[HN Gopher] Tell HN: Expect you may have to write off Microsoft ...
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       Tell HN: Expect you may have to write off Microsoft if you self
       host email
        
       I've had this IP for almost a decade. It's not on spamhaus, DKIM
       and SPF are correct, and I've signed up for MS's Junk Mail
       Reporting Program and Smart Network Delivery Services. They still
       reject my mail with  > Unfortunately, messages from [45.55.34.226]
       weren't sent. Please contact your Internet service provider since
       part of their network is on our block list (S3140). You can also
       refer your provider to
       http://mail.live.com/mail/troubleshooting.aspx#errors.  I went
       through their support channels and they were completely useless.  >
       Thanks for your patience while we investigated your request.  >
       Below your IP address(es) and their status(es) are listed.  > Not
       qualified for mitigation  > 45.55.34.226;  > The IP(s) above do not
       qualify for mitigation.  > Please note: This outcome indicates
       behavior that misses standards; please review Improving E-mail
       Deliverability into Windows Live white paper for helpful tips.  ...
       > What standards are missing? DKIM and SPF are passing and I got
       the IP taken off of Spamhaus recently. Other email servers like
       gmail aren't finding an issue.  ...  > Your IP (45.55.34.226) was
       blocked by Outlook.com because Hotmail customers have reported
       email from this IP as unwanted. One possible explanation for this
       is the automatic forwarding of unfiltered inbound messages,
       including unwanted messages, to Outlook.com/MSN addresses.  >
       Please confirm that your emails comply with Hotmail's technical
       standards.  > For more detailed information about best sending
       practices to Outlook.com users, please review Outlook.com Enhanced
       Deliverability white paper.  ...  > I've ensured there is no open
       relay, and I've only tried to send messages to my own Hotmail
       address so far. There are no other user accounts on this email
       server, just me.  > I've also signed up for the Junk Mail Reporting
       Program/Smart Network Data Services with that domain/IP. I don't
       see any incidents there.  > Around what day/time was email reported
       as wanted?  ...  > Thank you for contacting the Outlook.com
       Deliverability Support Team.  > As previously stated, your IP
       (45.55.34.226) do not qualify for mitigation at this time. I do
       apologize, but I am unable to provide any details about this
       situation since we do not have the liberty to discuss the nature of
       the block.  > At this point, I would suggest that you review and
       comply with Outlook.com's technical standards.  > We regret that we
       are unable to provide any additional information or assistance at
       this time.  I've gone through all the links they sent me and
       nothing is wrong with my email server. It's impossible that I could
       have ever sent spam. They just decided they don't like me for no
       reason and I don't get to send them mail.
        
       Author : jimmaswell
       Score  : 31 points
       Date   : 2023-04-24 18:56 UTC (4 hours ago)
        
       | codegeek wrote:
       | They are notorious for this and you are not the only. Not that
       | others are far better but MS absolutely is the worst at this.
       | Don't even get me started on their "Windows defender" flagging
       | websites as dangerous.
        
       | FeistySkink wrote:
       | Even with 'just' a custom domain tied to a 3rd party email
       | provider, with all the usual security stuff (DKIM, etc.)
       | configured, my emails and emails addressed to me sometimes are
       | marked as spam or disappear.
        
       | dpifke wrote:
       | It's not "your" IP address, it's DigitalOcean's IP address. And
       | DigitalOcean is unwilling or unable to police their IP address
       | space, so you've been lumped in with the other bad actors inside
       | 45.55.0.0/16.
       | 
       | There are lots of hosting providers that actually respond to
       | abuse reports, and thus have good email deliverability.
       | DigitalOcean isn't one of them. (I say this as someone who has
       | repeatedly reported spam and malware C&C to them, and AFAIK those
       | reports went to /dev/null.)
        
         | grepfru_it wrote:
         | >It's not "your" IP address, it's DigitalOcean's IP address.
         | And DigitalOcean is unwilling or unable to police their IP
         | address space, so you've been lumped in with the other bad
         | actors inside 45.55.0.0/16.
         | 
         | It's not an arbitrary search space, it's usually a /24 to
         | easily disqualify noisy neighbors and in addition the
         | reputation of ips registered in the ARIN record. I would urge
         | everyone to register any IP block they use that's more than a
         | /29. To the end of this story, I have successfully sent email
         | to microsoft servers from my /27 and /28 because (a) the /24
         | i'm on is not spammy and (b) my entire netblock is not spammy.
         | 
         | But even then I get certain random companies/universities that
         | will flat out reject my email because I'm not going through one
         | of the big 5 mail senders. I gave up, still host my own email
         | but relay my mail through an O365 exchange server
        
       | TheMagicHorsey wrote:
       | In theory the network should respect each IP address as if it is
       | held by a separate entity, who should be judged as an individual
       | and not as part of a group.
       | 
       | In practice, due to bad actors, almost all internet services will
       | in fact discriminate against you if your neighbors are (or have
       | been) assholes. Sometimes they even discriminate against your IP
       | address because they have PTSD about a different address that
       | looks like your address.
       | 
       | What can we do? Not a lot. If the customers of MSFT don't care
       | enough to complain that email is not being delivered to them,
       | MSFT doesn't care either.
        
       | KomoD wrote:
       | Yeah, Microsoft is always a pain in the ass when you're self-
       | hosting email, that's why I just don't bother.
        
       | lacoolj wrote:
       | I would say "switch to Vultr - it's what I use and I have no
       | problems at all" but considering what it takes to even spin up
       | e-mail servers, let alone get them to be functional, secure,
       | reliable, and _allowed_ , ... you are in a tight spot there
        
       | jonathantf2 wrote:
       | It's because the IP is on DigitalOcean - a hotbed for spam and
       | malware. I wouldn't bother self hosting e-mail any more because
       | you'll come across most providers just not accepting your
       | messages. Sucks, but is what it is.
        
       | gus_massa wrote:
       | In the university, we had some luck telling the students to send
       | us a message from their hotmail/live/outlook/whatever address.
       | This adds our address to some special secret list for that
       | account, and our messages (usually) reach them. (It may fail. It
       | may fail. IWOMM. YMMV. Sorry, but this is not a foolproof
       | solution, just a hack. Sending email to new people is still
       | difficult/impossible.)
        
       | tekeous wrote:
       | Microsoft is a pain in the ass regardless - they block my email
       | delivery from SimpleLogin. From their own servers.
        
       | quags wrote:
       | I know people are saying it's your isp and that is a possibility
       | but IMO ms is being too harsh here. First let me say at least
       | they have a support department unlike gmail. As for your isp I
       | honestly don't get a significant amount of spam from digital
       | ocean or many of these vps systems so I don't think it fair to
       | say that is the problem right away ( this is spam only not ssh
       | brute force scanning which I don't track ). I get significantly
       | more spam from aws, gmail and Microsoft itself - I'm personally
       | annoyed that these providers are too big to block but have no
       | issues blocking other ips with no ability to resolve it. Sorry I
       | have nothing to add to help resolve this. A month ago there was a
       | post on a similar issue but with gmail. At this rate the response
       | will be the problem is you are running your own email server and
       | should pay for delivery.
        
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       (page generated 2023-04-24 23:02 UTC)