... a couple weeks back, and I've decided that I want to use .10s on it.

So i got a couple of packs of 10s, but when I tried to put the high E on, it kept breaking.

Does anyone have any tips for restringing this?

I've put a kink in the wire before insterting the ball end, to keep the string in. Is this helping?
kinking is not helping. tune up slowly, stretching the string longitudinally as you do. tune a semitone or two flat first.
'59 Bassman Reissue
Custom Strat
Custom McCarty
Custom OM
Big Muff Pi
Dunlop Wah
Ah, I was told that kinking the string kept the ballend in without forcing it. I figured that it was not good for the very thin string life.

Slow tuning though, that's a plan.
Kinking the ball end of the string is what you do, its not that.

Unless you wiggle it back and forth and weaken the string, but I doubt you do. Check there aren't any sharp edges on the nut or saddle.
Ah, I was kinking about a centimetre up where the actual string starts, and bending it quite far.

Acoustics are harder than floyd roses to restring!

Thanks guys.
find out whereabouts the string is snapping, if its snapping at the bridge or nut then theres probably a sharp edge on them,
It's under the bridge, but I think that when I'm kinking the string it's making a little spiral shape. That's where it snapped from previously.