I’m sure many of you have seen this error when sending email to Hotmail/Outlook:
Unfortunately, messages from [IPHERE] weren’t sent. Please contact your Internet service provider since part of their network is on our block list
Typically this has meant that your IP space is not clean, and that Microsoft has blocked it from emailing their service. At least, that has been the prevailing thought, that they would be honest with this messaging. It seems that this is no longer true. I have been able to confirm that Microsoft will return this error when blocking content or sender, under unknown conditions. I’ll show my work:
From my relay:
Mar 27 14:45:10 relay-direct3 postfix/smtp[22758]: 3AFE73F04C: to=<{removed}>, relay=hotmail-com.olc.protection.outlook.com[104.47.13.33]:25, delay=0.21, delays=0.04/0/0.13/0.03, dsn=5.7.1, status=bounced (host hotmail-com.olc.protection.outlook.com[104.47.13.33] said: 550 5.7.1 Unfortunately, messages from [185.234.75.10] weren’t sent. Please contact your Internet service provider since part of their network is on our block list (S3150). You can also refer your provider to Troubleshooting. [HE1EUR04FT016.eop-eur04.prod.protection.outlook.com] (in reply to MAIL FROM command))
From the same relay one second later:
Mar 27 14:45:11 relay-direct3 postfix/smtp[22751]: C1B503F04C: to=<{removed}>, relay=grewada-nl.mail.protection.outlook.com[104.47.4.36]:25, delay=1.1, delays=0/0/0.48/0.66, dsn=2.6.0, status=sent (250 2.6.0 <{id removed}> [InternalId=2035814505849, Hostname=VI1PR10MB1901.EURPRD10.PROD.OUTLOOK.COM] 15682 bytes in 0.153, 99.524 KB/sec Queued mail for delivery)
From their support team just a few hours later:
We were unable to identify anything on our side that would prevent your mail from reaching Outlook.com customers.
So you see, it is now true that Microsoft returns errors that are misleading and false, and this is as close to their own admission as we’ll probably ever get.
Thank you for listening