@alberti82 That's right. The error indicates that the keychain has not been unlocked. For iOS devices, this means the phone is locked. In those cases, the decryption cannot happen because the device's keys are locked away to protect them from attacks. On iOS devices, you can store your keychain item with less security if you need the value to be available in an unlocked state. However, that vastly reduces the security you'll get out of the Keychain, so consider your usecase. To store your keys on iOS with less security (this may work for macOS as well, idk), you can use: kSecAttrAccessibleAfterFirstUnlock (https://developer.apple.com/documentation/security/ksecattraccessiblealways) This means the value is not available upon boot-up, but once unlocked once, it'll subsequently be available. This provides the minimum amount of protection you should be using.

@fpappledeveloper - I was able to resolve the issue and you are correct. When you open the web inspector it immediately resets logins (cookies?). I resolved the issue. Here's what I tried, sorry I didn't pin down exactly what fixed it: Resetting all experiments: Develop -> Experimental Features -> Reset all to defaults Re-enabling Safari -> Preferences -> Privacy -> enable "Prevent cross site tracking" + enable "Allow privacy-preserving measurements of ad effectiveness" (I suspect this is the issue but not sure) Disabling all content blockers on various websites (i don't think this does anything) Disabling Syncing Platform Authenticator Updating macOS from 12.4 to 12.5