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How to Programmatically Install and Trust Root Certificate in System Keychain
I am developing a macOS application (targeting macOS 13 and later) that is non-sandboxed and needs to install and trust a root certificate by adding it to the System keychain programmatically. I’m fine with prompting the user for admin privileges or password, if needed. So far, I have attempted to execute the following command programmatically from both: A user-level process A root-level process sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /path/to/cert.pem While the certificate does get installed, it does not appear as trusted in the Keychain Access app. One more point: The app is not distributed via MDM. App will be distributed out side the app store. Questions: What is the correct way to programmatically install and trust a root certificate in the System keychain? Does this require additional entitlements, signing, or profile configurations? Is it possible outside of MDM management? Any guidance or working samples would be greatly appreciated.
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416
Jul ’25
Transfer an application between accounts with an existing App Group
Due to business requirements, we need to transfer our app Gem Space for iOS from our current Apple Developer account to a new account. We have a major concern regarding our users and the data associated with the app. The user data is currently stored using an App Group with the identifier, for example: "group.com.app.sharedData" According to some information we’ve found, it might be possible to complete the transfer by removing the App Group from the old account and creating a new one with the same identifier in the new account. However, other sources suggest that App Group containers are owned by the specific team, and data stored in the container may become inaccessible after the app is transferred to a different team. This raises concerns about the possibility of users losing access to their data after updating the app from the new account. Could you please clarify the expected behavior of App Groups in this case? Do we need to perform any kind of data migration, and if so, could you please provide detailed guidance on how to do it safely and without impacting user data access?
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102
Apr ’25
Downloading Developer ID provisioning profiles - missing new entitlements
Please provide a descriptive title for your feedback: Downloading Developer ID provisioning profiles - missing new entitlements Which area are you seeing an issue with? App Store Connect What type of feedback are you reporting? Incorrect/Unexpected Behavior Please provide the App name/App ID if possible: com.onexengineering.themedeck.macos Please describe the issue and what steps we can take to reproduce it bug in App Store Connect where downloading Developer ID provisioning profiles are missing the new entitlements regenerated from scratch -- App Store Connect says entitlements are good, but actual file confirms entitlements are missing App Store provisioning profiles seem to be unaffected (ignore my incorrect naming of files)
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350
Jul ’25
C++ HMAC-SHA256 Signature Works in Python, Fails in C++ — Possible Xcode Runtime Issue?
Hi all, I’m building a macOS-native C++ trading bot, compiled via Xcode. It sends REST API requests to a crypto exchange (Bitvavo) that require HMAC-SHA256 signatures using a pre-sign string (timestamp + method + path + body) and an API secret. Here’s the issue: • The exact same pre-sign string and API secret produce valid responses when signed using Python (hmac.new(secret, msg, hashlib.sha256)), • But when I generate the HMAC signature using C++ (HMAC(EVP_sha256, ...) via OpenSSL), the exchange returns an invalid signature error. Environment: • Xcode 15.3 / macOS 14.x • OpenSSL installed via Homebrew • HMAC test vectors match Python’s output for basic strings (so HMAC lib seems correct) Yet when using the real API keys and dynamic timestamped messages, something differs enough to break verification — possibly due to UTF-8 encoding, memory alignment, or newline handling differences in the Xcode C++ runtime? Has anyone experienced subtle differences between Python and C++ HMAC-SHA256 behavior when compiled in Xcode? I’ve published a GitHub repo for reproducibility: 🔗 https://github.com/vanBaardewijk/bitvavo-cpp-signature-test Thanks in advance for any suggestions or insights. Sascha
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786
Jul ’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.
