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This is such a common problem with Teles - there's actually a bit of bent tin with barbs which are supposed to dig into the wood as the jack retaining nut is tightened. In practice, the bloody thing often comes adrift after a while and results in your experience. You can get it reinstalled but personally, I can recommend 2 courses of action. Either install an Electrosocket, which involves 2 woodscrews but is a neat and safe solution. Alternatively, if it is imperative to retain the vintage look, ditch the barbed clip and glue in the jack cup with an epoxy resin glue, reinstalling the jack when the glue has dried. Good luck.
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