items Among a Collection of Apps. If your app changes its App ID prefix, this list changes and you’re likely to lose access to existing keychain items. This situation crops up under two circumstances: When you migrate your app from using a unique App ID prefix to using your Team ID as its App ID prefix. When you transfer your app to another team. In both cases you have to plan carefully for this change. If you only learn about the problem after you’ve made the change, consider undoing the change to give you time to come up with a plan before continuing. Note On macOS, the information in this post only applies to the data protection keychain. For more information about the subtleties of the keychain on macOS, see On Mac Keychains. For more about App ID prefix changes, see Technote 2311 Managing Multiple App ID Prefixes and QA1726 Resolving the Potential Loss of Keychain Access warning. Migrate From a Unique App ID Prefix to Your Team ID Historically each app was assigned its own App ID prefix. This is no longer the case. Best practice is for apps to use their Team ID as their App ID prefix. This enables multiple neat features, including keychain item sharing and pasteboard sharing. If you have an app that uses a unique App ID prefix, consider migrating it to use your Team ID. This is a good thing in general, as long as you manage the migration process carefully. Your app’s keychain access group list is built from three entitlements: keychain-access-groups — For more on this, see Keychain Access Groups Entitlement. application-identifier (com.apple.application-identifier on macOS) com.apple.security.application-groups — For more on this, see App Groups Entitlement. Keycahin access groups from the third bullet are call app group identified keychain access groups, or AGI keychain access groups for short. IMPORTANT A macOS app can only use an AGI keychain access group if all of its entitlement claims are validated by a provisioning profile. See App Groups: macOS vs iOS: Working Towards Harmony for more about this concept. Keychain access groups from the first two bullets depend on the App ID prefix. If that changes, you lose access to any keychain items in those groups. WARNING Think carefully before using the keychain to store secrets that are the only way to access irreplaceable user data. While the keychain is very reliable, there are situations where a keychain item can be lost and it’s bad if it takes the user’s data with it. In some cases losing access to keychain items is not a big deal. For example, if your app uses the keychain to manage a single login credential, losing that is likely to be acceptable. The user can recover by logging in again. In other cases losing access to keychain items is unacceptable. For example, your app might manage access to dozens of different servers, each with unique login credentials. Your users will be grumpy if you require them to log in to all those servers again. In such situations you must carefully plan your migration. The key thing to understand is that an app group is tied to your team, not your App ID prefix, and thus your app retains access to AGI keychain access groups across an App ID prefix change. This suggests the following approach: Release a version of your app that moves keychain items from other keychain access groups to an AGI keychain access group. Give your users time to update to this new version, run it, and so move their keychain items. When you’re confident that the bulk of your users have done this, change your App ID prefix. The approach has one obvious caveat: It’s hard to judge how long to wait at step 2. Transfer Your App to Another Team Historically there was no supported way to maintain access to keychain items across an app transfer. That’s no longer the case, but you must still plan the transfer carefully. The overall approach is: Identify an app group ID to transfer. This could be an existing app group ID, but in many cases you’ll want to register a new app group ID solely for this purpose. Use the old team (the transferor) to release a version of your app that moves keychain items from other keychain access groups to the AGI keychain access group for this app group ID. Give your users time to update to this new version, run it, and so move their keychain items. When you’re confident that the bulk of your users have done this, initiate the app transfer. Once that’s complete, transfer the app group ID you selected in step 1. See App Store Connect Help > Transfer an app > Overview of app transfer > Apps using App Groups. Publish an update to your app from the new team (the transferee). When a user installs this version, it will have access to your app group, and hence your keychain items. WARNING Once you transfer the app group, the old team won’t be able to publish a new version of any app that uses this app group. That makes step 1 in the process critical. If you have an existing app group that’s used solely by the app being transferred — for example, an app group that you use to share state between the app and its app extensions — then choosing that app group ID makes sense. On the other hand, choosing the ID of an app group that’s share between this app and some unrelated app, one that’s not being transferred, would be bad, because any updates to that other app will lose access to the app group. There are some other significant caveats: The process doesn’t work for Mac apps because Mac apps that have ever used an app group can’t be transferred. See App Store Connect Help > Transfer an app > App transfer criteria. If and when that changes, you’ll need to choose an iOS-style app group ID for your AGI keychain access group. For more about the difference between iOS- and macOS-style app group IDs, see App Groups: macOS vs iOS: Working Towards Harmony. The current transfer process of app groups exposes a small window where some other team can ‘steal’ your app group ID. We have a bug on file to improve that process (r. 171616887). The process works best when transferring between two teams that are both under the control of the same entity. If that’s not the case, take steps to ensure that the old team transfers the app group in step 5. When you submit the app from the new team (step 6), App Store Connect will warn you about a potential loss of keychain access. That warning is talking about keychain items in normal keychain access groups. Items in an AGI keychain access group will still be accessible as long as you transfer the app group. Alternative Approaches for App Transfer In addition to the technique described in the previous section, there are a some alternative approaches you should at consider: Do nothing Do not transfer your app Get creative Do Nothing In this case the user loses all the secrets that your app stored in the keychain. This may be acceptable for certain apps. For example, if your app uses the keychain to manage a single login credential, losing that is likely to be acceptable. The user can recover by logging in again. Do Not Transfer Another option is to not transfer your app. Instead, ship a new version of the app from the new team and have the old app recommend that the user upgrade. There are a number of advantages to this approach. The first is that there’s absolutely no risk of losing any user data. The two apps are completely independent. The second advantage is that the user can install both apps on their device at the same time. This opens up a variety of potential migration paths. For example, you might ship an update to the old app with an export feature that saves the user’s state, including their secrets, to a suitably encrypted file, and then match that with an import facility on the new app. Finally, this approach offers flexible timing. The user can complete their migration at their leisure. However, there are a bunch of clouds to go with these silver linings: Your users might never migrate to the new app. If this is a paid app, or an app with in-app purchase, the user will have to buy things again. You lose the original app’s history, ratings, reviews, and so on. Get Creative Finally, you could attempt something creative. For example, you might: Publish a new version of the app that supports exporting the user’s state, including the secrets. Tell your users to do this, with a deadline. Transfer the app and then, when the deadline expires, publish the new version with an import feature. Frankly, this isn’t very practical. The problem is with step 2: There’s no good way to get all your users to do the export, and if they don’t do it before the deadline there’s no way to do it after. Revision History 2026-03-31 Rewrote the Transfer Your App to Another Team section to describe a new approach for preserving access to keychain items across app transfers. Moved the previous discussion into a new Alternative Approaches for App Transfer section. Clarified that a macOS program can now use an app group as a keychain access group as long as its entitlements are validated. Made numerous editorial changes. 2022-05-17 First posted.
