Handle edge cases in retry

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

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

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

No file, test, or entry point is named. Start by locating the utils retry implementation and its existing error handling, then identify the retry edge cases and expected descriptive messages. Done means the relevant failures produce clearer errors and coverage exists for the affected cases.

Written by the indexing model from the issue text.