Handle edge cases in timeout

**Problem**
When working with helpers, 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 or test is named. Start by locating the timeout handling and helper error paths, then inspect existing tests for timeout behavior. Done means the relevant edge cases are covered and failures produce more descriptive error messages.

Written by the indexing model from the issue text.