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May ’25
Help with Entitlements for Keychain Access
Hi everyone, I’m working an Objective-C lib that performs Keychain operations, such as generating cryptographic keys and signing data. The lib will be used by my team in a Java program for macOS via JNI. When working with the traditional file-based Keychain (i.e., without access control flags), everything works smoothly, no issues at all. However, as soon as I try to generate a key using access control flags SecAccessControlCreateWithFlags, the Data Protection Keychain returns error -34018 (errSecMissingEntitlement) during SecKeyCreateRandomKey. This behavior is expected. To address this, I attempted to codesign my native dynamic library (.dylib) with an entitlement plist specifying various combinations of: keychain-access-groups com.apple.security.keychain etc. with: My Apple Development certificate Developer ID Application certificate Apple Distribution certificate None of these combinations made a difference, the error persists. I’d love to clarify: Is it supported to access Data Protection Keychain / Secure Enclave Keys in this type of use case? If so, what exact entitlements does macOS expect when calling SecKeyCreateRandomKey from a native library? I’d really appreciate any guidance or clarification. Thanks in advance! Best regards, Neil
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423
Jul ’25
TKTokenSession not used
Hi, I'm working on developing my own CryptoTokenKit (CTK) extension to enable codesign with HSM-backed keys. Here's what I’ve done so far: The container app sets up the tokenConfiguration with TKTokenKeychainCertificate and TKTokenKeychainKey. The extension registers successfully and is visible via pluginkit when launching the container app. The virtual smartcard appears when running security list-smartcards. The certificate, key, and identity are all visible using security export-smartcard -i [card]. However, nothing appears in the Keychain. After adding logging and reviewing output in the Console, I’ve observed the following behavior when running codesign: My TKTokenSession is instantiated correctly, using my custom TKToken implementation — so far, so good. However, none of the following TKTokenSession methods are ever called: func tokenSession(_ session: TKTokenSession, beginAuthFor operation: TKTokenOperation, constraint: Any) throws -> TKTokenAuthOperation func tokenSession(_ session: TKTokenSession, supports operation: TKTokenOperation, keyObjectID: TKToken.ObjectID, algorithm: TKTokenKeyAlgorithm) -> Bool func tokenSession(_ session: TKTokenSession, sign dataToSign: Data, keyObjectID: Any, algorithm: TKTokenKeyAlgorithm) throws -> Data func tokenSession(_ session: TKTokenSession, decrypt ciphertext: Data, keyObjectID: Any, algorithm: TKTokenKeyAlgorithm) throws -> Data func tokenSession(_ session: TKTokenSession, performKeyExchange otherPartyPublicKeyData: Data, keyObjectID objectID: Any, algorithm: TKTokenKeyAlgorithm, parameters: TKTokenKeyExchangeParameters) throws -> Data The only relevant Console log is: default 11:31:15.453969+0200 PersistentToken [0x154d04850] invalidated because the client process (pid 4899) either cancelled the connection or exited There’s no crash report related to the extension, so my assumption is that ctkd is closing the connection for some unknown reason. Is there any way to debug this further? Thank you for your help.
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Apr ’25
DCError.invalidInput on generateAssertion() - Affecting Small Subset of Users
Issue Summary I'm encountering a DCError.invalidInput error when calling DCAppAttestService.shared.generateAssertion() in my App Attest implementation. This issue affects only a small subset of users - the majority of users can successfully complete both attestation and assertion flows without any issues. According to Apple Engineer feedback, there might be a small implementation issue in my code. Key Observations Success Rate: ~95% of users complete the flow successfully Failure Pattern: The remaining ~5% consistently fail at assertion generation Key Length: Logs show key length of 44 characters for both successful and failing cases Consistency: Users who experience the error tend to experience it consistently Platform: Issue observed across different iOS versions and device types Environment iOS App Attest implementation Using DCAppAttestService for both attestation and assertion Custom relying party server communication Issue affects ~5% of users consistently Key Implementation Details 1. Attestation Flow (Working) The attestation process works correctly: // Generate key and attest (successful for all users) self.attestService.generateKey { keyId, keyIdError in guard keyIdError == nil, let keyId = keyId else { return completionHandler(.failure(.dcError(keyIdError as! DCError))) } // Note: keyId length is consistently 44 characters for both successful and failing users // Attest key with Apple servers self.attestKey(keyId, clientData: clientData) { result in // ... verification with RP server // Key is successfully stored for ALL users (including those who