Improve error messages in utils

**Problem**
When working with middleware, 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 utils and middleware code paths mentioned in the issue, then read their existing error-handling behavior and current messages. Determine which middleware failures need clearer context and define completion by consistent, more descriptive errors that improve debugging.

Written by the indexing model from the issue text.