Replies
0
Boosts
0
Views
8.5k
Activity
1d
Security Resources
General: Forums topic: Privacy & Security Apple Platform Security support document Developer > Security Enabling enhanced security for your app documentation article Creating enhanced security helper extensions documentation article Security Audit Thoughts forums post Cryptography: Forums tags: Security, Apple CryptoKit Security framework documentation Apple CryptoKit framework documentation Common Crypto man pages — For the full list of pages, run: % man -k 3cc For more information about man pages, see Reading UNIX Manual Pages. On Cryptographic Key Formats forums post SecItem attributes for keys forums post CryptoCompatibility sample code Keychain: Forums tags: Security Security > Keychain Items documentation TN3137 On Mac keychain APIs and implementations SecItem Fundamentals forums post SecItem Pitfalls and Best Practices forums post Investigating hard-to-reproduce keychain problems forums post App ID Prefix Change and Keychain Access forums post Smart cards and other secure tokens: Forums tag: CryptoTokenKit CryptoTokenKit framework documentation Mac-specific resources: Forums tags: Security Foundation, Security Interface Security Foundation framework documentation Security Interface framework documentation BSD Privilege Escalation on macOS Related: Networking Resources — This covers high-level network security, including HTTPS and TLS. Network Extension Resources — This covers low-level network security, including VPN and content filters. Code Signing Resources Notarisation Resources Trusted Execution Resources — This includes Gatekeeper. App Sandbox Resources Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com"
Replies
0
Boosts
0
Views
3.8k
Activity
Nov ’25
Is there any public API apple provides to detect Lockdown Mode in iOS 16?
Hi, I was testing the lockdown mode in iOS 16 and would like to know whether we can detect the lockdown mode status using any public API that Apple provides. I really appreciate any help you can provide.
Replies
8
Boosts
0
Views
2.8k
Activity
Jun ’25
SecItem: Pitfalls and Best Practices
I regularly help developers with keychain problems, both here on DevForums and for my Day Job™ in DTS. Over the years I’ve learnt a lot about the API, including many pitfalls and best practices. This post is my attempt to collect that experience in one place. If you have questions or comments about any of this, put them in a new thread and apply the Security tag so that I see it. Share and Enjoy — Quinn “The Eskimo!” @ Developer Technical Support @ Apple let myEmail = "eskimo" + "1" + "@" + "apple.com" SecItem: Pitfalls and Best Practices It’s just four functions, how hard can it be? The SecItem API seems very simple. After all, it only has four function calls, how hard can it be? In reality, things are not that easy. Various factors contribute to making this API much trickier than it might seem at first glance. This post explains some of the keychain’s pitfalls and then goes on to explain various best practices. Before reading this, make sure you understand the fundamentals by reading its companion post, SecItem: Fundamentals. Pitfalls Lets start with some common pitfalls. Queries and Uniqueness Constraints The relationship between query dictionaries and uniqueness constraints is a major source of problems with the keychain API. Consider code like this: var copyResult: CFTypeRef? = nil let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecAttrGeneric: Data("SecItemHints".utf8), ] as NSMutableDictionary let err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { query[kSecValueData] = Data("opendoor".utf8) let err2 = SecItemAdd(query, nil) if err2 == errSecDuplicateItem { fatalError("… can you get here? …") } } Can you get to the fatal error? At first glance this might not seem possible because you’ve run your query and it’s returned errSecItemNotFound. However, the fatal error is possible because the query contains an attribute, kSecAttrGeneric, that does not contribute to the uniqueness. If the keychain contains a generic password whose service (kSecAttrService) and account (kSecAttrAccount) attributes match those supplied but whose generic (kSecAttrGeneric) attribute does not, the SecItemCopyMatching calls will return errSecItemNotFound. However, for a generic password item, of the attributes shown here, only the service and account attributes are included in the uniqueness constraint. If you try to add an item where those attributes match an existing item, the add will fail with errSecDuplicateItem even though the value of the generic attribute is different. The take-home point is that that you should study the attributes that contribute to uniqueness and use them in a way that’s aligned with your view of uniqueness. See the Uniqueness section of SecItem: Fundamentals for a link to the relevant documentation. Erroneous Attributes Each keychain item class supports its own specific set of attributes. For information about the attributes supported by a given class, see SecItem: Fundamentals. I regularly see folks use attributes that aren’t supported by the class they’re working with. For example, the kSecAttrApplicationTag attribute is only supported for key items (kSecClassKey). Using it with a certificate item (kSecClassCertificate) will cause, at best, a runtime error and, at worst, mysterious bugs. This is an easy mistake to make because: The ‘parameter block’ nature of the SecItem API means that the compiler won’t complain if you use an erroneous attribute. On macOS, the shim that connects to the file-based keychain ignores unsupported attributes. Imagine you want to store a certificate for a particular user. You might write code like this: let err = SecItemAdd([ kSecClass: kSecClassCertificate, kSecAttrApplicationTag: Data(name.utf8), kSecValueRef: cert, ] as NSDictionary, nil) The goal is to store the user’s name in the kSecAttrApplicationTag attribute so that you can get back their certificate with code like this: let err = SecItemCopyMatching([ kSecClass: kSecClassCertificate, kSecAttrApplicationTag: Data(name.utf8), kSecReturnRef: true, ] as NSDictionary, &copyResult) On iOS, and with the data protection keychain on macOS, both calls will fail with errSecNoSuchAttr. That makes sense, because the kSecAttrApplicationTag attribute is not supported for certificate items. Unfortunately, the macOS shim that connects the SecItem API to the file-based keychain ignores extraneous attributes. This results in some very bad behaviour: SecItemAdd works, ignoring kSecAttrApplicationTag. SecItemCopyMatching ignores kSecAttrApplicationTag, returning the first certificate that it finds. If you only test with a single user, everything seems to work. But, later on, when you try your code with multiple users, you might get back the wrong result depending on the which certificate the SecItemCopyMatching call happens to discover first. Ouch! Context Matters Some properties change behaviour based on the context. The value type properties are the biggest offender here, as discussed in the Value Type Subtleties section of SecItem: Fundamentals. However, there are others. The one that’s bitten me is kSecMatchLimit: In a query and return dictionary its default value is kSecMatchLimitOne. If you don’t supply a value for kSecMatchLimit, SecItemCopyMatching returns at most one item that matches your query. In a pure query dictionary its default value is kSecMatchLimitAll. For example, if you don’t supply a value for kSecMatchLimit, SecItemDelete will delete all items that match your query. This is a lesson that, once learnt, is never forgotten! Note Although this only applies to the data protection keychain. If you’re on macOS and targeting the file-based keychain, kSecMatchLimit always defaults to kSecMatchLimitOne (r. 105800863). Fun times! Digital Identities Aren’t Real A digital identity is the combination of a certificate and the private key that matches the public key within that certificate. The SecItem API has a digital identity keychain item class, namely kSecClassIdentity. However, the keychain does not store digital identities. When you add a digital identity to the keychain, the system stores its components, the certificate and the private key, separately, using kSecClassCertificate and kSecClassKey respectively. This has a number of non-obvious