Headphone not detected? topic

Weird thing started happening to my phone: when I plug in a pair of headphones (with or without mic) the phone does not detect that they are plugged in! Sound always comes out of the speakers. I've used apps like SoundAbout to force sound of the headset jack and it seems to do the trick. But as you know, this just spoofs the phone... it still thinks it's using the speakers so you'll lose mic capabilities.

The odd thing is that if I turn off my phone, plug in a pair of headphones, and then continue to turn my phone back on... once booted the phone will recognize that it has a pair of headphones plugged in and everything will be fine. Won't work when I unplug and try to replug. It only detects the headphones on boot.

1) Is there a solution to this?
2) Anyone know how the mechanics of this works? It seems like on boot it always tries to check if there are headphones... but something mechanical in the headphone jack triggers the check after boot (may mean I have a mechanical failure)?
3) Is there a way to force headphone mode, more so than what Soundabout does? It's a pain to lose the mic, I use it a lot.

Here are other pertinents:
- Running newest SkyDragon Lollipop GPE rom with Sense Firmware... don't think it's the rom because it worked just last week
- Only recently started happening, not sure what could have caused it
- Noticed the phone always tries to update HTC Service pack, I think I fixed that issue
- Have yet to try cleaning, need to get rubbing alcohol

Thanks for any help anyone can provide me.