Hello Apple Developer Community, I'm running macOS 27.2 on Apple Silicon with Python 3.13.17 installed from the official python.org installer. I am investigating an inconsistency in macOS code-signing and trust verification. What I have observed: In the normal graphical Terminal, code-signature checks for /usr/bin/true and the installed Python 3.13 executable succeed. In an earlier, different execution context, trust verification reported CSSMERR_TP_NOT_TRUSTED. The Mac's date and time are configured automatically. The exact cause of the difference between execution contexts remains unknown. My questions: What could cause macOS trust evaluation to differ between execution contexts? Which read-only diagnostics could identify the cause? How can I investigate this without modifying Keychain trust settings, disabling system security or purchasing a paid developer membership? I can provide sanitized diagnostic logs if needed. Thank you for your help!