Symptom:

Are you seeing a "Bedtime wasn’t applied” in Parent mode or noticed your child’s using their device past the scheduled screen time?

Things to check:

Internet Connection

Apple devices require an active internet connection (cellular and/or Wi-Fi) at all times in order to apply changes to the schedule, refresh location and other changes. Here are a few areas to review:

1. Did your child’s device have poor reception at the time of the command or expected change in schedule?
2. Was the device turned off or in Airplane mode at the time of the scheduled screen time change?
3. Was the battery drained when your child’s device was supposed to have the scheduled screen time enabled?

Test Now:

1. Check that your child's device is connected to the internet.
2. From your parent mode, can you invoke the Time-Out command to block and hide the apps? If yes, then all is good and most likely it was just one of the three reasons ago.

Child tampering

Boomerang installs a Device Profile on your child’s iOS device. This is what applies our restrictions and screen time schedules. If removed, it will no longer allow you to control their device.

• On your child’s device, go to Settings > General > Device Profile (scroll down). Is Boomerang Device Profile still there?
• If yes, then all is good.
• If no, you can force a reinstall by opening the Boomerang app on your child’s device and it should prompt to reinstall the Device Profile.

Expired Certificate

If you installed Boomerang prior to September 2017, the certificate has expired.  Please uninstall Boomerang's Device Management Profile and also uninstall the Boomerang App than then reinstall Boomerang fresh.

Related: Why are some apps still available during Bedtime?