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

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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.
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8.1k
Nov ’25
Is “webcredentials” required for HTTPS callbacks in ASWebAuthenticationSession?
Hello, When using ASWebAuthenticationSession with an HTTPS callback URL (Universal Link), I receive the following error: Authorization error: The operation couldn't be completed. Application with identifier jp.xxxx.yyyy.dev is not associated with domain xxxx-example.go.link. Using HTTPS callbacks requires Associated Domains using the webcredentials service type for xxxx-example.go.link. I checked Apple’s official documentation but couldn’t find any clear statement that webcredentials is required when using HTTPS callbacks in ASWebAuthenticationSession. What I’d like to confirm: Is webcredentials officially required when using HTTPS as a callback URL with ASWebAuthenticationSession? If so, is there any official documentation or technical note that states this requirement? Environment iOS 18.6.2 Xcode 16.4 Any clarification or official references would be greatly appreciated. Thank you.
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224
Nov ’25
ATS on watchOS is fundamentally broken for generic client apps. Why is Apple killing innovation?
I spent the entire day debugging a network issue on my Apple Watch app, only to realize the problem isn't my code—it's Apple's inflexible design. The Context: I am building a generic MCP (Model Context Protocol) client for watchOS. The nature of this app is to allow users to input their own server URLs (e.g., a self-hosted endpoint, or public services like GitHub's MCP server) to interact with LLMs and tools. The Problem: When using standard URLSession to connect to widely trusted, public HTTPS endpoints (specifically GitHub's official MCP server at https://mcp.github.com), the connection is forcefully terminated by the OS with NSURLErrorDomain Code=-1200 (TLS handshake failed). The Analysis: This is caused by App Transport Security (ATS). ATS is enforcing a draconian set of security standards (specific ciphers, forward secrecy requirements, etc.) that many perfectly valid, secure, and globally accepted servers do not strictly meet 100%. The Absurdity: We cannot whitelist domains: Since this is a generic client, I cannot add NSExceptionDomains to Info.plist because I don't know what URL the user will input. We cannot disable ATS: Adding NSAllowsArbitraryLoads is a guaranteed rejection during App Store review for a general-purpose app without a "compelling reason" acceptable to Apple. The result: My app is effectively bricked. It cannot connect to GitHub. It cannot connect to 90% of the user's self-hosted servers. The Question: Is the Apple Watch just a toy? How does Apple expect us to build flexible, professional tools when the OS acts like a nanny that blocks connections to GitHub? We need a way to bypass strict ATS checks for user-initiated connections in generic network tools, similar to how curl -k or other developer tools work. The current "all-or-nothing" policy is suffocating.
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Nov ’25
FIDO2 USB Monitoring using custom Authorization Plugin
I'm looking to implement USB monitoring for FIDO2 authentication through a custom Authorization Plugin, specifically for the below ones. This plugin applies to the following macOS authorization mechanisms: system.login.console — login window authentication system.login.screensaver — screensaver unlock authentication The goal is to build a GUI AuthPlugin, an authorization plugin that presents a custom window prompting the user to "Insert your FIDO key”. Additionally, the plugin should detect when the FIDO2 device is removed and respond accordingly. Additional Info: We have already developed a custom authorization plugin which is a primary authentication using OTP at login and Lock Screen. We are now extending to include FIDO2 support as a primary. Our custom authorization plugin is designed to replace the default loginwindow:login mechanism with a custom implementation. Question: Is there a reliable approach to achieve the USB monitoring functionality through a custom authorization plugin? Any guidance or pointers on this would be greatly appreciated.
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818
Nov ’25
Archived app failing to get root certificates for SSL websocket connection
I've had a Unreal Engine project that uses libwebsocket to make a websocket connection with SSL to a server. Recently I made a build using Unreal Engine 5.4.4 on MacOS Sequoia 15.5 and XCode 16.4 and for some reason the websocket connection now fails because it can't get the local issuer certificate. It fails to access the root certificate store on my device (Even though, running the project in the Unreal Editor works fine, it's only when making a packaged build with XCode that it breaks) I am not sure why this is suddenly happening now. If I run it in the Unreal editor on my macOS it works fine and connects. But when I make a packaged build which uses XCode to build, it can't get the local issuer certificate. I tried different code signing options, such as sign to run locally or just using sign automatically with a valid team, but I'm not sure if code signing is the cause of this issue or not. This app is only for development and not meant to be published, so that's why I had been using sign to run locally, and that used to work fine but not anymore. Any guidance would be appreciated, also any information on what may have changed that now causes this certificate issue to happen. I know Apple made changes and has made notarizing MacOS apps mandatory, but I'm not sure if that also means a non-notarized app will now no longer have access to the root certificate store of a device, in my research I haven't found anything about that specifically, but I'm wondering if any Apple engineers might know something about this that hasn't been put out publicly.
