So this is a new issue that was not there as of last week. I plugged in my headphones to my work laptop (Dell Latitude E7470) and no sound is coming through even though all aspects of the PC seem to recognize it. Playback devices, Dell Audio, the like. So it's not the jack. I tested my headphones with my phone and they work fine. I changed a bunch of settings, including turning off the power management option in Dell Audio.
I then undocked my laptop and then bam, audio through the headphones. Docked it again and it was gone. No idea what could be causing this. Neither of my external displays have audio throughput.
Well, I rolled back the RealTek audio driver and it seemed to do the trick. I didn't catch the updated version's number so if you come across this question in the future because yours you have the same issue, I apologize. Try rolling back yours though.