Legacy app protected by app proxy bypasses expected Conditional Access policy

Scenario

Legacy app protected by app proxy bypasses expected Conditional Access policy. The issue is affecting normal operations and needs a repeatable troubleshooting path that fits the MSP Toolkit style.

Recommended Resolution Path

1. Confirm the problem scope, affected users, and whether the issue is isolated to conditional access or part of a broader change.
2. Compare one known-good path against the failing path before making disruptive changes to the conditional access workflow.
3. Review recent updates, policy changes, cached credentials, or infrastructure dependencies that align with the first reported failure.
4. Apply the least disruptive corrective action first, then validate from the user perspective and document the root cause plus prevention notes.

Technician Notes

Confirm the result, document the root cause, and record any preventative action worth standardizing.