Improve error messages in utils

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

**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 the authentication flow and configuration handling, then trace where failed authentication requests are surfaced. Done means an `enable_retry` option defaults to false and authentication retry behavior is covered by the relevant tests.

Written by the indexing model from the issue text.