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Dean wrote: ↑12 Mar 2021, 16:45 Hello David, Matthieu is currently using version 6.3.42-1 of the driver

Thank you. I have Wacom Driver 6.3.40-2 . After backing up my settings I tried installing driver version 6.3.42-1, but it is incompatible with MacOS Mojave or Cintiq 21UX 2 (DTK-2100), which is what I have . So I am back to driver 6.3.40-2 . I may experiment with installing a few older drivers to see if there is any difference (on the chance that maybe the problem is only with driver 6.3.40-2 ?). Or maybe I need to bite the bullet and update to Big Sur ? What's the situation now with TVPaint running on Big Sur ? Have the issues been resolved ?

If Jeremy can't find anything in the source code that shows why the Flip Manual shortcut might not be working when triggered from the Wacom Express Key , I think I may give up on
using the Wacom Cintiq Express Keys and I'll find another type of programmable keypad like Butterstick mentioned by schwarzgrau or a Contour Shuttle Pro . (although I am hesitant to spend the money on yet another device , if I can possibly get the Wacom Express Keys to work properly to trigger the Flip Manual -- and what if those devices also don't work to trigger Flip Manual ? -- so I hold out hope that you can find a solution.)

Despite being a keyboard afficionado, I am not very familiar with detached keypads. Jérémy was absent for the last couple days but Xavier will be back next week so maybe we can find new leads.

D.T. Nethery wrote: ↑12 Mar 2021, 17:32

Dean wrote: ↑12 Mar 2021, 16:45 Hello David, Matthieu is currently using version 6.3.42-1 of the driver

Thank you. I have Wacom Driver 6.3.40-2 . After backing up my settings I tried installing driver version 6.3.42-1, but it is incompatible with MacOS Mojave or Cintiq 21UX 2 (DTK-2100), which is what I have . So I am back to driver 6.3.40-2 . I may experiment with installing a few older drivers to see if there is any difference (on the chance that maybe the problem is only with driver 6.3.40-2 ?).

UPDATE: here is the ANSWER to the problem. It is an issue with driver 6.3.40-2.
I went back to read the release notes on the Wacom support site and here is what I found:

When activating a keystroke assigned to a button (holding down an ExpressKey or pen button assigned to activate the Option key, for example), the keystroke improperly releases, even when you continue to hold down the ExpressKey or pen button.

What you can do about it while we fix it: Uninstall the 6.3.40-2 driver and then install the 6.3.39-1 driver.

Now my Flip Manually keyboard shortcuts work when triggered from the Wacom Express Keys .

So the solution for people using Mac OS 10.14 (Mojave) and below is to uninstall the 6.3.40-2 driver and use the 6.3.39-1 driver.
(I am assuming for those using Catalina or Big Sur the current Wacom driver 6.3.42-1 should work properly for executing keyboard shortcuts from the Wacom Express Keys.
Driver 6.3.42-1 is incompatible with Mojave , but the older 6.3.39-1 works.)

I thought about your issue all weekend and it was getting frustrating that we couldn't even get the same issue as you! GLad you found the cause!