later fail at assertion) } } 2. Assertion Flow (Failing for ~5% of Users with invalidInput) The assertion generation fails for a consistent subset of users: // Get assertion data from RP server self.assertRelyingParty.getAssertionData(kid, with: data) { result in switch result { case .success(let receivedData): let session = receivedData.session let clientData = receivedData.clientData let hash = clientData.toSHA256() // SHA256 hash of client data // THIS CALL FAILS WITH invalidInput for ~5% of users // Same keyId (44 chars) that worked for attestation self.attestService.generateAssertion(kid, clientDataHash: hash) { assertion, err in guard err == nil, let assertion = assertion else { // Error: DCError.invalidInput if let err = err as? DCError, err.code == .invalidKey { return reattestAndAssert(.invalidKey, completionHandler) } else { return completionHandler(.failure(.dcError(err as! DCError))) } } // ... verification logic } } } 3. Client Data Structure Client data JSON structure (identical for successful and failing users): // For attestation (works for all users) let clientData = ["challenge": receivedData.challenge] // For assertion (fails for ~5% of users with same structure) var clientData = ["challenge": receivedData.challenge] if let data = data { // Additional data for assertion clientData["account"] = data["account"] clientData["amount"] = data["amount"] } 4. SHA256 Hash Implementation extension Data { public func toSHA256() -> Data { return Data(SHA256.hash(data: self)) } } 5. Key Storage Implementation Using UserDefaults for key storage (works consistently for all users): private let keyStorageTag = "app-attest-keyid" func setKey(_ keyId: String) -> Result<(), KeyStorageError> { UserDefaults.standard.set(keyId, forKey: keyStorageTag) return .success(()) } func getKey() -> Result<String?, KeyStorageError> { let keyId = UserDefaults.standard.string(forKey: keyStorageTag) return .success(keyId) } Questions User-Specific Factors: Since this affects only ~5% of users consistently, could there be device-specific, iOS version-specific, or account-specific factors that cause invalidInput? Key State Validation: Is there any way to validate the state of an attested key before calling generateAssertion()? The key length (44 chars) appears normal for both successful and failing cases. Keychain vs UserDefaults: Could the issue be related to using UserDefaults instead of Keychain for key storage? Though this works for 95% of users. Race Conditions: Could there be subtle race conditions or timing issues that only affect certain users/devices? Error Recovery: Is there a recommended way to handle this error? Should we attempt re-attestation for these users? Additional Context & Debugging Attempts Consistent Failure: Users who experience this error typically experience it on every attempt Key Validation: Both successful and failing users have identical key formats (44 character strings) Device Diversity: Issue observed across different device models and iOS versions Server Logs: Our server successfully provides challenges and processes attestation for all users Re-attestation: Forcing re-attestation sometimes resolves the issue temporarily, but it often recurs The fact that 95% of users succeed with identical code suggests there might be some environmental or device-specific factor that we're not accounting for. Any insights into what could cause invalidInput for a subset of users would be invaluable.
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Jun ’25
No MDM settings to control macOS pasteboard privacy?
For context, my company develops a data loss prevention (DLP) product. Part of our functionality is the ability to detect sensitive data being pasted into a web browser or cloud-based app. The AppKit release notes for April 2025 document an upcoming “macOS pasteboard privacy” feature, which will presumably ship in macOS 26. Using the user default setting “EnablePasteboardPrivacyDeveloperPreview” documented in the release notes, I tested our agent under macOS 15.5, and encountered a modal alert reading " is trying to access the pasteboard" almost immediately, when the program reads the General pasteboard to scan its contents. Since our product is aimed at enterprise customers (and not individual Mac users), I believed Apple would implement a privacy control setting for this new feature. This would allow our customers to push a configuration profile via MDM, with the “Paste from Other Apps” setting for our application preset to “Allow”, so that they can install our product on their endpoints without manual intervention. Unfortunately, as of macOS 26 beta 4 (25A5316i), there does not seem to be any such setting documented under Device Management — for example in PrivacyPreferencesPolicyControl.Services, which lists a number of similar settings. Without such a setting available, a valuable function of our product will be effectively crippled when macOS 26 is released. Is there such a setting (that I've overlooked)? If not, allow me to urge Apple to find the resources to implement one, so that our customers can preset “Paste from Other Apps” to “Allow” for our application.
