Does Outlook.com allow you to whitelist email addresses? I would be surprised if that feature was not available, although I suppose that it wouldn't be all that shocking if the makers of MS Bob(*) failed to provide whitelisting.
(*) If you entered the same wrong password into MS Bob 3 times, it would prompt you for a new password that was easier to remember -- and then accept it.
Micorsoft's Outlook.com email service marks emails form this list as spam currently. I recall something similar happening before but it was resolved. Can something be done with current issue?