• 512-991-7197
  • This email address is being protected from spambots. You need JavaScript enabled to view it.
  • Always Open

Welcome to Microsoft Skype for Business Tips & Tricks

Skype File Transfer with the Least Possible Actions

Star InactiveStar InactiveStar InactiveStar InactiveStar Inactive

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.

© 2015 - 2020 Austin Laptop [AustinLaptop.Com]. All Rights Reserved.