I've had this bug for the better part of a year and I'm totally up to date on all my drivers. I'm using a Surface Book Pro with Performance Base. Basically, After Effects registers my first tap with the stylus and ignores everything after that until I move the touchpad.
I've had this issue with every version of After Effects I've installed going back to 2014. I've cleared my preferences, installed the Wintab drivers, and installed the Surface Book Platform drivers. Anyone else had this issue? Anyone else fixed it?
Honestly, that sounds like an issue with your surface. Especially if it's been happening with every version.
If anyone comes across this post, I found my answer on Reddit.
I asked how to get to those since Windows doesn't have that option under Pen & Ink settings.
"i seriously don't even know how to get to those settings manually, it's "pen and touch", but when you type that they don't show up. I got there by typing "flicks" into the start menu, then you get the pen and touch settings window with the "flicks" tab. Go to Pen options, there you'll find the check box.
The windows settings are a MESS."
Now basic clicking works in After Effects, but Pen Pressure doesn't. Evidently, that's a bug either with the way the pen is seen by Adobe or how Microsoft is emulating a Wacom pen.