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You deserve a break

The break control panel (with progress bar and buttons) doesn't appear during a break

I've had a few other multi-monitor people report this. It seems like an issue that started with Catalina. Time Out should display the control panel on an available screen (you can choose which to use in the preferences), but on Catalina it seems to either think disconnected screens are still there, or isn't adjusting the position correctly, or something.

A workaround that has been successful for others is to Trash the break preferences: copy the following path and use the Finder's Go to Folder command to reveal it, then send it to the Trash:

~/Library/Containers/6Z7QW53WB6.com.dejal.timeout.free.break

Alternatively, you can use this Terminal command:

defaults delete 6Z7QW53WB6.com.dejal.timeout.free.break

That's for the Mac App Store edition; if you downloaded the app from the Dejal website, you can instead use this command:

defaults delete 6Z7QW53WB6.com.dejal.timeout.break

That won't affect any of your settings, but will reset the position of the control panel during the next break.