Mine has repeatedly pulled itself out while putting the headset on (folding down the hinge pulls the cable hook back, dragging the cable with it), and works fine once I push the connector back in, so this doesn’t appear to be guaranteed outcome (or maybe I’ve just been lucky).
That said, this is a rather amateurish design flaw on HP’s part. I now leave a significant amount of extra slack between the hook and the connector itself, which prevents these disconnects for me. But the cable slack will slowly work itself out over time, so I have to pull some extra cable through every day or so.