effects: Adding a certificate can ‘add’ a digital identity. If the new certificate happens to match a private key that’s already in the keychain, the keychain treats that pair as a digital identity. Likewise when you add a private key. Similarly, removing a certificate or private key can ‘remove’ a digital identity. Adding a digital identity will either add a private key, or a certificate, or both, depending on what’s already in the keychain. Removing a digital identity removes its certificate. It might also remove the private key, depending on whether that private key is used by a different digital identity. The system forms a digital identity by matching the kSecAttrApplicationLabel (klbl) attribute of the private key with the kSecAttrPublicKeyHash (pkhh) attribute of the certificate. If you add both items to the keychain and the system doesn’t form an identity, check the value of these attributes. For more information the key attributes, see SecItem attributes for keys. Keys Aren’t Stored in the Secure Enclave Apple platforms let you protect a key with the Secure Enclave (SE). The key is then hardware bound. It can only be used by that specific SE [1]. Earlier versions of the Protecting keys with the Secure Enclave article implied that SE-protected keys were stored in the SE itself. This is not true, and it’s caused a lot of confusion. For example, I once asked the keychain team “How much space does the SE have available to store keys?”, a question that’s complete nonsense once you understand how this works. In reality, SE-protected keys are stored in the standard keychain database alongside all your other keychain items. The difference is that the key is wrapped in such a way that only the SE can use it. So, the key is protected by the SE, not stored in the SE. A while back we updated the docs to clarify this point but the confusion persists. [1] Technically it’s that specific iteration of that specific SE. If you erase the device then the key material needed to use the key is erased and so the key becomes permanently useless. This is the sort of thing you’ll find explained in Apple Platform Security. Careful With that Shim, Mac Developer As explained in TN3137 On Mac keychain APIs and implementations, macOS has a shim that connects the SecItem API to either the data protection keychain or the file-based keychain depending on the nature of the request. That shim has limitations. Some of those are architectural but others are simply bugs in the shim. For some great examples, see the Investigating Complex Attributes section below. The best way to avoid problems like this is to target the data protection keychain. If you can’t do that, try to avoid exploring the outer reaches of the SecItem API. If you encounter a case that doesn’t make sense, try that same case with the data protection keychain. If it works there but fails with the file-based keychain, please do file a bug against the shim. It’ll be in good company. Here’s some known issues with the shim: It ignores unsupported attributes. See Erroneous Attributes, above, for more background on that. The shim can fan out to both the data protection and the file-based keychain. In that case it has to make a policy decision about how to handle errors. This results in some unexpected behaviour (r. 143405965). For example, if you call SecItemCopyMatching while the keychain is locked, the data protection keychain will fail with errSecInteractionNotAllowed (-25308). OTOH, it’s possible to query for the presence of items in the file-based keychain even when it’s locked. If you do that and there’s no matching item, the file-based keychain fails with errSecItemNotFound (-25300). When the shim gets these conflicting errors, it chooses to return the latter. Whether this is right or wrong depends on your perspective, but it’s certainly confusing, especially if you’re coming at this from the iOS side. If you call SecItemDelete without specifying a match limit (kSecMatchLimit), the data protection keychain deletes all matching items, whereas the file-based keychain just deletes a single match (r. 105800863). While these issue have all have bug numbers, there’s no guarantee that any of them will be fixed. Fixing bugs like this is tricky because of binary compatibility concerns. Add-only Attributes Some attributes can only be set when you add an item. These attributes are usually associated with the scope of the item. For example, to protect an item with the Secure Enclave, supply the kSecAttrAccessControl attribute to the SecItemAdd call. Once you do that, however, you can’t change the attribute. Calling SecItemUpdate with a new kSecAttrAccessControl won’t work. Lost Keychain Items A common complaint from developers is that a seemingly minor update to their app has caused it to lose all of its keychain items. Usually this is caused by one of two problems: Entitlement changes Query dictionary confusion Access to keychain items is mediated by various entitlements, as described in Sharing access to keychain items among a collection of apps. If the two versions of your app have different entitlements, one version may not be able to ‘see’ items created by the other. Imagine you have an app with an App ID of SKMME9E2Y8.com.example.waffle-varnisher. Version 1 of your app is signed with the keychain-access-groups entitlement set to [ SKMME9E2Y8.groupA, SKMME9E2Y8.groupB ]. That makes its keychain access group list [ SKMME9E2Y8.groupA, SKMME9E2Y8.groupB, SKMME9E2Y8.com.example.waffle-varnisher ]. If this app creates a new keychain item without specifying kSecAttrAccessGroup, the system places the item into SKMME9E2Y8.groupA. If version 2 of your app removes SKMME9E2Y8.groupA from the keychain-access-groups, it’ll no longer be able to see the keychain items created by version 1. You’ll also see this problem if you change your App ID prefix, as described in App ID Prefix Change and Keychain Access. IMPORTANT When checking for this problem, don’t rely on your .entitlements file. There are many steps between it and your app’s actual entitlements. Rather, run codesign to dump the entitlements of your built app: % codesign -d --entitlements - /path/to/your.app Lost Keychain Items, Redux Another common cause of lost keychain items is confusion about query dictionaries, something discussed in detail in this post and SecItem: Fundamentals. If SecItemCopyMatching isn’t returning the expected item, add some test code to get all the items and their attributes. For example, to dump all the generic password items, run code like this: func dumpGenericPasswords() throws { let itemDicts = try secCall { SecItemCopyMatching([ kSecClass: kSecClassGenericPassword, kSecMatchLimit: kSecMatchLimitAll, kSecReturnAttributes: true, ] as NSDictionary, $0) } as! [[String: Any]] print(itemDicts) } Then compare each item’s attributes against the attributes you’re looking for to see why there was no match. Data Protection and Background Execution Keychain items are subject to data protection. Specifically, an item may or may not be accessible depending on whether specific key material is available. For an in-depth discussion of how this works, see Apple Platform Security. Note This section focuses on iOS but you’ll see similar effects on all Apple platforms. On macOS specifically, the contents of this section only apply to the data protection keychain. The keychain supports three data protection levels: kSecAttrAccessibleWhenUnlocked kSecAttrAccessibleAfterFirstUnlock kSecAttrAccessibleAlways Note There are additional data protection levels, all with the ThisDeviceOnly suffix. Understanding those is not necessary to understanding this pitfall. Each data protection level describes the lifetime of the key material needed to work with items protected in that way. Specifically: The key material needed to work with a kSecAttrAccessibleWhenUnlocked item comes and goes as the user locks and unlocks their device. The key material needed to work with a kSecAttrAccessibleAfterFirstUnlock item becomes available when the device is first unlocked and remains available until the device restarts. The default data protection level is kSecAttrAccessibleWhenUnlocked. If you add an item to the keychain and don’t specify a data protection level, this is what you get [1]. To specify a data protection level when you add an item to the keychain, apply