Cannot Get Drag & Drop to Work

I'm trying to drag a photo from Evernote into Quicken.

Intended Steps:

  1. Mouse over transaction in Quicken.
  2. Active keyboard+trackpad trigger.
  3. Store current mouse position.
  4. Cursor moves to pre-determined location (over Evernote preview). Note: Drag & drop from this location works manually without any issues.
  5. Single-left click and hold in order to begin drag.
  6. Mouse returns to stored position.
  7. Single-left click released in order to end drag (i.e. drop the dragged image).

Image of BTT:

I don't have Quicken or Evernote, but I just tried your general steps and it seems to work fine here (Dragging a window).

Maybe one of these apps makes some assumptions about how a drag should behave and ignores the synthetic ones created in such a way.

No luck. I decided to run a simple drag & drop scenario to test the sequential actions in BTT - move a file on the desktop. BTT isn't working for me, but I can move the file manually with my trackpad. I recorded a screen capture to demonstrate.

I then added a few 'delay' actions in order to access each step. I'm I correct in saying that it appears that the mouse is moving back to the saved position prior to the file showing as selected? I recorded a screen capture to demonstrate.

I'm not sure what I'm doing wrong.

BTT Settings

OS X Trackpad Settings

I turned off my trackpad, connected a generic mouse, populated the gestures in BTT (trackpad section --> mouse section), and re-boot in OS X Safe Mode. I then loaded BTT and tested the actions again = same result. The mouse moves, highlights the file, but fails to drag it to the saved mouse location. I don't know what else to do / check / change.


Mouse Basic Settings

Unfortunately I also don't know, it seems to work fine here ;-(
Which macOS version and BTT version are you using?

OS X 10.14.3
BTT 2.717 (1027)

Interesting Update

As you can see in this video (link below), I still cannot move a file on the desktop; however, I can get an application window to move. If you watch the video closely, you may notice something else too: if the window is selected (blue) when I trigger the gesture, the application window moves as expected without any further action. If, though, the window is not selected (i.e., not blue) when I trigger the gesture, the application window does not move completely by itself - I have to do a manual single-finger tap on my trackpad at the very end for the window to relocate.

Andreas, any additional thoughts or suggestions? Do you find it odd that I'm able to move application windows with BTT, but not a file on the desktop?

Really hoped BTT would provide the functionality to perform this task. Maybe in the future.