Deliverability to outlook.com is based on your reputation View data view ip status request access access control edit profile faq junk mail reporting program request access step 3 of 3 unknown authorization request id. The outlook.com smart network data services (snds) gives you the data you need to understand and improve your reputation at outlook.com.
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It is against outlook.com policy to send mail from a machine which is an open proxy server, and it will be blocked from accessing some or all of outlook.com servers as long as it remains in that state.
This site provides information to information technology professionals who administer systems that send email to and receive email from outlook.com
It also provides some information about how users with outlook.com accounts can report junk email and phishing attempts.