Keyboard shortcut has to be pressed twice

I have a shortcut in Better Touch Tool. Pressing SHIFT-down arrow while in DT, changes the label to green, adds the file to CURIOTA (only way is to OPEN WITH) and then returns the focus to DT. It works just fine when it runs.

However, I almost always have to press the key combo twice to get it work. I have tried different key-combos, adding delays in the execution of the steps, adding some next-item, previous item steps to make sure the file is selected before execution. What else could it be?

SHIFT + down is a default macOS shortcut. It adds the next item to the currently selected items

SHIFT + Arrow down

SHIFT is also a modifier in DEVONthink, when pressed it changes some menu items (but not sure whether that may have something to do with your problem).

I just tested this with SHIFT + down in BetterTouchTool and it works fine over here on Monterey.

Did you also try shortcuts without SHIFT?

Thanks for the suggestions. The SHIFT key issue was a good idea to check out but I tried several different combos and each requires the double entry. It’s almost like I have to “activate” the item first, and then click on it.

That’s indeed sometimes necessary and very confusing. However I think that’s only necessary in Apple’s own apps (e.g. it was only possible to trigger a service via shortcut after the menu was clicked once), not in BTT.

You could try to set a shortcut for the “green” menu (via System Preferences > Keyboard or via and then in BTT use an action that sends this shortcut to DEVONthink (instead of using BTT’s action that triggers the menu directly). Didn’t test but maybe it makes a difference.