Outlook/Hotmail is no longer blocking my mail server

We go through this every few months. Here&#x27;s the recipe -<p>1. Visit <a href="https:&#x2F;&#x2F;olcsupport.office.com&#x2F;" rel="nofollow">https:&#x2F;&#x2F;olcsupport.office.com&#x2F;</a> and submit the complaint.<p>2. Wait for the auto-reply, followed by the &quot;Nothing was detected&quot; email.<p>3. Reply to the latter with &quot;Escalate&quot; in the body.<p>Within a day, they hammer shit in place and the block is removed.

I run a small transactional email provider (<a href="https:&#x2F;&#x2F;mailpace.com" rel="nofollow">https:&#x2F;&#x2F;mailpace.com</a>), our IPs are very rarely added to blocklists- but we are very strict on what we allow through our service, and surprisingly we’ve had no long term delivery issues with any of the big providers.<p>So thanks to the federated&#x2F;decentralized design of email, is totally possible to be part of the network without any special privileges.<p>We are sending millions of emails every day though, which is quite different to sending a couple hundred personal emails a week. If you’re running this on a cloud host, expect to be blocked by default. However if you can find a small vps provider you’ll have better luck on sending yourself.

Outlook&#x2F;Hotmail blocks DigitalOcean. After half a dozens attempts over the years to delist my IP, and following all the best practices (dedicated fixed IP, SPF, DKIM, DMARC, FCrDNS, zero spam, TLS, etc.) I gave up.<p>Eventually, most people realize that their Outlook&#x2F;Hotmail email service is defective because they&#x27;re not receiving emails, and they migrate to another email service.

I had this problem for years. I would get the block lifted and it would return in short order. I surmise it’s because my mail server runs on a VPS and other users on my subnet are not well behaved (actually I know this for a fact).<p>I solved the problem by paying for a next hop SMTPS server as an upstream smarthost for non-local mails. That means my mails come from a subnet that fronts TONS of other servers&#x2F;domains. That makes it a bigger headache for MS to block.<p>Sad but there you go. I do not use the external service for inbound. Inbound mails come direct to my server per the MX.

Wow, Outlook actually tells you they blocked you? My email (custom gmail domain btw) just ends up in the Spam folder of outlook clients with no notification at all.

I work on Microsoft&#x27;s anti-spam team, AMA!

&gt;When I try to reply his message in my mail client, it received the following error message:<p>&gt; <i>Delivery to xxx@outlook.com failed with error: outlook-com.olc.protection.outlook.com. said:...</i><p>He got error messages? I get mail silently dropped.<p>MS drops mail from my reputable mail servers - and from rep svs that send mail to MS accts I manage.

After many years of regularly getting blocked by Hotmail and outlook.com, I just decided to reject every incoming email from Hotmail and Outlook with an error message explaining the situation. If they don&#x27;t allow me to respond to emails sent by their customers, why would I allow them to send me emails in the first place?

I run my own mail servers and hotmail and other Microsoft-based email services regularly blocks my mail by source IP on the various domains I run.<p>I&#x27;ve been using the same &#x2F;29 network for over 15 years now. There&#x27;s no nearby adjacent networks that are on any blacklists.<p>I monitor blacklists on a regular basis.<p>No marketing. The domains I run are strictly personal and projects. I monitor volume and all kinds of stuff. I know there&#x27;s nothing like spam or any kind of marketing going outbound.<p>It&#x27;s astonishing how honest Microsoft is when I send them an email telling them to unblock. They literally just admit that they never had reason to block the domain&#x2F;IP and they unlist it for a few years and then it goes back on their list.<p>It&#x27;s become apparent that they blacklist by default.<p>Fortunately I only run into the occasional idiot who uses Hotmail or live.com.

GMail is the worst for email blocking resolutions. They don&#x27;t have an effective feedback loop built into their system. So when a user does block you, no one is told about it, to be fixed. Therefore lowering your reputation with them over time.<p>How can we as ESPs respond to them appropriately with removal of these people who don&#x27;t want our emails anymore, if we don&#x27;t know who the user is?<p>If there are any GMAIL service team members here, I would LOVE to know why a feedback loop was never implemented like the other providers.

Running a mail server should be something anyone can do. And while this is cool, there are so many other problems to do it. It&#x27;s the price we pay of letting big tech companies control so much of the virtual infrastructure: big tech has commoditized the internet so much into a platform for consumerism that it becomes a valuable target for spam.<p>In my opinion, the internet would be much better if none of the big players ever entered it, including Google, Facebook, Yahoo, etc, and it would allow for many more decentralized and valuable commons like email.

I ran into this issue several years ago. After complaining, MS allowed me to send email to MS properties (hotmail, live.com), but continued to block my email to their Office 365 clients.<p>I now use AWS SES to handle mail delivery. It&#x27;s free for up to 200 daily messages which is fine for me.

Maybe the big webmail providers are relying more on machine learning for filtering spam instead of blocking IP ranges these days.

Is this mira of a U.S. centric problem? I selfhost my mail in Germany, have one at a smaller mail provider and never had problems.<p>It is also not uncommon for companies to either have a local Exchange Server or use the mail service at their hosting provider. If everything is configured correctly, delivery works fine.

Side note - the privacy consent is downright aggressive. If you want to remove your consent you have to unselect 100+ checkboxes for each of the partners, whereas accepting is a simple &quot;accept all&quot;. I bypassed using reading mode, but darn...

&gt; Maybe the fake contact information of my Microsoft Account make them worry that I am not a good guy.

What if I don’t have a blog?

TL;DR emailed Microsoft a few times

I think that governments should offer one free email account per citizen for life. Which you could use or not, but is there for you as a digital inbox… which are the options?<p>- Self hosting is a bit elitist - not for the masses.<p>- A paid-for option (proton, tutta,…) would be cataloged as elitist. People perceive email as free.<p>- A free option provided by a Corporate player will gravitate towards monopolies and lack of privacy.<p>- A free for life government issued, easy to recover digital point of contact where all your government interactions are pointed towards would be a great step. You could still have a separate one if you don’t trust big brother, but at least your “recovery” address would be secure for life.

Why not avoid fighting these windmills by using any of the existing commercial mail relays for sending — like SES or mailchimp?