Microsoft actively blocking DO IP range

March 27, 2018 2.6k views
Ubuntu Email
mark730939
By:
mark730939

Mail sent from my droplet is being returned when the recipient is MSN, Outlook or Hotmail

Mail.log excerpt;

Mar 25 19:40:58 box postfix/qmgr[4566]: 4AFDA2036C: from=clubmanager@————-.co.uk, size=1477, nrcpt=1 (queue active)
Mar 25 19:40:58 box postfix/submission/smtpd[28496]: disconnect from localhost[127.0.0.1]
Mar 25 19:40:58 box postfix/smtp[28928]: 4AFDA2036C: to=<—————@msn.com>, relay=msn-com.olc.protection.outlook.com[104.47.45.33]:25, delay=0.67, delays=0.09/0/0.43/0.14, dsn=5.7.1, status=bounced (host msn-com.olc.protection.outlook.com[104.47.45.33] said: 550 5.7.1 Unfortunately, messages from [159.65.85.119] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (AS3140). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. [CO1NAM04FT006.eop-NAM04.prod.protection.outlook.com] (in reply to MAIL FROM command))
Mar 25 19:40:58 box postfix/smtp[28928]: 4AFDA2036C: lost connection with msn-com.olc.protection.outlook.com[104.47.45.33] while sending RCPT TO
Mar 25 19:40:58 box postfix/bounce[28974]: 4AFDA2036C: sender non-delivery notification: F003928C01
Mar 25 19:40:58 box postfix/qmgr[4566]: 4AFDA2036C: removed

(I redacted the source domain and destination email ———-)

I have contacted DO support and they just say maintaining reputation is hard for them and to try changing regions or using a third party to relay email.

Anyone have practical experience of this issue and how to get around it.

I have a bunch of users that are seriously unhappy at the moment!

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4 Answers
Woet March 27, 2018

Do you use SPF/DMARC/DKIM? And why don’t you use a service like Sendgrid if deliverability is important?

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  • mark730939 March 27, 2018

    Yes, SPF and DKIM records are set.

    I would not say deliver-ability is especially important - this is just a mail server for a small voluntary organisation that deals with members of the public. They are all distributed users. I’m running mail-in-a-box so that they can use webmail.

    Many of their enquiries are from outlook and hotmail users.

    I do use postmark for transactional emails, but this is just general run of the mill email.

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    • Woet March 27, 2018

      It’s near impossible to maintain IP reputation. Some providers like Mailgun offer free packages.

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jasonjpeters March 27, 2018

Something else I have found with Microsoft is they also look to see if the PTR Records are present for the server. I have run into the issue with most cloud providers including Azure and AWS.

Here is another discussion that touches on this topic…
https://www.digitalocean.com/community/questions/how-do-i-setup-a-ptr-record

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I3litz April 5, 2018

As DO mentioned, try an external service, you can use Mailgun for it, it works nicely

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mark730939 April 5, 2018

As far as I know, Mailgun is of no use for general mail services, eg sending SMTP from a mail server (including attachments) - its just for transactional email?

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