Overview
We are investigating repeated "login" Keychain prompts affecting our macOS application on macOS 26.6.x.
The issue appears after upgrading an existing installation. A clean uninstall/reinstall of the same version resolves it.
Changing the affected Keychain item's Access Control from "Confirm before allowing access" to explicitly allowing our application/process also stops the prompts.
On one affected machine, Apple Support observed a securityd crash followed by:
SecKeyCreateSignature failed
CSSMERR_DL_INVALID_DB_HANDLE
Our code uses some legacy SecKeychain* APIs, so we are currently investigating whether this is related.
Questions
Were there any changes in macOS 26.6.x around securityd, Keychain ACL handling, or legacy SecKeychain* APIs that could explain this?
Could an existing Keychain ACL become stale after an application upgrade, even when both versions are signed with the same Developer ID?
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