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Send Files - Skype
How to send a file from your computer to one of your contacts in Skype. 
Step 1:
Select the contact from the contact list that you wish to send a file. Click the file icon in the bottom left corner.

Step 2:
Locate the file on your computer and select Open.

Step 3:Your file has been sent.

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https://helpdesk.etown.edu/helpconsole2012/KB/default.aspx?pageid=send_files