Tips & Tricks

Learn new new tips, tricks, and shortcuts for making your Skype experience even better



Skype File Transfer with the Least Possible Actions

Welcome to the second installment in a new series of Tips & Tricks. The ‘Least Possible Actions’ series sets out to teach you the easiest way to perform common actions with Skype. In the first installment of this series I talked about starting a Skype call. Today I’ll show you the easiest way to send a file through Skype on Windows.

As always in this series, we’ll start from the point of your device being turned on and Skype being turned off.


To use the method which I will describe shortly, you will need:

  • Skype for Windows desktop installed with a shortcut or pin-to-Start which allows you to start it in one step.
  • Automatic sign-in enabled.
  • The name of the file you want to send.

Tip: To enable automatic sign-in, tick this box the next time you start Skype

Auto sign in


  1. Start Skype.
  2. Search for the group or contact you want to send the file to.
  3. Select it from the search results.

Contact searched and selected

  1. Search for your file name using the Search charm in Windows 8 (Win+F) or the Start menu in Windows 7.

File search

  1. Right click or tap-and-hold the file in the search results.
  2. Select Open file location.

Context menu

  1. Drag and drop the file onto the Skype icon on your taskbar.

Drag and drop

Least possible actions: seven.


The method I describe here is the easiest way for you to send a file through Skype in most cases. There are, however, two cases where you can do things a little bit quicker. The first case is if you don’t know the name of the file you want to send but you do know its location, and the second case is if you have the file on your desktop.

If one of those two cases applies to you, the quickest way to send your file is to press Ctrl+Shift+F after step 3 and then use the file explorer to browse to your file.


If you’ve got a common Skype task that you’d like to see a Least Possible Actions post about or you think you can beat my method, let me know in the comments or on the Skype Community.

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