Background I've repeatedly run into codesigning (and missing provisioning profile) issues for my Ruby/Glimmer app and am looking for ways to troubleshoot this outside of Xcode. The app structure is as follows: PATHmanager.app └── Contents ├── Info.plist ├── MacOS │   └── PATHmanager ├── PkgInfo ├── Resources │   └── AppIcon.icns ├── _CodeSignature │   └── CodeResources └── embedded.provisionprofile Architecture I have a Mac mini Apple M2 Pro with macOS Ventura 13.4. Xcode is not used directly, but the underlying command line tools (e.g., codesign, productbuild, pkgutil, xcrun) are run from a custom Ruby script. xcodebuild -version Xcode 14.3.1 Build version 14E300c Questions Is the .app directory and file structure/naming sufficient? If not, can you point me in the direction of a minimal example that does not use Xcode? Info.plist is an XML text document (not binary), which I believe is in an acceptable format, but how do I lint this file and determine if it contains all of the necessary key/value pairs? <?xml version="1.0" encoding="UTF-8"?> <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd"> <plist version="1.0"> <dict> <key>CFBundleDevelopmentRegion</key> <string>en</string> <key>CFBundleDisplayName</key> <string>PATH manager</string> <key>CFBundleExecutable</key> <string>PATHmanager</string> <key>CFBundleIconFile</key> <string>AppIcon.icns</string> <key>CFBundleIdentifier</key> <string>com.chipcastle.pathmanager</string> <key>CFBundleInfoDictionaryVersion</key> <string>6.0</string> <key>CFBundleName</key> <string>PATHmanager</string> <key>CFBundlePackageType</key> <string>APPL</string> <key>CFBundleShortVersionString</key> <string>1.15</string> <key>CFBundleSupportedPlatforms</key> <array> <string>MacOSX</string> </array> <key>CFBundleVersion</key> <string>1.15</string> <key>ITSAppUsesNonExemptEncryption</key> <false/> <key>LSApplicationCategoryType</key> <string>public.app-category.developer-tools</string> <key>LSMinimumSystemVersion</key> <string>12.0</string> <key>LSUIElement</key> <false/> <key>NSAppTransportSecurity</key> <dict> <key>NSAllowsArbitraryLoads</key> <true/> </dict> <key>NSHumanReadableCopyright</key> <string>© 2025 Chip Castle Dot Com, Inc.</string> <key>NSMainNibFile</key> <string>MainMenu</string> <key>NSPrincipalClass</key> <string>NSApplication</string> </dict> </plist> PATHmanager is a Mach-O 64-bit executable arm64 file created by using Tebako. Does this executable need to be codesigned, or is codesigning the .app folder sufficient? Does the .app directory need an entitlements file? Here's how I codesign it: codesign --deep --force --verify --verbose=4 --options runtime --timestamp --sign 'Apple Distribution: Chip Castle Dot Com, Inc. (BXN9N7MNU3)' '/Users/chip/Desktop/distribution/PATHmanager.app' Does the PATHmanager binary need an entitlements file? Here's how I codesign it: codesign --deep --force --verify --verbose=4 --options runtime --timestamp --entitlements '/Users/chip/Desktop/PATHmanager.entitlements' --sign 'Apple Distribution: Chip Castle Dot Com, Inc. (BXN9N7MNU3)' '/Users/chip/Desktop/distribution/PATHmanager.app/Contents/MacOS/PATHmanager' How can I verify what entitlements, if any, are required for codesigning the binary? The PATHmanager.entitlements file is an XML text file containing only the following: <?xml version="1.0" encoding="UTF-8"?> <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd"> <plist version="1.0"> <dict> <key>com.apple.security.app-sandbox</key> <true/> </dict> </plist> Is the embedded.provisionprofile necessary, and if so, how do I know determine if it matches the certificate or entitlements that I'm using? Additionally, is it named and located properly? I submitted this to the AppStore several weeks ago and the reviewer reported that the executable would not load on their machine (even though it worked on mine.) Is it better for me to release via TestFlight for testing, and if so, do I need to following a separate process for codesigning (i.e., using different entitlements, profiles, certs, etc) when doing so? I've been playing whack-a-mole with this for too long to mention and am hoping to nail down a better deployment flow, so any suggestions for improvement will be greatly appreciated. Thank you in advance.