I had difficulty getting my tablet to work as expected after upgrading from Stretch to Buster the other day.
The tablet was recognized, and I could configure it and test it in the gnome settings and everything worked there. However, when I tried to use other applications like Krita and Gimp the second cursor created would never properly grab or interact with the application.
After much searching, I eventually found a question on askubuntu which made me ask myself: am I using XWayland or Xorg? One of the responses elucidated that tablet support for X applications under XWayland is an upcoming feature.
To switch back, at least temporarily to Xorg, you can log out of your session, and when logging back in click the small gear after you select your user and from that dropdown choose something like: “GNOME with XOrg”.
I’m not sure if the system default changed without me thinking about it, or if I had changed it at some point in the past (I doubt that I did), but at least for me XWayland is the new default.