If scheduled maintenance doesn't happen (user closes the computer, workflow fails, etc.) and the policy is still failing, there won't be another attempt at a maintenance window until the next month.
Potential solutions
Schedule new maintenance windows sooner if device is still failing the same policy after a maintenance window
Problem
If scheduled maintenance doesn't happen (user closes the computer, workflow fails, etc.) and the policy is still failing, there won't be another attempt at a maintenance window until the next month.
Potential solutions