Solved Headphone Jack only works if headphones are plugged in before starting Laptop

Hey! So I have a very niche problem. My headphone jack only works when I have my headphones already plugged in at the time of starting my laptop. This hasn't really been that much of an issue but sometimes I accidentally pull them out and then the only way to listen to audio through my headphones is by restarting my laptop.
Again, I've been doing that for literally months now so I didn't care thaaaat much. However, I got into video editing lately and want to record a voice over for a video but only have one jack for headphones or a microphone. Now my problem is that I can only record with the mic if it's already plugged in when I start the laptop but then to listen to the audio on my headphones (which I prefer because it's way cleaner and nicer) I would have to restart it again. And then do that everytime.
Now I really want to find out what the issue is exactly since it's been frustrating me for a while.
I deinstalled and reinstalled my audio driver multiple times but it still doesn't work.
I know nothing's wrong with my headphones because they work otherwise and they also do work with my laptop if plugged in before I turn it on. So it couldn't be the driver anyway I guess.
I really don't know what to do I searched for this for a long time now and am just really frustrated. I would really appreciate any tips! Thanks in advance!
I'm using a Dell XPS15 with Windows10

Hello! Yes I do!
Any idea helps!

JBL live 500 BT but I only got the headphones recently (Christmas) and I've had the headphone jack problem since months before that :/
speakers work fine.
My headphones also work fine when I've plugged them in before I turn on my laptop. But once it's on, and I accidentally pull out the headphone cable it won't work again, only if I turn it off, plug in my headphones and turn it on again, will I be able to listen to stuff on my headphones.

yes other headphones work.
I'm using a laptop so I have integrated speakers
I can connect via Bluetooth but the connection is chippy sometimes so I prefer the cord
Yes it's inserted correctly.

I did that already too :/
And as I said, it does work whenever I've plugged them in at the time of starting my laptop.

Yes, I really checked that it was inserted correctly, unplugged them and plugged them back in multiple times :/
But I do trust myself to plug them in correctly since it does work whenever I start my laptop

Dell XPS 15 9560
Well I tried but they make it really hard to contact them. Because I don't have a guarantee anymore, I'd have to pay to call them and they won't give out other information as to how else to contact them :/

But thank you anyways! I guess I'll just continue to live with the issue