There's probably a mechanism preventing the headrest from being removed completely. This is likely because without the headrests in place, the vehicle does not meet its crash test standards. This is quite common today in new vehicles (at least in the U.S., where we can't be trusted to not put ourselves in harms way and then turn around and sue people for our own doings). See if this video helps you.

EDIT: if that method doesn't work, try the one below. I think the first video will do it for you, as that's how front headrests on other VW models currently on sale work (e.g., Tiguan, Atlas).

 

I was reading through the digital version of the U.S. owner's manual and came across this:

 

Tried this. Still didn't work. Took it to VW sand tech couldn't get it off. Oh well.

 

Are there little pin holes in the collars that the headrest posts are inserted into? If there are, try inserting a paper clip into the holes and see if a metal pin pops out. Some manufacturers use this method to prevent the headrests from being removed. I don’t have my ID.4 yet so I can’t take a look myself.

 

I didn't see any but I'll check again.

 

I was also trying to remove the headrest and had trouble at first. Unfortunately the videos are not the correct way to remove this style of head rest.
In the manual on page 91 is the correct way, but it was difficult to figure out.
I found the easiest way was to sit in the back seat, lower the headrest all the way to the bottom, then with your left hand push down and hold on the plastic ring and with your right hand push the headrest up towards the roof. The first position clicks which was throwing me off, but it will come out after that. Hope this helps.

 

Thank you. I'll try that.

 

This is a quick little video showing how.

 

I can't believe it! I tried unsuccessfully several times when I first got my 1st Edition because VW made a slim garbage bag with attachment holes that needed the seat headrest off. Went to my VW dealer and the VW tech couldn't do it either. I just watched your video and immediately went out to my car to try it. Two failed attemps, thinking...that guy doesn't know what he talking about . Tried one more time and "EUREKA!"...it worked. I had to use a great deal of force pushing up to get it out but it did finally release. Thank you so much!

 

Has anyone tried the passenger side? Is it the same? I cant get either of them off no matter how much force I put into it and I am a strong person.

 

I put it all the way down, then pushed down on the left plastic ring and with my right hand pushed up really hard and it finally popped off. Several previous attempts failed, even the VW tech failed and then a miracle happened on my last attempt and it came off.

 

Can anyone confirm that this is the same way to remove the headrest on the '23s? I tried what the manual and the video on this thread show several times yesterday and today with no luck. I haven't resorted to getting a 2nd person to help yet, but it really doesn't seem to want to budge. Any other tips or tricks would be appreciated.

 

My id4 worked exactly like in these posts, but headrest in my Amarok had a small spring loaded button under the round fitting. In both cars the headrests look exactly same on the outside.