Given that I tend to overthink things which is a cause of my anxiety issue, I dread bringing the high E up to pitch when I put on fresh strings.
I know it's weird, but the anxiety of it possibly happening is enough to ruin the activity for me.
The High E does seem like the most over-stressed of all the strings!
Fortunately, I use good strings that almost never break. I also constantly bend the E string up 2 steps as I bring it up to pitch. It's ridiculous really, but it seems like I'm proving to myself that everything is perfectly okay by my performing a "normal" string bend up to the pitch that I'm ultimately going to tune the string to, to sort of prove to myself that it will be fine.