After Effects Paint Brush tool cursor not changing

Hello, 

When I work in After Effects using the Brush Tool (not the Roto Brush Tool) I noticed that my cursor does not change to the circle of the brush size I am trying to use but remains the standard cursor. I have on occasion seen it switch but nothing seems to be triggering it and then it goes back to the regular cursor. 

I am working in the Layer and not the Comp (and can see the brush strokes being painted on), ensured Caps Lock is not on, tried resetting my preferences, resetting my workspace, and updating After Effects and so far to no avail. 

Thanks.