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720
Jul ’25
ASWebAuthenticationSession + Universal Links Callback Issue
Problem Description: In our App, When we launch the web login part using ASWebAuthentication + Universal Links with callback scheme as "https", we are not receiving callback. Note: We are using "SwiftUIWebAuthentication" Swift Package Manager to display page in ASWebAuth. But when we use custom url scheme instead of Universal link, app able to receive call back every time. We use ".onOpenURL" to receive universal link callback scheme.
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Jul ’25
SFCertificateView Memory Leak
I've been spending days trying to solve the memory leak in a small menu bar application I've wrote (SC Menu). I've used Instruments which shows the leaks and memory graph which shows unreleased allocations. This occurs when someone views a certificate on the smartcard. Basically it opens a new window and displays the certificate, the same way Keychain Access displays a certificate. Whenever I create an SFCertificateView instance and set setDetailsDisclosed(true) - a memory leak happens. Instruments highlights that line. import Cocoa import SecurityInterface class ViewCertsViewController: NSViewController { var selectedCert: SecIdentity? = nil override func viewDidLoad() { super.viewDidLoad() self.view = NSView(frame: NSRect(x: 0, y: 0, width: 500, height: 500)) self.view.wantsLayer = true var secRef: SecCertificate? = nil guard let selectedCert else { return } let certRefErr = SecIdentityCopyCertificate(selectedCert, &secRef) if certRefErr != errSecSuccess { os_log("Error getting certificate from identity: %{public}@", log: OSLog.default, type: .error, String(describing: certRefErr)) return } let scrollView = NSScrollView() scrollView.translatesAutoresizingMaskIntoConstraints = false scrollView.borderType = .lineBorder scrollView.hasHorizontalScroller = true scrollView.hasVerticalScroller = true let certView = SFCertificateView() guard let secRef = secRef else { return } certView.setCertificate(secRef) certView.setDetailsDisclosed(true) certView.setDisplayTrust(true) certView.setEditableTrust(true) certView.setDisplayDetails(true) certView.setPolicies(SecPolicyCreateBasicX509()) certView.translatesAutoresizingMaskIntoConstraints = false scrollView.documentView = certView view.addSubview(scrollView) // Layout constraints NSLayoutConstraint.activate([ scrollView.leadingAnchor.constraint(equalTo: view.leadingAnchor), scrollView.trailingAnchor.constraint(equalTo: view.trailingAnchor), scrollView.topAnchor.constraint(equalTo: view.topAnchor), scrollView.bottomAnchor.constraint(equalTo: view.bottomAnchor), // Provide certificate view a width and height constraint certView.widthAnchor.constraint(equalTo: scrollView.widthAnchor), certView.heightAnchor.constraint(greaterThanOrEqualToConstant: 500) ]) } } https://github.com/boberito/sc_menu/blob/dev_2.0/smartcard_menu/ViewCertsViewController.swift Fairly simple.
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Oct ’25
Access Unix Socket from App Sandbox
Hello, I want to access the Docker socket API from inside the macOS App Sandbox. The method queries the API using curl with --unix-socket. However, the Sandbox blocks the request, as shown by the log: curl(22299) deny(1) network-outbound /Users/user/.docker/run/docker.sock Outgoing network traffic is generally allowed, but access to the Docker Unix socket is denied. Here’s the code I’m using: private func executeDockerAPI() -> String { let process = Process() let pipe = Pipe() process.executableURL = URL(fileURLWithPath: "/usr/bin/curl") process.arguments = [ "--unix-socket", "/Users/user/.docker/run/docker.sock", "http://127.0.0.1/containers/json" ] process.standardOutput = pipe process.standardError = pipe do { try process.run() process.waitUntilExit() let data = pipe.fileHandleForReading.readDataToEndOfFile() if let output = String(data: data, encoding: .utf8) { return output } else { return "Error while decoding" } } catch { return "Error running command: \(error.localizedDescription)" } } Is there any entitlement or sandbox configuration I’m missing to allow access to /Users/user/.docker/run/docker.sock from inside the sandbox?
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387
Jul ’25
ASWebAuthenticationSession password autofill iOS 18.5 broken
I have been implementing an sdk for authenticating a user. I have noticed that on iOS 18.5, whether using SFSafariViewController, or the sdk (built on ASWebAuthenticationSession), password autofill does not work. I have confirmed it works on a different device running iOS 18.0.1. Are there any work arounds for this at this time? Specifically for ASWebAuthenticationSession?
