Headphone jacks have often been the bane of my existence. If you work in radio, you’ll know how often the plug shorts out, rendering your headphones useless. If you use ‘phones for portable devices with the little 1/8 plugs, you’re aware of how often that thing is the failure point.
And even if your plugs are in working order, the constant stress of plugging and and unplugging causes havoc on the plug itself. That can fail, too, rendering your device almost completely useless.
Time to find something better than the male-female plug-to-jack relationship. Phase ’em out. And here’s a great place to start.