Bit of a delay, there, while my iPad failed, was returned, and (eventually) replaced. I can now answer my own question for any future readers of the thread and confirm that: Mobile Safari on the iPad does not support Apple Pencil (or finger-based) drawing using the Freehand tool in roll20. Indeed, there are numerous problems with the site in Safari, which I will not enumerate here as I know it's not supported. Chrome for iPad behaves identically to Safari. As I wrote above, this is not surprising, as they share a rendering engine and JavaScript implementation. From roll20's perspective, they are more or less the same browser. Duet Display Pro for iPad (connected to, and driven by, a Windows PC) does not allow Freehand drawing either, with either Apple Pencil or finger. You can drag a Chrome (v81.0.4044.138) window over to the iPad's screen fine, and you can select tools from roll20's toolbar with the Apple Pencil, but touching the screen with either Pencil or finger doesn't cause roll20 to map any drawing events. So you cannot do freehand sketching. Firefox (v76.0.1) behaves the same way as Chrome does. Apple Pencil can be used within the roll20 UI but it can't be used to draw anything. Frustrating, but not exactly surprising. I haven't yet tried Apple's Sidecar implementation. That doesn't work well for me as my MacBook can't drive my main monitor and the iPad at full resolution at the same time, so it's not a setup I would use anyway. However I may try it out of interest. If I get around to it I'll post results here.