Outlook/Hotmail seems to be blocking some essential emails.

Question

Outlook/Hotmail seems to be blocking some essential emails.

Mark 5

I am having the same problem that was reported by another user in January.

I'm trying to login to a site that uses a two-step process. The second step is in that login process is that the site sends an email with a Iogin link.

I have been able to login to that site in the past, but in the last week this stopped working. The site says it has confirmed delivery of those emails, but none of them have arrived in my Outlook mailbox. They are not in my junk folder or any other folder. I tried multiple times yesterday and again today. This means I have lost the ability to use that site.

I read the previous reply and followed the steps to get help from a human. That worked, eventually. The person I chatted with gave me instructions on how to fix the problem. I was told to manually disable all of my rules and reset my junk mail settings to "standard." Because I have a lot of rules, those instructions took a long time and my human assistant was not able to stay online while I carried them out.

Unfortunately, after completing those steps, the problem is not solved. And now it appears that I can no longer reach a human for follow-up technical support.

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2 answers

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Answer 1

Brian Tillman 27,320 Independent Advisor

That's about the best anyone can do. Sorry it's so dissatisfactory.

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Answer 2

Brian Tillman 27,320 Independent Advisor

Hi. I'm Brian and I'll try to help.

This is a problem reported by many. You should recontact someone at Microsoft using the Help feature in Outlook.com and tell then the server is blocking the messages; that they aren't arriving in the mailbox at all because you have no rules and the messages aren't moving to the Junk Email folder. In case you don't know, here is an image of how to use the Help feature.

Outlook Help

Mark 5 Reputation points

2026-10-02T02:45:35.6866667+00:00

If this is a COMMON problem, it seems like Microsoft not developing a GENERAL fix, instead of forcing INDIVIDUAL users to jump through hoops?
Brian Tillman 27,320 Reputation points Independent Advisor

2026-10-02T14:57:44.96+00:00

I, like everyone else here, am just a user like you. I have no influence in setting Microsoft policies. All I can do is point you toward available methods that may help.
Mark 5 Reputation points

2026-10-03T02:05:49.88+00:00

I did find my way to the chat and eventually (after three tries) connected with a human. The estimated wait times were wildly inaccurate and I only connected on the third try. The person told me there was nothing he could do without an actual email from the sender. Quite the Catch-22! He said the only solution was for the sender of the blocked emails to work with Microsoft tech support. I'll report if that works.

I left several user satisfaction responses saying I was highly dissatisfied and that this was a problem Microsoft had created and Microsoft should fix.
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Mark 5 Reputation points

2026-10-03T17:23:00.4333333+00:00

I did find my way to the chat and eventually (after three tries and much waiting) connected with a human.The person told me there was nothing he could do without an actual email from the sender. He said the only solution was for the sender of the blocked emails to work with Microsoft tech support. I'll report if that works.