Alright, the washer on the output jack on my strat has come loose multiple times this month. Every time I just tighten it by hand and it's fine, but I'm getting somewhat worried as I've never seen or heard of this before. Is it a common problem, or should I get a replacement output cable or use clay or something like that to stabilize it a la Red Special's pickups, or something? I use livewire cables if that means anything.

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My old Squire Strat did that all the time, i just took a pair of pliers and tightened it, and it stayed that way.
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Yeah, I tightened mine with a pair of pliers (little bit of cloth around them to make sure not to mess the surface of the guitar/jack up.) But it still comes loose from time to time, not much to worry about as far as I've noticed.