Hey Jay,
Since Keyboard Maestro only runs on macOS that's quite important...
Create a global stand-alone macro that uses the Activate a Specific Application action for TextEdit.
Put a notification in it to make sure it's working.
If that doesn't work then report back and post your macro.
How to Post Your Macro to the Forum
If you haven't read this it's worth a couple of minutes of your time.
Tip: How Do I Get The Best Answer in the Shortest Time?
If it does work then:
- Try switching Microsoft Word to another app, pausing and then switching it back again.
- Restart both the Keyboard Maestro Editor and the Keyboard Maestro Engine.
- Reboot your system.
We do see problems with app-connections from time to time and for various reasons, but they're not that common.
-Chris