The customer uses Jira onPremise in connection with an Exchange Hybrid whereupon Jira authenticates itself against the onPrem Exchange Server.

Remote Server returned ‘550 5.4.1 Recipient address rejected: Access denied. AS(201806281) [ZR0CHE01FT015.eop-che01.prod.protection.outlook.com 2024-02-01T14:50:04.245Z 08DC23158B19B76B]’

NDR from an Testmail

PROBLEM

One customer received the message that certain users were not receiving mails from an onPremise application, while for the most of the users the mail flow worked without any problems.

The customer tried to send mails via the Jira Admin Portal, for the users where the mailflow worked the same message appeared as for the users where the mailflow did not work. Jira always reported that the mail was successfully forwarded to the Exchange.

With “get-messagetracking” Powershell we have seen that the onPremise Exchange is getting the Mail, but the last SMTP StatusID is and “FAILED”

SOLUTION

The Affected Users did not have the correct remote Routing Adress @tenant.mail.onmicrosoft.com.

So the Solution is, to add the correct Proxy Adress with tenant.mail.microsoft.com to the affected User Accounts to solve the Problem: