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We have a domain which is having issues sending emails to @hotmail and @live addresses. If you add the domain to safe senders it goes through no problem at all. However, sending to a random @hotmail/live address will never reach the recipient and will also not send back an NDR. It has all the relevant PTR and SPF records so that shouldn't be an issue.

Is there a blacklist checker for these Microsoft accounts we can use without the palava of having to go through either their forums or ridiculously large email support form?

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Unfortunately owing to hotmail/outlook/live addresses being free, Microsoft has very little (read: no) support for these addresses. After filling in about 5 online forms, we were assured that we would be contacted by someone on this matter... We weren't... Yesterday after throwing my toys well and truly out of the pram at them, they have raised a support ticket with MSN Support. – Martin Toy Mar 13 at 12:07

migrated from superuser.com Mar 7 at 16:11

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It's strange that you don't receive any NDR. You should also check logs of your mail-server.

The process of removing yourself from blacklist is pretty well explained in here: http://www.rackaid.com/resources/hotmail-blacklist-removal/ (this post is quite old, but not much actually changed since that time...)

Be ready that you'll need to spend some amount of time working on removing your domain from blacklist, AFAIK it can only be done manually by some Microsoft team.

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