I thought I would share a workaround with everyone. It has so far prevented this issue (knock on wood).
When I’m heading to bed and I plug my phone in, I wait to hear the chirp indicating the phone is charging. If I don’t hear an audible chirp, I check to make sure I have unmuted the phone. If it is not muted and still won’t chirp, I then check to make sure the sound isn’t manually set all the way down.
If I check both of these and it STILL won’t chirp, I turn the phone off and then back on and start again. Every time I’ve done this, the phone will chirp when plugged in during step 1, and I’ve not had the alarm fail on me since.
I should mention that I’ve had to restart the phone to get system audio working in this way perhaps 1 out of every 20 times (this is a huge guess - it’s happened, and more than once, but I wasn’t explicitly tracking the incidents). That’s about how often the alarm would fail me. I’ll also say that it hasn’t happened since upgrading to iOS 13, but I still do it every night because I have no reason to trust Apple on this one.
I’m confident that the times I had to restart are the times when the alarm would have failed me - if you’re still having the issue, try this out. Hope it helps!