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What is the best way to drag a file from the desktop to an application when the screen is filled with windows that you don't want to manually move or adjust?

My current approach:

  • Run "Show Desktop" (using a trackpad gesture or hitting F11 on my older mac)
  • Select and hold the file with the trackpad
  • Hit F11 to exit "Show Desktop"
  • Drag the file on to the window

This works but it feels awkward because I need my left hand to cross over my body / keyboard to hit the F11 key while my right hand holds the trackpad down on the file.

Is there a better way to do this?

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    what if you drag the file to the dock icon of the app? Sep 9 at 23:56
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Set a hot corner to the Show Desktop Action. Slam the mouse into the corner, the desktop exposes, grab the icon from the desktop, slam the mouse into the corner again, the windows come back. Drop the icon into the window of choice.

Mission Control Window

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