the kSecAttrAccessible attribute. Alternatively, embed the access level within a SecAccessControl object and apply that using the kSecAttrAccessControl attribute. IMPORTANT It’s best practice to set these attributes when you add the item and then never update them. See Add-only Attributes, above, for more on that. If you perform an operation whose data protection is incompatible with the currently available key material, that operation fails with errSecInteractionNotAllowed [2]. There are four fundamental keychain operations, discussed in the SecItem: Fundamentals, and each interacts with data protection in a different way: Copy — If you attempt to access a keychain item whose key material is unavailable, SecItemCopyMatching fails with errSecInteractionNotAllowed. This is an obvious result; the whole point of data protection is to enforce this security policy. Add — If you attempt to add a keychain item whose key material is unavailable, SecItemAdd fails with errSecInteractionNotAllowed. This is less obvious. The reason why this fails is that the system needs the key material to protect (by encryption) the keychain item, and it can’t do that if if that key material isn’t available. Update — If you attempt to update a keychain item whose key material is unavailable, SecItemUpdate fails with errSecInteractionNotAllowed. This result is an obvious consequence of the previous result. Delete — Deleting a keychain item, using SecItemDelete, doesn’t require its key material, and thus a delete will succeed when the item is otherwise unavailable. That last point is a significant pitfall. I regularly see keychain code like this: Read an item holding a critical user credential. If that works, use that credential. If it fails, delete the item and start from a ‘factory reset’ state. The problem is that, if your code ends up running in the background unexpectedly, step 1 fails with errSecInteractionNotAllowed and you turn around and delete the user’s credential. Ouch! Note Even if you didn’t write this code, you might have inherited it from a keychain wrapper library. See *Think Before Wrapping, below. There are two paths forward here: If you don’t expect this code to work in the background, check for the errSecInteractionNotAllowed error and non-destructively cancel the operation in that case. If you expect this code to be running in the background, switch to a different data protection level. WARNING For the second path, the most obvious fix is to move from kSecAttrAccessibleWhenUnlocked to kSecAttrAccessibleAfterFirstUnlock. However, this is not a panacea. It’s possible that your app might end up running before first unlock [3]. So, if you choose the second path, you must also make sure to follow the advice for the first path. You can determine whether the device is unlocked using the isProtectedDataAvailable property and its associated notifications. However, it’s best not to use this property as part of your core code, because such preflighting is fundamentally racy. Rather, perform the operation and handle the error gracefully. It might make sense to use isProtectedDataAvailable property as part of debugging, logging, and diagnostic code. [1] For file data protection there’s an entitlement (com.apple.developer.default-data-protection) that controls the default data protection level. There’s no such entitlement for the keychain. That’s actually a good thing! In my experience the file data protection entitlement is an ongoing source of grief. See this thread if you’re curious. [2] This might seem like an odd error but it’s actually pretty reasonable: The operation needs some key material that’s currently unavailable. Only a user action can provide that key material. But the data protection keychain will never prompt the user to unlock their device. Thus you get an error instead. [3] iOS generally avoids running third-party code before first unlock, but there are circumstances where that can happen. The obvious legitimate example of this is a VoIP app, where the user expects their phone to ring even if they haven’t unlocked it since the last restart. There are also other less legitimate examples of this, including historical bugs that caused apps to launch in the background before first unlock. Best Practices With the pitfalls out of the way, let’s talk about best practices. Less Painful Dictionaries I look at a lot of keychain code and it’s amazing how much of it is way more painful than it needs to be. The biggest offender here is the dictionaries. Here are two tips to minimise the pain. First, don’t use CFDictionary. It’s seriously ugly. While the SecItem API is defined in terms of CFDictionary, you don’t have to work with CFDictionary directly. Rather, use NSDictionary and take advantage of the toll-free bridge. For example, consider this CFDictionary code: CFTypeRef keys[4] = { kSecClass, kSecAttrService, kSecMatchLimit, kSecReturnAttributes, }; static const int kTen = 10; CFNumberRef ten = CFNumberCreate(NULL, kCFNumberIntType, &kTen); CFAutorelease(ten); CFTypeRef values[4] = { kSecClassGenericPassword, CFSTR("AYS"), ten, kCFBooleanTrue, }; CFDictionaryRef query = CFDictionaryCreate( NULL, keys, values, 4, &kCFTypeDictionaryKeyCallBacks, &kCFTypeDictionaryValueCallBacks ); Note This might seem rather extreme but I’ve literally seen code like this, and worse, while helping developers. Contrast this to the equivalent NSDictionary code: NSDictionary * query = @{ (__bridge NSString *) kSecClass: (__bridge NSString *) kSecClassGenericPassword, (__bridge NSString *) kSecAttrService: @"AYS", (__bridge NSString *) kSecMatchLimit: @10, (__bridge NSString *) kSecReturnAttributes: @YES, }; Wow, that’s so much better. Second, if you’re working in Swift, take advantage of its awesome ability to create NSDictionary values from Swift dictionary literals. Here’s the equivalent code in Swift: let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecMatchLimit: 10, kSecReturnAttributes: true, ] as NSDictionary Nice! Avoid Reusing Dictionaries I regularly see folks reuse dictionaries for different SecItem calls. For example, they might have code like this: var copyResult: CFTypeRef? = nil let dict = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecReturnData: true, ] as NSMutableDictionary var err = SecItemCopyMatching(dict, &copyResult) if err == errSecItemNotFound { dict[kSecValueData] = Data("opendoor".utf8) err = SecItemAdd(dict, nil) } This specific example will work, but it’s easy to spot the logic error. kSecReturnData is a return type property and it makes no sense to pass it to a SecItemAdd call whose second parameter is nil. I’m not sure why folks do this. I think it’s because they think that constructing dictionaries is expensive. Regardless, this pattern can lead to all sorts of weird problems. For example, it’s the leading cause of the issue described in the Queries and the Uniqueness Constraints section, above. My advice is that you use a new dictionary for each call. That prevents state from one call accidentally leaking into a subsequent call. For example, I’d rewrite the above as: var copyResult: CFTypeRef? = nil let query = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecReturnData: true, ] as NSMutableDictionary var err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { let add = [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", kSecValueData: Data("opendoor".utf8), ] as NSMutableDictionary err = SecItemAdd(add, nil) } It’s a bit longer, but it’s much easier to track the flow. And if you want to eliminate the repetition, use a helper function: func makeDict() -> NSMutableDictionary { [ kSecClass: kSecClassGenericPassword, kSecAttrService: "AYS", kSecAttrAccount: "mrgumby", ] as NSMutableDictionary } var copyResult: CFTypeRef? = nil let query = makeDict() query[kSecReturnData] = true var err = SecItemCopyMatching(query, &copyResult) if err == errSecItemNotFound { let add = makeDict() query[kSecValueData] = Data("opendoor".utf8) err = SecItemAdd(add, nil) } Think Before Wrapping A lot of folks look at the SecItem API and immediately reach for a wrapper library. A keychain wrapper library might seem like a good idea but there are some serious downsides: It adds another dependency to your project. Different subsystems within your project may use different wrappers. The wrapper can obscure the underlying API. Indeed, its