To send a file from Windows Live Messenger (2011) to one of your contacts you have two options:
1st method
- In the dialog window with your contact click on the "Share" button and select "files on your computer"
- Select the file and click "Open"
- The file is uploaded to the dialog. Your contact must accept to start downloading the file on your computer
Note: do not close the dialog until it has finished downloading, the opposite is interrupted
The 2nd method
- In the MSN window, click the File menu and select "Send file"
- Select the contact in the window that opens and click OK
- Then select the file and wait your contact accepts the reception.