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262
Jul ’25
Launch Constraint, SIP and legacy launchd plist
I have 2 basic questions related to Launch Constraints: [Q1] Are Launch Constraints supposed to work when SIP is disabled? From what I'm observing, when SIP is disabled, Launch Constraints (e.g. Launch Constraint Parent Process) are not enforced. I can understand that. But it's a bit confusing considering that the stack diagram in the WWDC 2023 session is placing the 'Environment Constraints' block under SIP, not above. Also the documentation only mentions SIP for the 'is-sip-protected' fact. [Q2] Is the SpawnConstraint key in legacy launchd plist files (i.e. inside /Library/Launch(Agents|Daemons)) officially supported? From what I'm seeing, it seems to be working when SIP is enabled. But the WWDC session and the documentation don't really talk about this case.
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Jun ’25
How to Programmatically Install and Trust Root Certificate in System Keychain
I am developing a macOS application (targeting macOS 13 and later) that is non-sandboxed and needs to install and trust a root certificate by adding it to the System keychain programmatically. I’m fine with prompting the user for admin privileges or password, if needed. So far, I have attempted to execute the following command programmatically from both: A user-level process A root-level process sudo security add-trusted-cert -d -r trustRoot -k /Library/Keychains/System.keychain /path/to/cert.pem While the certificate does get installed, it does not appear as trusted in the Keychain Access app. One more point: The app is not distributed via MDM. App will be distributed out side the app store. Questions: What is the correct way to programmatically install and trust a root certificate in the System keychain? Does this require additional entitlements, signing, or profile configurations? Is it possible outside of MDM management? Any guidance or working samples would be greatly appreciated.
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3
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416
Activity
Jul ’25
Transfer an application between accounts with an existing App Group
Due to business requirements, we need to transfer our app Gem Space for iOS from our current Apple Developer account to a new account. We have a major concern regarding our users and the data associated with the app. The user data is currently stored using an App Group with the identifier, for example: "group.com.app.sharedData" According to some information we’ve found, it might be possible to complete the transfer by removing the App Group from the old account and creating a new one with the same identifier in the new account. However, other sources suggest that App Group containers are owned by the specific team, and data stored in the container may become inaccessible after the app is transferred to a different team. This raises concerns about the possibility of users losing access to their data after updating the app from the new account. Could you please clarify the expected behavior of App Groups in this case? Do we need to perform any kind of data migration, and if so, could you please provide detailed guidance on how to do it safely and without impacting user data access?
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2
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102
Activity
Apr ’25
How can I determine if an application is using an external device
For security reasons, my application needs to prohibit external devices. If it is determined that the current phone is connected to any external devices, including non MFI authenticated devices, the app will exit. Please tell me how to do it? Thanks for your help.
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1
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188
Activity
May ’25
Downloading Developer ID provisioning profiles - missing new entitlements
Please provide a descriptive title for your feedback: Downloading Developer ID provisioning profiles - missing new entitlements Which area are you seeing an issue with? App Store Connect What type of feedback are you reporting? Incorrect/Unexpected Behavior Please provide the App name/App ID if possible: com.onexengineering.themedeck.macos Please describe the issue and what steps we can take to reproduce it bug in App Store Connect where downloading Developer ID provisioning profiles are missing the new entitlements regenerated from scratch -- App Store Connect says entitlements are good, but actual file confirms entitlements are missing App Store provisioning profiles seem to be unaffected (ignore my incorrect naming of files)
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1
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350
Activity
Jul ’25
C++ HMAC-SHA256 Signature Works in Python, Fails in C++ — Possible Xcode Runtime Issue?