entire raison d’être is to obscure the underlying API. This is problematic if things go wrong. I regularly talk to folks with hard-to-debug keychain problems and the conversation goes something like this: Quinn: What attributes do you use in the query dictionary? J R Developer: What’s a query dictionary? Quinn: OK, so what error are you getting back? J R Developer: It throws WrapperKeychainFailedError. That’s not helpful )-: If you do use a wrapper, make sure it has diagnostic support that includes the values passed to and from the SecItem API. Also make sure that, when it fails, it returns an error that includes the underlying keychain error code. These benefits will be particularly useful if you encounter a keychain problem that only shows up in the field. Wrappers must choose whether to be general or specific. A general wrapper may be harder to understand than the equivalent SecItem calls, and it’ll certainly contain a lot of complex code. On the other hand, a specific wrapper may have a model of the keychain that doesn’t align with your requirements. I recommend that you think twice before using a keychain wrapper. Personally I find the SecItem API relatively easy to call, assuming that: I use the techniques shown in Less Painful Dictionaries, above, to avoid having to deal with CFDictionary. I use my secCall(…) helpers to simplify error handling. For the code, see Calling Security Framework from Swift. If you’re not prepared to take the SecItem API neat, consider writing your own wrapper, one that’s tightly focused on the requirements of your project. For example, in my VPN apps I use the wrapper from this post, which does exactly what I need in about 100 lines of code. Prefer to Update Of the four SecItem functions, SecItemUpdate is the most neglected. Rather than calling SecItemUpdate I regularly see folks delete and then re-add the item. This is a shame because SecItemUpdate has some important benefits: It preserves persistent references. If you delete and then re-add the item, you get a new item with a new persistent reference. It’s well aligned with the fundamental database nature of the keychain. It forces you to think about which attributes uniquely identify your item and which items can be updated without changing the item’s identity. Understand These Key Attributes Key items have a number of attributes that are similarly named, and it’s important to keep them straight. I created a cheat sheet for this, namely, SecItem attributes for keys. You wouldn’t believe how often I consult this! Investigating Complex Attributes Some attributes have values where the format is not obvious. For example, the kSecAttrIssuer attributed is documented as: The corresponding value is of type CFData and contains the X.500 issuer name of a certificate. What exactly does that mean? If I want to search the keychain for all certificates issued by a specific certificate authority, what value should I supply? One way to figure this out is to add a certificate to the keychain, read the attributes back, and then dump the kSecAttrIssuer value. For example: let cert: SecCertificate = … let attrs = try secCall { SecItemAdd([ kSecValueRef: cert, kSecReturnAttributes: true, ] as NSDictionary, $0) } as! [String: Any] let issuer = attrs[kSecAttrIssuer as String] as! NSData print((issuer as NSData).debugDescription) // prints: <3110300e 06035504 030c074d 6f757365 4341310b 30090603 55040613 024742> Those bytes represent the contents of a X.509 Name ASN.1 structure with DER encoding. This is without the outer SEQUENCE element, so if you dump it as ASN.1 you’ll get a nice dump of the first SET and then a warning about extra stuff at the end of the file: % xxd issuer.asn1 00000000: 3110 300e 0603 5504 030c 074d 6f75 7365 1.0...U....Mouse 00000010: 4341 310b 3009 0603 5504 0613 0247 42 CA1.0...U....GB % dumpasn1 -p issuer.asn1 SET { SEQUENCE { OBJECT IDENTIFIER commonName (2 5 4 3) UTF8String 'MouseCA' } } Warning: Further data follows ASN.1 data at position 18. Note For details on the Name structure, see section 4.1.2.4 of RFC 5280. Amusingly, if you run the same test against the file-based keychain you’ll… crash. OK, that’s not amusing. It turns out that the code above doesn’t work when targeting the file-based keychain because SecItemAdd doesn’t return a dictionary but rather an array of dictionaries (r. 21111543). Once you get past that, however, you’ll see it print: <301f3110 300e0603 5504030c 074d6f75 73654341 310b3009 06035504 06130247 42> Which is different! Dumping it as ASN.1 shows that it’s the full Name structure, including the outer SEQUENCE element: % xxd issuer-file-based.asn1 00000000: 301f 3110 300e 0603 5504 030c 074d 6f75 0.1.0...U....Mou 00000010: 7365 4341 310b 3009 0603 5504 0613 0247 seCA1.0...U....G 00000020: 42 B % dumpasn1 -p issuer-file-based.asn1 SEQUENCE { SET { SEQUENCE { OBJECT IDENTIFIER commonName (2 5 4 3) UTF8String 'MouseCA' } } SET { SEQUENCE { OBJECT IDENTIFIER countryName (2 5 4 6) PrintableString 'GB' } } } This difference in behaviour between the data protection and file-based keychains is a known bug (r. 26391756) but in this case it’s handy because the file-based keychain behaviour makes it easier to understand the data protection keychain behaviour. Import, Then Add It’s possible to import data directly into the keychain. For example, you might use this code to add a certificate: let certData: Data = … try secCall { SecItemAdd([ kSecClass: kSecClassCertificate, kSecValueData: certData, ] as NSDictionary, nil) } However, it’s better to import the data and then add the resulting credential reference. For example: let certData: Data = … let cert = try secCall { SecCertificateCreateWithData(nil, certData as NSData) } try secCall { SecItemAdd([ kSecValueRef: cert, ] as NSDictionary, nil) } There are two advantages to this: If you get an error, you know whether the problem was with the import step or the add step. It ensures that the resulting keychain item has the correct attributes. This is especially important for keys. These can be packaged in a wide range of formats, so it’s vital to know whether you’re interpreting the key data correctly. I see a lot of code that adds key data directly to the keychain. That’s understandable because, back in the day, this was the only way to import a key on iOS. Fortunately, that’s not been the case since the introduction of SecKeyCreateWithData in iOS 10 and aligned releases. For more information about importing keys, see Importing Cryptographic Keys. App Groups on the Mac Sharing access to keychain items among a collection of apps explains that three entitlements determine your keychain access: keychain-access-groups application-identifier (com.apple.application-identifier on macOS) com.apple.security.application-groups In the discussion of com.apple.security.application-groups it says: Starting in iOS 8, the array of strings given by this entitlement also extends the list of keychain access groups. That’s true, but it’s also potentially misleading. This affordance only works on iOS and its child platforms. It doesn’t work on macOS. That’s because app groups work very differently on macOS than they do on iOS. For all the details, see App Groups: macOS vs iOS: Working Towards Harmony. However, the take-home point is that, when you use the data protection keychain on macOS, your keychain access group list is built from keychain-access-groups and com.apple.application-identifier. Revision History 2025-06-29 Added the Data Protection and Background Execution section. Made other minor editorial changes. 2025-02-03 Added another specific example to the Careful With that Shim, Mac Developer section. 2025-01-29 Added somes specific examples to the Careful With that Shim, Mac Developer section. 2025-01-23 Added the Import, Then Add section. 2024-08-29 Added a discussion of identity formation to the Digital Identities Aren’t Real section. 2024-04-11 Added the App Groups on the Mac section. 2023-10-25 Added the Lost Keychain Items and Lost Keychain Items, Redux sections. 2023-09-22 Made minor editorial changes. 2023-09-12 Fixed various bugs in the revision history. Added the Erroneous Attributes section. 2023-02-22 Fixed the link to the VPNKeychain post. Corrected the name of the Context Matters section. Added the Investigating Complex Attributes section. 2023-01-28 First posted.
