Handle edge cases in timeout

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

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

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

The issue names no files, tests, or entry points. Start by locating timeout and validation handling in the CLI, reproduce the reported edge cases, and inspect existing error-message tests if present; done means validation failures produce detailed, useful messages without breaking timeout behavior.

Written by the indexing model from the issue text.