Handle edge cases in retry

**Problem**
When working with models, 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 files, tests, or entry points are named. Start by locating the model retry handling and its current error paths, then identify the retry edge cases described by the existing behavior. Done should include more descriptive errors and coverage for the affected cases, but the issue does not define those cases precisely.

Written by the indexing model from the issue text.