We currently have a hybrid exchange Office 365 environment. I migrated a user to Office365 a couple of days ago without any issues. He had two smtp email addresses that referred to different spellings of his name. However, one of the smtp mail addresses was removed prior to migration. He then migrated successfully to Exchange Online. An example of his email addresses were firstname.lastname@example.org and email@example.com
However, people from within the company who still used one of his old smtp email address of john.smyth complained they could no longer send email to him. The old smtp email was then re-entered into Attribute Editor in AD under MSExchShadowProxy address and ProxyAddresses. This has now replicated to Office365.
However, users are receiving and error message:
Delivery has failed to these recipients or groups:
There's a problem with the recipient's mailbox. Please try resending the message. If the problem continues, please contact your helpdesk.
Diagnostic information for administrators:
Generating server: EmailServer.domain.com
#550 5.2.0 RESOLVER.ADR.BadPrimary; recipient primary SMTP address is missing or invalid ##
Original message headers:
Received: from MailServer.domain.com ([::1]) by MailServer.domain.com ([::1])
with mapi id 14.03.0301.000; Thu, 20 Oct 2016 08:43:07 +0100
Content-Type: application/ms-tnef; name="winmail.dat"
From: Johnny Appleseed <firstname.lastname@example.org>
To: John Smith <email@example.com>
Date: Thu, 20 Oct 2016 08:43:07 +0100
I have tried removing the cache from users outlook files, NK2, and even selected the user manually from the global address list and it still returns with a failure. I have even tried to send email to his mail.onmicrosoft.com account which bounced back. However, some users are able to email him without any issues. The error message is trying to send it to the x500 address that is listed under his email addresses.
Any ideas on how to resolve this?