Hi all, I’m building a macOS-native C++ trading bot, compiled via Xcode. It sends REST API requests to a crypto exchange (Bitvavo) that require HMAC-SHA256 signatures using a pre-sign string (timestamp + method + path + body) and an API secret. Here’s the issue: • The exact same pre-sign string and API secret produce valid responses when signed using Python (hmac.new(secret, msg, hashlib.sha256)), • But when I generate the HMAC signature using C++ (HMAC(EVP_sha256, ...) via OpenSSL), the exchange returns an invalid signature error. Environment: • Xcode 15.3 / macOS 14.x • OpenSSL installed via Homebrew • HMAC test vectors match Python’s output for basic strings (so HMAC lib seems correct) Yet when using the real API keys and dynamic timestamped messages, something differs enough to break verification — possibly due to UTF-8 encoding, memory alignment, or newline handling differences in the Xcode C++ runtime? Has anyone experienced subtle differences between Python and C++ HMAC-SHA256 behavior when compiled in Xcode? I’ve published a GitHub repo for reproducibility: 🔗 https://github.com/vanBaardewijk/bitvavo-cpp-signature-test Thanks in advance for any suggestions or insights. Sascha
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2
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786
Activity
Jul ’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.
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4
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314
Activity
May ’25
Help with Entitlements for Keychain Access
Hi everyone, I’m working an Objective-C lib that performs Keychain operations, such as generating cryptographic keys and signing data. The lib will be used by my team in a Java program for macOS via JNI. When working with the traditional file-based Keychain (i.e., without access control flags), everything works smoothly, no issues at all. However, as soon as I try to generate a key using access control flags SecAccessControlCreateWithFlags, the Data Protection Keychain returns error -34018 (errSecMissingEntitlement) during SecKeyCreateRandomKey. This behavior is expected. To address this, I attempted to codesign my native dynamic library (.dylib) with an entitlement plist specifying various combinations of: keychain-access-groups com.apple.security.keychain etc. with: My Apple Development certificate Developer ID Application certificate Apple Distribution certificate None of these combinations made a difference, the error persists. I’d love to clarify: Is it supported to access Data Protection Keychain / Secure Enclave Keys in this type of use case? If so, what exact entitlements does macOS expect when calling SecKeyCreateRandomKey from a native library? I’d really appreciate any guidance or clarification. Thanks in advance! Best regards, Neil
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1
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423
Activity
Jul ’25
TKTokenSession not used
Hi, I'm working on developing my own CryptoTokenKit (CTK) extension to enable codesign with HSM-backed keys. Here's what I’ve done so far: The container app sets up the tokenConfiguration with TKTokenKeychainCertificate and TKTokenKeychainKey. The extension registers successfully and is visible via pluginkit when launching the container app. The virtual smartcard appears when running security list-smartcards. The certificate, key, and identity are all visible using security export-smartcard -i [card]. However, nothing appears in the Keychain. After adding logging and reviewing output in the Console, I’ve observed the following behavior when running codesign: My TKTokenSession is instantiated correctly, using my custom TKToken implementation — so far, so good. However, none of the following TKTokenSession methods are ever called: func tokenSession(_ session: TKTokenSession, beginAuthFor operation: TKTokenOperation, constraint: Any) throws -> TKTokenAuthOperation func tokenSession(_ session: TKTokenSession, supports operation: TKTokenOperation, keyObjectID: TKToken.ObjectID, algorithm: TKTokenKeyAlgorithm) -> Bool func tokenSession(_ session: TKTokenSession, sign dataToSign: Data, keyObjectID: Any, algorithm: TKTokenKeyAlgorithm) throws -> Data func tokenSession(_ session: TKTokenSession, decrypt ciphertext: Data, keyObjectID: Any, algorithm: TKTokenKeyAlgorithm) throws -> Data func tokenSession(_ session: TKTokenSession, performKeyExchange otherPartyPublicKeyData: Data, keyObjectID objectID: Any, algorithm: TKTokenKeyAlgorithm, parameters: TKTokenKeyExchangeParameters) throws -> Data The only relevant Console log is: default 11:31:15.453969+0200 PersistentToken [0x154d04850] invalidated because the client process (pid 4899) either cancelled the connection or exited There’s no crash report related to the extension, so my assumption is that ctkd is closing the connection for some unknown reason. Is there any way to debug this further? Thank you for your help.
