I've managed to find a few great right angled cables that fit my Teles only to discover they won't fit the build with the electrosocket. One of my Danocasters has a shallower jack cub and it'll accept any plug I throw at it.. all I need is a source for that besides the one Mark Rutter has which I'm sure is great but I've got more than a dozen Teles that I would like to convert.
I've found this annoying problem too, and usually manage to make it work by not using a washer between the jack and socket, and sometimes have to countersink the back of the electrosocket if the jack doesn't screw in all the way flush.
The pencil might be easy to find at a gig if you have a socket in your bag, (just ask the nearest person texting on their i phone) or a chopstick if you're playing Chinese.
I can't bring myself to buy plastic guitar tools, but those nice deep offset box end wrenches work better than a socket with vice grips.
If needed, I go under the control plate to start and stick a screwdriver in the jack to hold the nut when tightening.
If you get the prong in the right spot you can tighten all the way.
If not it just keeps getting loose IME.
I think of the Tele jack cup prong arrangement as Leos one bad idea in a long brilliant career.
When they get loose they get replaced.