Dell 5411 | Can't hear sound from audio jack

Hi, 

I'm utilizing a Dell Latitude 5411 machine and for a long time now, I'm struggling with an audio issue.

When I'm connecting a headset/set of speakers (several sets) to the 3.5mm audio jack - I can't hear anything. 

It's being picked up by the OS and I can see the audio device playing sound but it's not going through. I went over countless of Dell/youtube videos on troubleshooting audio things and I didn't get anyway with it. 

I'm adding some screenshots that will give away some of my OS details.