@davidcook, let's focus on making commands sync with your Raspberry Pi first.

Did you use these instructions when you setup your Raspberry Pi?

If you install the background service with this command:

/usr/share/triggercmdagent/app/src/installdaemon.sh

... it runs as root, and reads /root/.TRIGGERcmdData/commands.json, and it will only sync your background commands (ground = background) not foreground commands.

If you're editing your /home/pi/.TRIGGERcmdData/commands.json that could be the problem.

Please show me the output of this command: systemctl status triggercmdagent
I'd like to confirm it's running.

Also, do you see the your Raspberry Pi listed on your "Your Computers" page? If not, maybe it didn't create a computer because you're not subscribed. You can only have one computer if you're not subscribed.