Replies
0
Boosts
0
Views
3.9k
Activity
Jun ’25
Is there a way for MDM to push a unique mTLS certificate w/ our Application?
Hi, It may be a stupid question, but we really wonder if there is a way for MDM to push a unique mTLS cert to our iOS application or if it can populate a client certificate in the iOS where our application can access it. Like browser app, how do browser mTLS certs get pushed? Thanks, Ying
Replies
2
Boosts
0
Views
824
Activity
Apr ’25
App Group Not working as intended after updating to macOS 15 beta.
I have an app (currently not released on App Store) which runs on both iOS and macOS. The app has widgets for both iOS and macOS which uses user preference (set in app) into account while showing data. Before upgrading to macOS 15 (until Sonoma) widgets were working fine and app was launching correctly, but after upgrading to macOS 15 Sequoia, every time I launch the app it give popup saying '“Kontest” would like to access data from other apps. Keeping app data separate makes it easier to manage your privacy and security.' and also widgets do not get user preferences and throw the same type of error on Console application when using logging. My App group for both iOS and macOS is 'group.com.xxxxxx.yyyyy'. I am calling it as 'UserDefaults(suiteName: Constants.userDefaultsGroupID)!.bool(forKey: "shouldFetchAllEventsFromCalendar")'. Can anyone tell, what am I doing wrong here?
Replies
26
Boosts
9
Views
5k
Activity
Oct ’25
`cp` ( & friends ) silent loss of extended attributes & file flags
Since the introduction of the siblings / and /System/Volumes/Data architecture, some very basic, critical commands seems to have a broken behaviour ( cp, rsync, tar, cpio…). As an example, ditto which was introduced more than 10 years ago to integrate correctly all the peculiarity of HFS Apple filesystem as compared to the UFS Unix filesystem is not behaving correctly. For example, from man ditto: --rsrc Preserve resource forks and HFS meta-data. ditto will store this data in Carbon-compatible ._ AppleDouble files on filesystems that do not natively support resource forks. As of Mac OS X 10.4, --rsrc is default behavior. [...] --extattr Preserve extended attributes (requires --rsrc). As of Mac OS X 10.5, --extattr is the default. and nonetheless: # ls -@delO /private/var/db/ConfigurationProfiles/Store drwx------@ 5 root wheel datavault 160 Jan 20 2024 /private/var/db/ConfigurationProfiles/Store                            ********* com.apple.rootless 28 *************************** # mkdir tmp # ditto /private/var/db/ConfigurationProfiles tmp ditto: /Users/alice/Security/Admin/Apple/APFS/tmp/Settings: Operation not permitted ditto: /Users/alice/Security/Admin/Apple/APFS/tmp/Store: Operation not permitted # ls -@delO tmp/Store drwx------ 5 root wheel - 160 Aug 8 13:55 tmp/Store                            * # The extended attribute on copied directory Store is empty, the file flags are missing, not preserved as documented and as usual behaviour of ditto was since a long time ( macOS 10.5 ). cp, rsync, tar, cpio exhibit the same misbehaviour. But I was using ditto to be sure to avoid any incompatibility with the Apple FS propriaitary modifications. As a consequence, all backup scripts and applications are failing more or less silently, and provide corrupted copies of files or directories. ( I was here investigating why one of my security backup shell script was making corrupted backups, and only on macOS ). How to recover the standard behaviour --extattr working on modern macOS?
Replies
4
Boosts
0
Views
1.1k
Activity
Feb ’26
MFA MacOS At ScreenSaver (Lock Screen).
Hi , I did The MFA(2FA) of Email OTP For MacOS Login Screen using, Authorization Plugin, Using This git hub project. It is working For Login Screen , Im trying to Add The Same plugin for LockScreen but it is not working at lock Screen , Below is the reffrense theard For The issue , https://developer.apple.com/forums/thread/127614, please Share The Code that should Present the NSwindow at Screen Saver (Lock Screen) MacOS .
Replies
3
Boosts
0
Views
972
Activity
5d
setCodeSigningRequirement seems not to work in new Service Management API setup.
I have developed a sample app following the example found Updating your app package installer to use the new Service Management API and referring this discussion on XPC Security. The app is working fine, I have used Swift NSXPCConnection in favour of xpc_connection_create_mach_service used in the example. (I am running app directly from Xcode) I am trying to set up security requirements for the client connection using setCodeSigningRequirement on the connection instance. But it fails for even basic requirement connection.setCodeSigningRequirement("anchor apple"). Error is as follows. cannot open file at line 46986 of [554764a6e7] os_unix.c:46986: (0) open(/private/var/db/DetachedSignatures) - Undefined error: 0 xpc_support_check_token: anchor apple error: Error Domain=NSOSStatusErrorDomain Code=-67050 "(null)" status: -67050 I have used codesign -d --verbose=4 /path/to/executable to check the attributes I do get them in the terminal. Other way round, I have tried XPC service provider sending back process id (pid) with each request, and I am probing this id to get attributes using this code which gives all the details. func inspectCodeSignature(ofPIDString pidString: String) { guard let pid = pid_t(pidString) else { print("Invalid PID string: \(pidString)") return } let attributes = [kSecGuestAttributePid: pid] as CFDictionary var codeRef: SecCode? let status = SecCodeCopyGuestWithAttributes(nil, attributes, [], &codeRef) guard status == errSecSuccess, let code = codeRef else { print("Failed to get SecCode for PID \(pid) (status: \(status))") return } var staticCode: SecStaticCode? let staticStatus = SecCodeCopyStaticCode(code, [], &staticCode) guard staticStatus == errSecSuccess, let staticCodeRef = staticCode else { print("Failed to get SecStaticCode (status: \(staticStatus))") return } var infoDict: CFDictionary? if SecCodeCopySigningInformation(staticCodeRef, SecCSFlags(rawValue: kSecCSSigningInformation), &infoDict) == errSecSuccess, let info = infoDict as? [String: Any] { print("🔍 Code Signing Info for PID \(pid):") print("• Identifier: \(info["identifier"] ?? "N/A")") print("• Team ID: \(info["teamid"] ?? "N/A")") if let entitlements = info["entitlements-dict"] as? [String: Any] { print("• Entitlements:") for (key, value) in entitlements { print(" - \(key): \(value)") } } } else { print("Failed to retrieve signing information.") } var requirement: SecRequirement? if SecRequirementCreateWithString("anchor apple" as CFString, [], &requirement) == errSecSuccess, let req = requirement { let result = SecStaticCodeCheckValidity(staticCodeRef, [], req) if result == errSecSuccess { print("Signature is trusted (anchor apple)") } else { print("Signature is NOT trusted by Apple (failed anchor check)") } } var infoDict1: CFDictionary? let signingStatus = SecCodeCopySigningInformation(staticCodeRef, SecCSFlags(rawValue: kSecCSSigningInformation), &infoDict1) guard signingStatus == errSecSuccess, let info = infoDict1 as? [String: Any] else { print("Failed to retrieve signing information.") return } print("🔍 Signing Info for PID \(pid):") for (key, value) in info.sorted(by: { $0.key < $1.key }) { print("• \(key): \(value)") } } If connection.setCodeSigningRequirement does not works I plan to use above logic as backup. Q: Please advise is there some setting required to be enabled or I have to sign code with some flags enabled. Note: My app is not running in a Sandbox or Hardened Runtime, which I want.
