If no break appears when you manually start one, or as scheduled, there are a few possibilities.

1. Firstly, look in the sidebar; it should indicate why a break didn’t occur.
2. You should restart your Mac. That often fixes wackiness.
3. If that doesn’t help, make sure you don’t have more than one copy of Time Out.
4. If still no luck, there may be a permissions issue.

To fix a permissions issue, try this:

Make sure Time Out is in your Applications folder.

Paste the following command into Terminal:

xattr -d -r -s com.apple.quarantine /Applications/Time\ Out.app

If this gives a permissions error (e.g. “xattr: [Errno 13] Permission denied”), try it again with sudo before the command, to elevate the privileges. You’ll need to enter your Administrator password. This command is safe to use with sudo:

sudo xattr -d -r -s com.apple.quarantine /Applications/Time\ Out.app