Outlook 2011 shipped with incorrect POP3 information for MSN accounts, so the “autconfigure” feature doesn’t work correctly. Most of the data on Microsoft’s supports site is incorrect or out of date, but the following URL is closest to correct:
There are some errors — follow these steps
1. Open the accounts preference pane from within outlook ( not the OSX Accounts pane, but the outlook specific accounts pane ) as per the MS support instructions.
2. Add/modify a POP3 connection as per the MS support instructions.
3. Set the Incoming POP3 server to POP3.live.com, select use SSL on port 995. Do not select the “Always use secured password” check mark.
4. Set the outgoing SMTP server to smtp.live.com, select use SSL, on port 587. You will need to select “Override Default Port” check mark to do so.
5. For the incoming username, type your email address, including the @foo.bar ( e.g. Someone@msn.com — not just the user-name. )
6. Set the SMTP server to, “Use Incoming Server Info” by clicking the “More Options” button.
Viola, Outlook 2011 for the Macintosh will now work correctly.