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142
Nov ’25
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"
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3.6k
Nov ’25
Full disk access for CLI app
It seems it is not possible to give a CLI app (non .app bundle) full disk access in macOS 26.1. This seems like a bug and if not that is a breaking change. Anybody seeing the same problem? Our application needs full disk access for a service running as a LaunchDaemon. The binary is located in a /Library subfolder.
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718
Nov ’25
How to install self signed certificate to iPhone simulator running iOS 18.5?
I am trying to communicate with the backend of my project. So I need to install the certificate into the simulator. I have the .pem file but when I drag-dropped it into the simulator, I got the error "Simulator device failed to complete the requested operation.". The simulator is an iPhone 16 Pro running iOS 18.5. Is there any way to install the cert to my simulator? PS: I can't use Apple Configurator or MDM because I am using the office's Mac. And I can't install anything there. So I can only do it manually.
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364
Nov ’25
iOS App Fails to Establish Secure Connection (NSURLErrorDomain Code=-1200 SSL Error)
Hi everyone 👋 I’m running into a persistent SSL issue on iOS where the app fails to establish a secure HTTPS connection to our backend APIs. The same endpoints work fine on Android and web, but on iOS the requests fail with: Error Domain=NSURLErrorDomain Code=-1200 "An SSL error has occurred and a secure connection to the server cannot be made." UserInfo={ NSLocalizedDescription = "An SSL error has occurred and a secure connection to the server cannot be made."; _kCFStreamErrorDomainKey = 3; _kCFStreamErrorCodeKey = -9802; } 🔍 What I’ve Checked: The servers use valid, trusted SSL certificates from a public CA TLS 1.2 and 1.3 are enabled The intermediate certificates appear correctly configured (verified using SSL Labs) The issue happens on our customer's end. (Got it via Sentry) Note: We recently removed NSAppTransportSecurity(NSAllowsArbitraryLoads) on our app, since all the endpoints use valid HTTPS certificates and standard configurations. ❓ Questions: Are there additional SSL validation checks performed by iOS when ATS is enabled? Has anyone seen similar behaviour, where valid certificate chains still trigger SSL errors? Any insights or debugging suggestions would be greatly appreciated 🙏
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200
Oct ’25
How to debug SecurityAgentPlugins?
Hi, I’ve developed a custom Authorization Plugin and placed it under: /Library/Security/SecurityAgentPlugins/AuthPlugin.bundle I also updated the corresponding right in the authorization database (authorizationdb) to point to my plugin’s mechanism. However, when I invoke the right, my plugin does not get loaded. The system log shows the following errors: AuthorizationHostHelper: Init: unable to load bundle executable for plugin: AuthPlugin.bundle AuthorizationHostHelper: Processing request: Failed to create agent mechanism AuthPlugin:auth.startup.authenticate, failing authentication! Here’s what I’ve verified so far: The plugin bundle and its executable are signed and notarized successfully. The executable inside the bundle is universal (arm64 + x86_64). The bundle structure looks correct (Contents/Info.plist, Contents/MacOS/..., etc.). Despite that, the plugin fails to load at runtime. Could anyone provide advice on how to debug or trace why the SecurityAgent cannot load the bundle executable? Are there any entitlements, permissions, or SIP-related restrictions that might prevent custom authorization plugins from being loaded on modern macOS versions? Thanks in advance for any insights!
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68
Oct ’25
Avoid repeated authorization dialogs when changing network settings
I have an swift command line tool that changes proxy settings in system preferences via SystemConfiguration framework, does some stuff, and in the end reverts proxy settings back to original. Here is simplified code: var authorization: AuthorizationRef? let status = AuthorizationCreate(nil, nil, [], &authorization) let prefs = SCPreferencesCreateWithAuthorization(nil, "myapp" as CFString, nil, authorization) // change proxy setttings // do some stuff let prefs2 = SCPreferencesCreateWithAuthorization(nil, "myapp" as CFString, nil, authorization) // change proxy settings back to original When I try to change settings for the first time, the system dialog appears requesting permission to change network settings. If I try to change settings again within а short period of time, the dialog does not appear again. However, if it takes more than several minutes after first change, the dialog does appear again. Is there a way to create authorization, so that the dialog appears only once per app launch, no matter how much time passed since the first dialog?