Replies
12
Boosts
0
Views
378
Activity
Apr ’25
Auth Plugin Timeout Issue During Screen Unlock
Hi! We are developing an authentication plugin for macOS that integrates with the system's authentication flow. The plugin is designed to prompt the user for approval via a push notification in our app before allowing access. The plugin is added as the first mechanism in the authenticate rule, followed by the default builtin:authenticate as a fallback. When the system requests authentication (e.g., during screen unlock), our plugin successfully displays the custom UI and sends a push notification to the user's device. However, I've encountered the following issue: If the user does not approve the push notification within ~30 seconds, the system resets the screen lock (expected behavior). If the user approves the push notification within approximately 30 seconds but doesn’t start entering their password before the timeout expires, the system still resets the screen lock before they can enter their password, effectively canceling the session. What I've Tried: Attempted to imitate mouse movement after the push button was clicked to keep the session active. Created a display sleep prevention assertion using IOKit to prevent the screen from turning off. Used the caffeinate command to keep the display and system awake. Tried setting the result as allow for the authorization request and passing an empty password to prevent the display from turning off. I also checked the system logs when this issue occurred and found the following messages: ___loginwindow: -[LWScreenLock (Private) askForPasswordSecAgent] | localUser = >timeout loginwindow: -[LWScreenLock handleUnlockResult:] _block_invoke | ERROR: Unexpected _lockRequestedBy of:7 sleeping screen loginwindow: SleepDisplay | enter powerd: Process (loginwindow) is requesting display idle___ These messages suggest that the loginwindow process encounters a timeout condition, followed by the display entering sleep mode. Despite my attempts to prevent this behavior, the screen lock still resets prematurely. Questions: Is there a documented (or undocumented) system timeout for the entire authentication flow during screen unlock that I cannot override? Are there any strategies for pausing or extending the authentication timeout to allow for complex authentication flows like push notifications? Any guidance or insights would be greatly appreciated. Thank you!
Replies
3
Boosts
2
Views
351
Activity
Jun ’25
Login Keychain Access Autmation
I have been trying to find a way to be able to sign some data with private key of an identity in login keychain without raising any prompts. I am able to do this with system keychain (obviously with correct permissions and checks) but not with login keychain. It always ends up asking user for their login password. Here is how the code looks, roughly, NSDictionary *query = @{ (__bridge id)kSecClass: (__bridge id)kSecClassIdentity, (__bridge id)kSecReturnRef: @YES, (__bridge id)kSecMatchLimit: (__bridge id)kSecMatchLimitAll }; CFTypeRef result = NULL; OSStatus status = SecItemCopyMatching((__bridge CFDictionaryRef)query, (CFTypeRef *)&amp;amp;result); NSArray *identities = ( NSArray *)result; SecIdentityRef identity = NULL; for (id _ident in identities) { // pick one as required } SecKeyRef privateKey = NULL; OSStatus status = SecIdentityCopyPrivateKey(identity, &amp;amp;privateKey); NSData *strData = [string dataUsingEncoding:NSUTF8StringEncoding]; unsigned char hash[CC_SHA256_DIGEST_LENGTH]; CC_SHA256(strData.bytes, (CC_LONG)strData.length, hash); NSData *digestData = [NSData dataWithBytes:hash length:CC_SHA256_DIGEST_LENGTH]; CFErrorRef cfError = NULL; NSData *signature = (__bridge_transfer NSData *)SecKeyCreateSignature(privateKey, kSecKeyAlgorithmRSASignatureDigestPKCS1v15SHA256, (__bridge CFDataRef)digestData, &amp;amp;cfError); Above code raises these system logs in console default 08:44:52.781024+0000 securityd client is valid, proceeding default 08:44:52.781172+0000 securityd code requirement check failed (-67050), client is not Apple-signed default 08:44:52.781233+0000 securityd displaying keychain prompt for /Applications/Demo.app(81692) If the key is in login keychain, is there any way to do SecKeyCreateSignature without raising prompts? What does client is not Apple-signed mean? PS: Identities are pre-installed either manually or via some device management solution, the application is not installing them.
Replies
3
Boosts
0
Views
178
Activity
Apr ’25
Unsandboxed app can't modify other app
I work for Brave, a browser with ~80M users. We want to introduce a new system for automatic updates called Omaha 4 (O4). It's the same system that powers automatic updates in Chrome. O4 runs as a separate application on users' systems. For Chrome, this works as follows: An app called GoogleUpdater.app regularly checks for updates in the background. When a new version is found, then GoogleUpdater.app installs it into Chrome's installation directory /Applications/Google Chrome.app. But consider what this means: A separate application, GoogleUpdater.app, is able to modify Google Chrome.app. This is especially surprising because, for example, the built-in Terminal.app is not able to modify Google Chrome.app. Here's how you can check this for yourself: (Re-)install Chrome with its DMG installer. Run the following command in Terminal: mkdir /Applications/Google\ Chrome.app/test. This works. Undo the command: rm -rf /Applications/Google\ Chrome.app/test Start Chrome and close it again. mkdir /Applications/Google\ Chrome.app/test now fails with "Operation not permitted". (These steps assume that Terminal does not have Full Disk Access and System Integrity Protection is enabled.) In other words, once Chrome was started at least once, another application (Terminal in this case) is no longer allowed to modify it. But at the same time, GoogleUpdater.app is able to modify Chrome. It regularly applies updates to the browser. For each update, this process begins with an mkdir call similarly to the one shown above. How is this possible? What is it in macOS that lets GoogleUpdater.app modify Chrome, but not another app such as Terminal? Note that Terminal is not sandboxed. I've checked that it's not related to codesigning or notarization issues. In our case, the main application (Brave) and the updater (BraveUpdater) are signed and notarized with the same certificate and have equivalent requirements, entitlements and provisioning profiles as Chrome and GoogleUpdater. The error that shows up in the Console for the disallowed mkdir call is: kernel (Sandbox) System Policy: mkdir(8917) deny(1) file-write-create /Applications/Google Chrome.app/foo (It's a similar error when BraveUpdater tries to install a new version into /Applications/Brave Browser.app.) The error goes away when I disable System Integrity Protection. But of course, we cannot ask users to do that. Any help would be greatly appreciated.
