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I uploaded the Video to reddit so you can see what I mean
But basically, if I use the pencil tool and I zoom in the line size changes no matter if the Zoom size with stage is selected or not.
It does work but your brush is set to one pixel size; that's the absolute minimum size the classic brush can have. At that size it's only going to work at a 100% stage zoom or higher. If you zoom-out to less than a 100%, that one pixel brush can't go any smaller, it can't do sub-pixel sizes so that's why you see it get bigger despite having the "zoom with stage" box checked.
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first, you're using the classic brush, not the pencil.
second, the brush size scales (or not), not previous strokes.
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It does work but your brush is set to one pixel size; that's the absolute minimum size the classic brush can have. At that size it's only going to work at a 100% stage zoom or higher. If you zoom-out to less than a 100%, that one pixel brush can't go any smaller, it can't do sub-pixel sizes so that's why you see it get bigger despite having the "zoom with stage" box checked.