Hotmail Blacklist

Tim Makarios

New Email
I think I'm having the same problem as a lot of these people had, with Hotmail appearing to accept mail from my domain, but then not delivering it to the recipient. However, I'm an individual running my own mail server, not a company, so this hasn't been thoroughly tested on the scale of a mailing list.

So, first things first: Is someone willing to let me try sending an email to their Hotmail address, to confirm that my mail doesn't get there? (If you also give me a non-Microsoft-controlled address, I can CC the test email to that account, so you can see that I can successfully send email to people outside Microsoft's world, with valid SPF and DKIM and everything.)
 

EQ Admin

EQ Forum Admin
Staff member
Hi Tim,

Did you try creating your own outlook.com address for testing? Did any of the recipients reporting the missing email check their Junk folder and "Other email" tab?
 

Tim Makarios

New Email
Did you try creating your own outlook.com address for testing?
No; I was hoping to avoid entering into a 10,000-word contract with Microsoft simply in order to persuade them to deliver my domain's mail to their customers, or even just to test whether they're doing so or not. I thought it would be better to get help from someone who already has an address at a Microsoft-controlled domain.

Did any of the recipients reporting the missing email check their Junk folder and "Other email" tab?
One of my recipients said he checked all his folders; all three (unrelated) messages I've sent to him from my domain have gone missing, but he gets email I send from my old Gmail address. (And no, I haven't mis-typed his email address.)
 

Tim Makarios

New Email
I've checked with another recipient, who found my message to her Hotmail address in her Junk folder. On learning this, the first friend I checked with also checked his "Junk" folder (apparently not having previously realized that this was distinct from his "Unwanted mail" folder), and found my messages there, too.

So the next question is this: Why is Hotmail putting ordinary friendly emails from my domain into people's Junk folders? My IP address obviously hasn't been sending large volumes of unwanted mail, because senderscore.org still reports "Insufficient Mail Seen" from my IP address, and therefore won't give me a Sender Score. Also, mxtoolbox.com reports that I'm not on any blacklists.

I tried opening a ticket with Microsoft, but the result was that my IP address is "Not qualified for mitigation", whatever that means. I tried asking why it wasn't qualified for mitigation, but Microsoft seems determined not to give me any useful information, saying only that "I do not see anything offhand with the IP ... that would be preventing your mail from reaching our customers", and giving links to very generic information, much of which seems relevant only to businesses with mailing lists, not individuals like me running their own mail servers.

When I was first searching the internet for other reports of this problem, I came across { URL that doesn't state that - redacted by moderator}, which says "Hotmail won’t allow companies to email you unless they pay for the privilege (yes, they want people to pay money to send Hotmail members email)". At first I was sceptical, but one of the suggestions Microsoft gave me was to apply for the Sender Score Certified Mail programme, which I understand costs money. So it's starting to look a little more plausible now.
 
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EQ Admin

EQ Forum Admin
Staff member
My IP address obviously hasn't been sending large volumes of unwanted mail, because senderscore.org still reports "Insufficient Mail Seen" from my IP address

The lack of an email reputation isn't necessarily a bad thing, but it's also not a proven good sending reputation either. It's in the new/grey zone for some providers.

Do you have any other signals such as SPF and/or DKIM configured for your domain?

Are you sending from a shared or dedicated IP address? Sending from a shared relay is one reason why Hotmail might be rejecting your request.

much of which seems relevant only to businesses with mailing lists, not individuals like me running their own mail servers.

It's a standard form of questions that everyone opening a ticket needs to answer. Simply state that you're not sending email list related traffic from your mail server for those questions.

So it's starting to look a little more plausible now.

No, payment is not required to get email delivered at Hotmail / Microsoft.
 

Tim Makarios

New Email
Do you have any other signals such as SPF and/or DKIM configured for your domain?
Yes, as I mentioned in the first message, I've got both of those configured. I've even used online tools like dkimvalidator.com to verify that they're working correctly.

Are you sending from a shared or dedicated IP address?
Dedicated.

Simply state that you're not sending email list related traffic from your mail server for those questions.
I made this clear in my correspondence relating to the ticket, but the response was merely a reiteration of a subset of what they'd already told me.

No, payment is not required to get email delivered at Hotmail / Microsoft.
Maybe payment to Microsoft isn't required, but if I have to apply for the Sender Score Certified Mail programme in order to get my mail delivered to Hotmail inboxes, then payment to someone really is required.

By the way, I don't know why the URL in my previous message was redacted; did I paste the wrong one? I've still got a bookmark to the page that says the exact words that I quoted. See the attached screenshot; it's the second sentence in the first paragraph.
 

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