Hey, this is definitely getting really close. However, I think for this to work our phones would need to be connected to my Wireguard all the time, right?

Apprise is interesting. One of the many things it talks to might be what I’m looking for. I’ve seen multiple instances on the Internet of people using some kind of notification to trigger an automation software on the phone which actually sets the alarm. That might be the route to go.

Home Assistant is an interesting idea. I only learned about it recently but I know it’s hella dense and I feel like figuring out how to get it to do this one thing might be a huge task. I’ll keep it in mind though if nothing else pops up.

I’ve never been able to get a calendar to reliably trigger alarms :(