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During my hybrid certificate renewal , have faced this Non Delivery Report belongs to Directory Based Edge Blocking issue , which i would share the Non Delivery Report with status code Status code: 550 5.4.1.
In middle of hybrid certificate verification / Renewal from the CA , DCV (domain Control Verification) specific email ID not receiving from external. The mailbox is located in Exchange 2016 on premise server and its hybrid environment.
Status code: 550 5.4.1
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More Info for Email Admins - Checks for Status code: 550 5.4.1
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This error occurred because a message was sent to an email address hosted by
Office 365, but the address doesn't exist in the receiving organisation's Office 365 directory. Directory Based Edge Blocking (DBEB) is enabled for
cloudmonkeys.xyz, and DBEB rejects messages addressed to recipients who don't
exist in the receiving organization's Office 365 directory. This error is
reported by the recipient domain's email server, but most often it can be
fixed by the person who sent the message. If the steps in the How to Fix
It section above don't fix the problem, and you're the email admin for
the recipient, try one or more of the following:
Check that the email address exists and is correct - Confirm that the
recipient address exists in your Office 365 directory, is correct, and is
accepting messages. - Yes its Correctly updated
Check for errant forwarding rules - Check for forwarding rules for the
original recipient that might be trying to forward the message to an invalid
address. Forwarding can be set up by an admin via mail flow rules or mailbox
forwarding address settings, or by the recipient via the Forwarding or Inbox
Rules features. - Working as expected
Make sure the recipient has a valid license - Make sure the recipient
has an Office 365 license assigned to them. The recipient's email admin can
use the Office 365 admin center to assign a license to them (Users > Active
Users > Select the recipient > Assigned License > Edit). - Yes - User is on-premise
Make sure that mail flow settings and MX records are correct - Misconfigured
mail flow or MX record settings can cause this error. Check your Office 365
mail flow settings to make sure your domain and any mail flow connectors are
set up correctly. Also, work with your domain registrar to make sure the MX
records for your domain are set up correctly. - Mail flow is working fine for other users who are located in the same on-premise server
Synchronize your directories - Make sure directory synchronization is working correctly, and that the recipient's email address exists in both Office 365 and in your on-premises directory. --- Checked and found the the Impacted users are belongs to the OU which is not synced to M365 AD [AAD} Resolution : Moved the user to the specific OU and done the delta sync Mail flow started working after the Sync completed.
For more information and additional tips to fix this issue, see this article.
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