Improve error messages in middleware

**Problem**
When working with hooks, 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 identified in the issue. Start by locating the middleware hook error paths, then determine which failures currently produce unhelpful messages. Done means the relevant hook errors provide more descriptive debugging context and the changed behavior is covered by the project's existing checks.

Written by the indexing model from the issue text.