After either latest upgrade to Monterey 12.6 or having installed the azure command line tools from brew I am having issues with my .NET application when it attempts to use the keychain for signing data: lientCertificateCredential authentication failed: The operation couldn’t be completed. (OSStatus error -25293 - CSSM Exception: -2147416032 CSSMERR_CSP_OPERATION_AUTH_DENIED) ---> Interop+AppleCrypto+AppleCFErrorCryptographicException: The operation couldn’t be completed. (OSStatus error -25293 - CSSM Exception: -2147416032 CSSMERR_CSP_OPERATION_AUTH_DENIED) at Interop.AppleCrypto.NativeCreateSignature(SafeSecKeyRefHandle privateKey, ReadOnlySpan`1 dataHash, PAL_HashAlgorithm hashAlgorithm, PAL_SignatureAlgorithm signatureAlgorithm) at Interop.AppleCrypto.CreateSignature(SafeSecKeyRefHandle privateKey, ReadOnlySpan`1 dataHash, PAL_HashAlgorithm hashAlgorithm, PAL_SignatureAlgorithm signatureAlgorithm) at System.Security.Cryptography.RSAImplementation.RSASecurityTransforms.SignHash(Byte[] hash, HashAlgorithmName hashAlgorithm, RSASignaturePadding padding) at System.Security.Cryptography.RSA.SignData(Byte[] data, Int32 offset, Int32 count, HashAlgorithmName hashAlgorithm, RSASignaturePadding padding) I post this here because the core of the exception appears to be an exceptional access pattern that results in the following failure code: OSStatus error -25293 - CSSM Exception: -2147416032 CSSMERR_CSP_OPERATION_AUTH_DENIED Unfortunately I haven't found much about this on the internet. I created an issue with the relevant dotnet repo,, but feel that it may make sense to follow this up here. My current (very tedious)workaround is to restart the machine - a re-login doesn't help, but a reboot makes this work as it previously did after which, somehow, the exception resurfaces again after some time (as if something expires?)