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324
Oct ’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?
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4.9k
Oct ’25
How to protect endpoints used by Message Filtering Extension?
Hi, I am just wondering if there is any option to protect my endpoints that will be used by Message Filtering Extension? According to the documentation our API has 2 endpoints: /.well-known/apple-app-site-association /[endpoint setup in the ILMessageFilterExtensionNetworkURL value of the Info.plist file] that the deferQueryRequestToNetwork will request on every message Since all requests to these 2 endpoints are made by iOS itself (deferQueryRequestToNetwork), I don't understand how I can protect these endpoints on my side, like API key, or maybe mTLS. The only way that I found is white list for Apple IP range. Is there other methods for it?
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144
Oct ’25
iOS 26 - S/MIME Encryption / Certificates
Hi everyone. Since the update to iOS 26, we are no longer able to tap the person's name and view the certificate of a signed email and choose to install the certificate or remove it. This has always worked just fine but seems to be broken on iOS 26 and I have verified that it does not work on iOS 26.1 beta as well. The part that is strange is it does work just fine on an iPad running iPad OS 26. This makes it impossible to send encrypted emails to someone via the mail app on an iPhone. I have found a temporary workaround which is to install Outlook for iOS and install the certificates through that app which then allows me to send encrypted emails via Outlook. This appears to be a bug just with the iPhone as I have also seen a few other people online talking about the same problem. Has anyone found a solution to this?
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738
Oct ’25
Entitlement values for the Enhanced Security and the Additional Runtime Platform Restrictions
I recently turned on the enhanced security options for my macOS app in Xcode 26.0.1 by adding the Enhanced Security capability in the Signing and Capabilities tab. Then, Xcode adds the following key-value sets (with some other key-values) to my app's entitlements file. <key>com.apple.security.hardened-process.enhanced-security-version</key> <integer>1</integer> <key>com.apple.security.hardened-process.platform-restrictions</key> <integer>2</integer> These values appear following the documentation about the enhanced security feature (Enabling enhanced security for your app) and the app works without any issues. However, when I submitted a new version to the Mac App Store, my submission was rejected, and I received the following message from the App Review team via the App Store Connect. Guideline 2.4.5(i) - Performance Your app incorrectly implements sandboxing, or it contains one or more entitlements with invalid values. Please review the included entitlements and sandboxing documentation and resolve this issue before resubmitting a new binary. Entitlement "com.apple.security.hardened-process.enhanced-security-version" value must be boolean and true. Entitlement "com.apple.security.hardened-process.platform-restrictions" value must be boolean and true. When I changed those values directly in the entitlements file based on this message, the app appears to still work. However, these settings are against the description in the documentation I mentioned above and against the settings Xcode inserted after changing the GUI setting view. So, my question is, which settings are actually correct to enable the Enhanced Security and the Additional Runtime Platform Restrictions?
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980
Oct ’25
How to detect or opt out of iOS app prewarming?
Hi, We are running into issues with iOS app prewarming, where the system launches our app before the user has entered their passcode. In our case, the app stores flags, counters, and session data in UserDefaults and the Keychain. During prewarm launches: UserDefaults only returns default values (nil, 0, false). We have no way of knowing whether this information is valid or just a placeholder caused by prewarming. Keychain items with kSecAttrAccessibleAfterFirstUnlockThisDeviceOnly are inaccessible, which can lead to broken business logic (the app can assume no session exists). No special launch options or environment variables appear to be set. We can reproduce this 100% of the time by starting a Live Activity in the app before reboot. Here’s an example of the workaround we tried, following older recommendations: __attribute__((constructor)) static void ModuleInitializer(void) { char* isPrewarm = getenv("ActivePrewarm"); if (isPrewarm != NULL && isPrewarm[0] == '1') { exit(0); // prevent prewarm launch from proceeding } } On iOS 16+, the ActivePrewarm environment variable doesn’t seem to exist anymore (though older docs and SDKs such as Sentry reference it). We also tried listening for UIApplication.protectedDataDidBecomeAvailableNotification, but this is not specific to prewarming (it also fires when the device gets unlocked) and can cause watchdog termination if we delay work too long. Questions: Is there a supported way to opt out of app prewarming? What is the correct way to detect when an app is being prewarmed? Is the ActivePrewarm environment variable still supported in iOS 16+? Ideally, the UserDefaults API itself should indicate whether it is returning valid stored values or defaults due to the app being launched in a prewarm session. We understand opting out may impact performance, but data security and integrity are our priority. Any guidance would be greatly appreciated.
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189
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
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