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Whenever I get a guitar in my shop that has a jack problem, the first thing I do is pull the cheap -- and next to useless -- metric import jack, toss into the trash, then install a Switchcraft with a 3/8" inside diameter inside tooth lock washer (I buy them in boxes of 100), and voilà, no more jack issues, no more broken connections at the jack (unless there's a loose pot -- put lock washers on those, too).
I've worked on 50+ years old guitars that have a Switchcraft and lock washer. Unless someone in the past loosened the nut, it's almost like it was welded onto the jack.