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Which FOSS smartwarch would you recommend?
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It might be possible to do that, but the Pinetime can only use Bluetooth, so you'd need to write something for both the Pinetime and the device is connected to.
Yeah, I was imagining that it was connected to my phone, but I'm not sure how to setup my phone such that it responds to messages like that - I've never tried sending my phone bluetooth messages and I don't know if that would be possible (to go watch to phone via BT and phone to self-hosted server via mobile network). Can I have an app always listening for messages over BT? Hopefully I don't need a PiZero W in my pocket: watch to Pi via BT as a relay, Pi to phone via Wifi hotspot, and phone to self-hosted server via mobile network. Sounds like a lot of work, lol. I'll think about applications for it. They'd have to be pretty awesome.
There are applications that can talk to the Pinetime, maybe you can modify one of them to understand a custom Bluetooth message?