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Select “Accounts” from Tools menu of Outlook Mac 2011.

Choose the mail account you want to setup as SMTP Outgoing Server.
Outgoing Server Address: mail.live.com
Port Number: 587
Check these options: ‘Override default port’ and ‘Use SSL to connect’
In the Authentication drop down box, click to select Use Incoming Server Info.
Click OK.
Close the Accounts window.
Create a new email and try to send it to your self or another person