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3
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152
Activity
Apr ’25
DCError.invalidInput on generateAssertion() - Affecting Small Subset of Users
Issue Summary I'm encountering a DCError.invalidInput error when calling DCAppAttestService.shared.generateAssertion() in my App Attest implementation. This issue affects only a small subset of users - the majority of users can successfully complete both attestation and assertion flows without any issues. According to Apple Engineer feedback, there might be a small implementation issue in my code. Key Observations Success Rate: ~95% of users complete the flow successfully Failure Pattern: The remaining ~5% consistently fail at assertion generation Key Length: Logs show key length of 44 characters for both successful and failing cases Consistency: Users who experience the error tend to experience it consistently Platform: Issue observed across different iOS versions and device types Environment iOS App Attest implementation Using DCAppAttestService for both attestation and assertion Custom relying party server communication Issue affects ~5% of users consistently Key Implementation Details 1. Attestation Flow (Working) The attestation process works correctly: // Generate key and attest (successful for all users) self.attestService.generateKey { keyId, keyIdError in guard keyIdError == nil, let keyId = keyId else { return completionHandler(.failure(.dcError(keyIdError as! DCError))) } // Note: keyId length is consistently 44 characters for both successful and failing users // Attest key with Apple servers self.attestKey(keyId, clientData: clientData) { result in // ... verification with RP server // Key is successfully stored for ALL users (including those who later fail at assertion) } } 2. Assertion Flow (Failing for ~5% of Users with invalidInput) The assertion generation fails for a consistent subset of users: // Get assertion data from RP server self.assertRelyingParty.getAssertionData(kid, with: data) { result in switch result { case .success(let receivedData): let session = receivedData.session let clientData = receivedData.clientData let hash = clientData.toSHA256() // SHA256 hash of client data // THIS CALL FAILS WITH invalidInput for ~5% of users // Same keyId (44 chars) that worked for attestation self.attestService.generateAssertion(kid, clientDataHash: hash) { assertion, err in guard err == nil, let assertion = assertion else { // Error: DCError.invalidInput if let err = err as? DCError, err.code == .invalidKey { return reattestAndAssert(.invalidKey, completionHandler) } else { return completionHandler(.failure(.dcError(err as! DCError))) } } // ... verification logic } } } 3. Client Data Structure Client data JSON structure (identical for successful and failing users): // For attestation (works for all users) let clientData = ["challenge": receivedData.challenge] // For assertion (fails for ~5% of users with same structure) var clientData = ["challenge": receivedData.challenge] if let data = data { // Additional data for assertion clientData["account"] = data["account"] clientData["amount"] = data["amount"] } 4. SHA256 Hash Implementation extension Data { public func toSHA256() -> Data { return Data(SHA256.hash(data: self)) } } 5. Key Storage Implementation Using UserDefaults for key storage (works consistently for all users): private let keyStorageTag = "app-attest-keyid" func setKey(_ keyId: String) -> Result<(), KeyStorageError> { UserDefaults.standard.set(keyId, forKey: keyStorageTag) return .success(()) } func getKey() -> Result<String?, KeyStorageError> { let keyId = UserDefaults.standard.string(forKey: keyStorageTag) return .success(keyId) } Questions User-Specific Factors: Since this affects only ~5% of users consistently, could there be device-specific, iOS version-specific, or account-specific factors that cause invalidInput? Key State Validation: Is there any way to validate the state of an attested key before calling generateAssertion()? The key length (44 chars) appears normal for both successful and failing cases. Keychain vs UserDefaults: Could the issue be related to using UserDefaults instead of Keychain for key storage? Though this works for 95% of users. Race Conditions: Could there be subtle race conditions or timing issues that only affect certain users/devices? Error Recovery: Is there a recommended way to handle this error? Should we attempt re-attestation for these users? Additional Context & Debugging Attempts Consistent Failure: Users who experience this error typically experience it on every attempt Key Validation: Both successful and failing users have identical key formats (44 character strings) Device Diversity: Issue observed across different device models and iOS versions Server Logs: Our server successfully provides challenges and processes attestation for all users Re-attestation: Forcing re-attestation sometimes resolves the issue temporarily, but it often recurs The fact that 95% of users succeed with identical code suggests there might be some environmental or device-specific factor that we're not accounting for. Any insights into what could cause invalidInput for a subset of users would be invaluable.
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