“Delivery has failed to these recipients or groups” when running Exchange in an Azure VM

Exchange didn’t used to be supported in Azure. It is now, subject to specific requirements; however there’s a big difference between “supported” and “works” and it was always theoretically possible.

My current customer has a test environment running on a number of Azure VMs. All was working well, until I started to test mail flow out of the organisation. My mailboxes (work and personal) are both on Office 365 and the reply came back as:

Delivery has failed to these recipients or groups:

Mark Wilson
Your message wasn’t delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept email from certain senders, or another restriction may be preventing delivery.

The following organization rejected your message: DB3FFO11FD037.mail.protection.outlook.com.

Basically, Exchange Online Protection was bouncing the mail. The error continued with diagnostic information for administrators and I could see that the message was leaving the organisation, then returning to the Exchange Edge server.

I could also see in one of the messages that it said:

“Remote Server returned ‘<DB3FFO11FD037.mail.protection.outlook.com #5.7.1 smtp;550 5.7.1 Service unavailable; Client host [123.123.123.123] blocked using FBLW15; To request removal from this list please forward this message to delist@messaging.microsoft.com>'”

So I emailed and asked to be removed, quickly receiving a very polite but understandably automated and non-committal response:

“Hello ,
Thank you for your delisting request SRX1234567890ID. Your ticket was received on (Aug 28 2015 12:26 AM UTC) and will be responded to within 24 hours.

Our team will investigate the address that you have requested to be removed from our blocklist. If for any reason we are not able to remove your address, one of our technical support representatives will respond to you with additional information.

Regards,
Technical Support”

Within 24 hours, Microsoft had responded to say that we had been delisted from their blocklists (presumably they checked that the IP address was one of theirs – which was also one reason why we couldn’t add a reverse DNS record, as one might expect with an SMTP server) and the mail had started to flow:

“Hello ,
Thank you for contacting Microsoft Online Services Technical Support. This email is in reference to ticket number 1234567890, which was opened in regards to your delisting request for 123.123.123.123.

The IP address you submitted has been reviewed and removed from our block lists. Please note that there may be a 1-2 hour delay before this change propagates through our entire system.

We apologize for any inconvenience this may have caused you. As long as our spam filtering systems do not mark a majority of email from the IP address as spam-like, your messages will be allowed to flow as normal through our network. However, should we detect an increase in spam-like activity, the IP address may be re-added to our block list.

Should you have any further questions or concerns, please feel free to respond to this email.

Thank you again for contacting Microsoft Online Services technical support and giving us the opportunity to serve you.”

I’m glad the experience was with a customer’s test environment, and not live email flow, but worth remembering for the future…

[Ticket numbers and IP addresses in this scenario have been changed]

One thought on ““Delivery has failed to these recipients or groups” when running Exchange in an Azure VM


  1. Microsoft is notorious for blacklisting IPs on their internal blacklist for hosted exchange/outlook.com/office365/Forefront even when the IP in question is not on any known public RBL and belongs to a properly configured mail server (correct PTR record, not an open relay, etc.). Glad you got action on it in less than 24 hours, I’m aware of several situations where any non-automated response or removal action took much longer. Hopefully the process is improved/streamlined in the future. It seems if you are an Office365 or premier customer (or if you have a customer who is and is willing to submit a ticket from their end), opening a ticket on O365 referencing the de-listing request number received in the initial automated response from Microsoft can expedite the removal action a bit.

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