I wish they would design those headphone jacks to mount to the case, thus none of the stress is placed on main body of the connector or the solder joints.
Beyond that, for headphones, if you have not tried the ones that seal really well and block ambient sound, you should try some of the new ones that are fully wireless and low profile, you can wear them within basic over the ear NRR30+ hearing protection, or even larger electronic earmuffs and just turn the ambient sound passthrough up a little higher, then wear the earbuds under it, and you will get an extra 3-5 dB of sound attenuation which is good when you are at the range.
Furthermore, most rifles above a ~.22 caliber, will be at over 160dB and need double protection anyway.
If you go to the range regularly, give the in-ear earbuds another try, and compare the experience and performance to the standard foam earplugs + over the ear electronic earmuffs. The good ones should give a similar amount of attenuation, but with the added benefit of you being able to listen to a podcast or audio book while trying to get that sub MOA grouping.