Replies
4
Boosts
0
Views
310
Activity
May ’25
API: SecPKCS12Import; error code: -25264; error message: MAC verification failed during PKCS12 import (wrong password?)
Problem Statement: Pre-requisite is to generate a PKCS#12 file using openssl 3.x or above. Note: I have created a sample cert, but unable to upload it to this thread. Let me know if there is a different way I can upload. When trying to import a p12 certificate (generated using openssl 3.x) using SecPKCS12Import on MacOS (tried on Ventura, Sonoma, Sequoia). It is failing with the error code: -25264 and error message: MAC verification failed during PKCS12 import (wrong password?). I have tried importing in multiple ways through, Security Framework API (SecPKCS12Import) CLI (security import &lt;cert_name&gt; -k ~/Library/Keychains/login.keychain -P "&lt;password&gt;”) Drag and drop in to the Keychain Application All of them fail to import the p12 cert. RCA: The issues seems to be due to the difference in the MAC algorithm. The MAC algorithm used in the modern certs (by OpenSSL3 is SHA-256) which is not supported by the APPLE’s Security Framework. The keychain seems to be expecting the MAC algorithm to be SHA-1. Workaround: The current workaround is to convert the modern p12 cert to a legacy format (using openssl legacy provider which uses openssl 1.1.x consisting of insecure algorithms) which the SecPKCS12Import API understands. I have created a sample code using references from another similar thread (https://developer.apple.com/forums/thread/723242) from 2023. The steps to compile and execute the sample is mentioned in the same file. PFA the sample code by the name “pkcs12_modern_to_legacy_converter.cpp”. Also PFA a sample certificate which will help reproduce the issue by the name “modern_certificate.p12” whose password is “export”. Questions: Is there a fix on this issue? If yes, pls guide me through it; else, is it expected to be fixed in the future releases? Is there a different way to import the p12 cert which is resistant to the issue? This issue also poses a security concerns on using outdated cryptographic algorithms. Kindly share your thoughts. pkcs12_modern_to_legacy_converter.cpp
Replies
11
Boosts
0
Views
506
Activity
Apr ’25
Clang warning about 'xar_open' API deprecation in macOS 12.0. How to address/replace with a more approprite API?
Hello! We have code that extracts macOS Installer package (.pkg, .mpkg) signature information using APIs defined in <xar/xar.h> The code opens the package using ‘xar_open’ API like this. func open(file: String) throws(XarError) { xarfile = xar_open(file, READ) if xarfile == nil { throw .fileOpenError } } This code produces a clang warning in our CI build system when built for macOS 12 and up. 'xar_open' was deprecated in macOS 12.0: xar is a deprecated file format and should not be used. Question #1: What is the appropriate / more preferred way to extract signature information from an Installer package given that xar related APIs are deprecated? We use xar APIs to validate the package signature prior to installation to prevent packagers not signed by our team ID from being installed. Question #2: “xar is a deprecated file format and should not be used.”. Does this phrase refer to the file format that should be avoided or the API that extract signature information? We distribute our product using Developer ID method that using pkg/mpkg formats which I believe internally follow the same structure as xar files. I hope this message does not mean we should rethink the distribution method for our products. Thank you. Filed FB FB17148233 as well.
Replies
10
Boosts
0
Views
433
Activity
Apr ’25
How to Localize Biometric Prompt for SecKeyCreateSignature with Secure Enclave
I'm using Secure Enclave to generate and use a private key like this: let access = SecAccessControlCreateWithFlags(nil, kSecAttrAccessibleWhenUnlockedThisDeviceOnly, [.privateKeyUsage, .biometryAny], nil) let attributes: [String: Any] = [ kSecAttrKeyType as String: kSecAttrKeyTypeECSECPrimeRandom, kSecAttrKeySizeInBits as String: 256, kSecAttrTokenID as String: kSecAttrTokenIDSecureEnclave, kSecAttrAccessControl as String: access as Any, kSecAttrApplicationTag as String: "com.example.key".data(using: .utf8)!, kSecReturnRef as String: true ] let privateKey = SecKeyCreateRandomKey(attributes as CFDictionary, nil) Later, I use this key to sign a message: let signature = SecKeyCreateSignature(privateKey, .ecdsaSignatureMessageX962SHA256, dataToSign as CFData, nil) This prompts for biometric authentication, but shows the default system text. How can I customize or localize the biometric prompt (e.g., title, description, button text) shown during SecKeyCreateSignature? Thanks!
Replies
1
Boosts
0
Views
120
Activity
Apr ’25
iOS 18.4 key usage requirements fails TLS connections
iOS 18.4 introduced some requirements on the Key Usage of 802.1x server certificates, as described here. https://support.apple.com/en-us/121158 When using TLS_ECDHE_RSA or TLS_DHE_RSA cipher suites, 802.1X server certificates containing a Key Usage extension must have Digital Signature key usage set. When using the TLS_RSA cipher suite, 802.1X server certificates containing a Key Usage extension must have Key Encipherment key usage set. It reads like the change is supposed to affect 802.1x only. However, we have found out that the new restrictions are actually imposed on all TLS connections using the Network framework, including in Safari. Unlike other certificate errors which can be either ignored by users (as in Safari) or by code (via sec_protocol_options_set_verify_block), these new ones can't. Even if passing completion(true) in the TLS verification block, the connection still ends up in waiting state with error -9830: illegal parameter. I understand that these requirements are valid ones but as a generic TLS library I also expect that Network framework could at least allow overriding the behavior. The current treatment is not consistent with those on other certificate errors. Since I can't upload certificates, here is how to reproduce a certificate that fails. Create a OpenSSL config file test.cnf [ req ] default_bits = 2048 distinguished_name = dn x509_extensions = v3_ca prompt = no [ dn ] CN = example.com [ v3_ca ] subjectKeyIdentifier = hash authorityKeyIdentifier = keyid:always,issuer basicConstraints = CA:TRUE keyUsage = critical, keyCertSign, cRLSign Generate certificate and private key openssl req -x509 -new -nodes -keyout key.pem -out cert.pem -days 365 -config test.cnf And here is the client code to test. // Target server and port let host = NWEndpoint.Host("example.com") let port = NWEndpoint.Port("443")! // Configure insecure TLS options let tlsOptions = NWProtocolTLS.Options() sec_protocol_options_set_verify_block(tlsOptions.securityProtocolOptions, { _, _, completion in // Always trust completion(true) }, DispatchQueue.global()) let params = NWParameters(tls: tlsOptions) let connection = NWConnection(host: .init(host), port: .init(rawValue: port)!, using: params) connection.stateUpdateHandler = { newState in switch newState { case .ready: print("TLS connection established") case .failed(let error): print("Connection failed: \(error)") case .cancelled: print("Connection canceled") case .preparing: print("Connection preparing") case .waiting(let error): print("Connection waiting: \(error)") case .setup: print("Connection setup") default: break } } connection.start(queue: .global()) Output Connection preparing Connection waiting: -9830: illegal parameter Previously reported as FB17099740
Replies
5
Boosts
0
Views
302
Activity
Apr ’25