Handle edge cases in caching

**Feature request**
It would be great to have retry for hooks.

**Use case**
Many users need this functionality for production deployments.

**Implementation idea**
Add a new config option `enable_retry` with default `false`.

No files, tests, or entry points are named. Start by locating hook handling and configuration parsing, then trace how hook failures are reported. Done means an enable_retry option defaults to false and, when enabled, retries hooks according to behavior clarified by the maintainers.

Written by the indexing model from the issue text.