Strange High E String Failure Mode

I've heard it said of tremolo use and Kahlers in particular, that guitar string windings at the ball end should be soldered.  I always wondered what the heck that was about.  From what I have discerned, Kahlers have fixed saddles and wrap the string ball ends around a semi-circular rotating stop, similar to Bigsby tremolos and, in a way, to some wrap-around TOM (Tune-O-Matic) fixed bridges.  And there, I thought, was the crux:  something about turning a corner with the wrapped end perhaps caused problems.

Now maybe I understand.

I lost the ability to maintain tuning on my high E string on my new homemade guitar.  Every time I did a bend, it came back low - and it's a fixed bridge.  It happened over and over and over.  I even loosed the Steinberger gearless tuner at the headstock, unclamped the string, grabbed the free tail and reclamped it with the slack taken up.  It kept happening.  Here were my theories, in descending order of probability:

1. string clamp mechanism slipping - but I didn't see any less tag end than I remembered having after the initial string installation
2. string stretching like all getout - but I couldn't imagine a string stretching that much without breaking
3. tuner shifting in the soft basswood of the tuner hole - but i saw no visual indication of it
4. adjustable saddle moving of its own accord - but I checked the compensation screw head and it was against the rear of the bridge
5. bridge moving - but the other strings were great

Then I measure the wrapping at the ball end where it comes through the rear of the bridge.  I measured 19/64ths, worked the string by bouncing the guitar on it repeatedly.  I measured 16/64ths, but I didn't believe it.  I stretched the string again and it became clear:  the high E string was getting pulled around the ball end and  smooshing the wrap toward the ball end.  In this picture you can see it:

Imagine for a moment that I had a camera made after about 2003, that could take a picture worth a damn.  You would see that the green arrow is approximately where the final wrap used to be, and the yellow arrow is where it is now.  Between the two is kinked-up string, unwrapped wraps that have wriggled out of the wrap zone.

From now on I will solder my strings, I guess.