Or just build an automated tool that watches it. That's not too hard- I've done it in Python under Linux before: gitter <-> IRC <-> Discord It wasn't very difficult- you just need to do something like a keep-alive ping (which can be hidden in an invisible Discord channel) if you're having problems with your bridge.

That's what I meant with "constantly monitoring". If for some reason it fails you need someone to fix it, maybe it's not fixable due to changes from either provider ...

All that makes using bridges unreliable as you don't know if your messages was received by the other end.