> I was thinking about this because I think I've bumped into this before... So, I don't think it's a bug. If it is a bug, it's always existed... I think.

Either way, the issue seems to be that `Angle jitter` on a brush does weird things to anti-aliasing. Occasionally anti-aliasing disappears completely and generally just looks terrible. 

I had a moment of clarity and I realized that if I start with a rectangle with straight angles, the brush engine <sup><sub>(or whatever)</sub></sup> has to figure out the anti-aliasing and it seems like it is pretty much botching it. So I got an idea... what if you start with anti-aliasing?

I rotated my square 45 degrees before making it a brush and that seems to have given me a pretty good result. The straight angle square looks terrible in comparison.

>I also tested a blurred square with smaller brush size and that seemed to work better than no anti-aliasing, but it still failed quite badly in smaller sizes.

After that it occurred to me that in the bottom right result, **the anti-aliasing looks pretty damn good on the inside in every single square**.

When you make a brush, all whitespace gets trimmed out, so when I added some padding to the outside of the source image using a thick outside stroke with 1% opacity, the angle jittered result also looks pretty good.

What that leads me to believe is that when you make the brush, there is a square area surrounding the brush and that area is somehow cropping away part of the outer edge, when `angle jitter` rotates the brush. I'm not sure if cropping is actually what is happening, but it definitely seems like the outer edge is getting chipped off.

**So it's probably not that much to do about anti-aliasing after all, but rather when the square is rotated 45 degrees before making it a brush, the sides are as far away from the sides and nothing gets cropped when the brush is rotated using `angle jitter`.**

With 100% zoom:

[![enter image description here][1]][1]


  [1]: https://i.sstatic.net/SetSP.png