Not Impossible to Fix Outlook/Hotmail Delivery Problems

For reasons unknown, I recently started receiving rejections sent to outlook.com or Hotmail addresses from my MIAB. Hadn’t had any issues in a while. I am using a Linode virtual server and have been for several years. Early on I had problems and was also able to contact Microsoft to “mitigate the problem”. Of course, it wasn’t MIAB and it had become my problem when MS had problems with a range of IP addresses (IPV4) from Linode.

Well, after 3-4 days and at least 3 email exchanges, along with reports from mxtoolbox and one from a UK government server test, I received the email message below.

So those of you with the problem, be persistent. My takeaway is when they come to find out you are a real person, running a real email server according to all the standard conventions and protocols (DKIM, SPF, etc.) they will correct the problem.

++++++++++++

My name is ___________, and I work with the Outlook.com Deliverability Support Team.

We have implemented mitigation for your IP (****) and this process may take 24 - 48 hours to replicate completely throughout our system.

Sincerely,

Outlook.com Deliverability Support.

I had a similar experience 18 months ago. My Linode IP on the server I created for MIAB was on various blacklists. The most pernicious was the Microsoft blacklist which affected delivery for several of my users to their MS/Outlook using recipients. I diligently followed the instructions on each rejection message (that my users forwarded to me). I followed up by responding to each automated email I received. It was a tedious and frustrating process, and I had to use my Gmail account at times because my emails from my MIAB IP got rejected by the MS support site! :wink:

Eventually, after 10 days or so, a real human being at MS got involved, and, after several back-and-forths, the problem was mitigated within about a week. So, the better part of three weeks total to get the matter resolved.

I had also worked with my cloud hosting provider, Linode, and although they didn’t provide specific details, they indicated that they also took steps to ensure that the IP was excluded from lists (blocks) of IPs that are routinely blacklisted.

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The process for me was quite smooth as I used from templates from another thread on this forum providing MS with some information out of the gate they otherwise would request in a back and forth. Took me 3 days before MS confirmed that the implemented the mitigation for my IP.

However it does not solve my issues andmail still go to SPAM. I don’t have any problems sending to gmail and other local providers. Just MS so I am not sure what I could do next.

Generally if your email is going to spam then it is something wrong with your email. For this process deals with outright rejections by M$.

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I had exactly the same problem, but i followed this guide to solve it. It’s adapted to mail-in-a-box.

(If you need a translation, use this link)

There is no problem with the emails as such otherwise i would have had issues with other providers. Microsoft simply did not apply their “mitigation” actions correctly. I reopened the support case and they reapplied the “mitigation” actions. No issues since.

One more learning: if it does not get resolved after the first try, you need to persist.