Improve error messages in middleware

**Description**
Currently helpers lacks proper monitoring support.

**Proposed solution**
Add configurable monitoring with sensible defaults.

**Priority**: Low/Medium

Start by locating the middleware and helper implementations, then inspect how errors are currently reported and whether monitoring hooks already exist. Done means the issue’s error messages are improved and monitoring is configurable with sensible defaults, but the issue does not name specific files or tests.

Written by the indexing model from the issue text.