In the first few months that I owned the X1A, I changed headphones roughly twice a day, going from over-ears at work to in-ears at home. The jack felt steadily looser with time--not putting up much of a fight when inserting or removing the cable plug. That had me worried. That's when I bought a short extension to leave plugged in at all times.
Then one day I lost a channel. When I unplugged my headphones to try another pair, the outer gold ring was visibly loose. I hadn't noticed any looseness with it before, but it was now barely holding onto the unit.
These two problems (the jack not holding the plug tightly and the ring falling off) seem unrelated: the gold ring is not involved in "grasping" the plug.
At any rate, I no longer insert/remove the plug from the X1A and it's shielded from anything pushing on it. Routing the wire out the side makes it harder for tension on the cable to pull on the plug itself. Not aesthetically pleasing. And my nice cables now end up going through six inches of who-knows-what kind of wire. If I could find a nice right-angle extension, I'd switch, but all the "audiophile" extensions I've found have straight plugs.
I could use a straight plug and make the ABS extend further from the top of the X1A. In that case, I think it would make more sense to route the cable out the top of the guard. Perhaps wrapping it around somehow, so cable tension can't make it to the plug.