@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.