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I find it little tedious to drop items in new email and make it an attachment. I need to resize both, source and destination window, so that I can pick and drop the item. This takes time. Yes few seconds more, but it matters.

Is it possible to drag an item from source window and then press command+~ (or command+tab) to chose a destination window and then drop it there? Any other easier solution available?

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The method you suggest should work fine -- start dragging, switch applications using keyboard, stop dragging. For, there's a built-in service called "New email with attachment", that you can access by right-clicking any file in the Finder. If Entourage supports Automator workflows, you could probably write a similar Service for Entourage using Automator. – scottishwildcat Mar 4 '11 at 16:33
up vote 0 down vote accepted

You can also begin your drag in the Finder (or your source), trigger Exposé, then drag the file onto the (shrunken) destination window. The window will flash a few times, and then Exposé will close with the destination window frontmost so you can drop your file.

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For most Macintosh applications that accept drag and drop, you can drag and drop files to their Dock icon. So your "flow" might be:

  1. Open the finder window with the file you want to send
  2. Drag it to your dock
  3. Drop it on the Entourage icon
  4. Entourage will launch and should give you a new message, with that file attached

Hope this helps.

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Although this answer is useful, it does not meet the need completely. This solution will not work when trying to attach while forwarding/replying to an email. Thanks. – LionHeart Mar 6 '11 at 5:29

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