Handle edge cases in logging

**Problem**
When working with auth, the error messages could be more descriptive.

**Suggestion**
Improve error handling and add detailed error messages.

**Context**
This would help with debugging and maintenance.

Start by locating the authentication-related logging and error-handling paths in the repository. Identify the relevant edge cases and define the expected descriptive messages before changing behavior; done means the auth errors provide more useful debugging context and the affected checks pass.

Written by the indexing model from the issue text.