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Exchange Hybrid Migration to Office 365 - Single Mail User Not Receiving Mail from internal users

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 john.smith@domain.com and john.smyth@domain.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:
John Smith
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"
Content-Transfer-Encoding: binary
From: Johnny Appleseed <johnny.appleseed@domain.com>
To: John Smith <john.smith@domain.com>
Subject: FW:
Date: Thu, 20 Oct 2016 08:43:07 +0100
Message-ID: <4E1C978DDE70AE46B78B704228D983290106C4A71C@EmailServer@domain.com>
References: <>
In-Reply-To: <>
Accept-Language: en-US
Content-Language: en-US
X-MS-TNEF-Correlator: <4E1C978DDE70AE46B78B704228D983290106C4A71C@EmailServer@domain.com>
MIME-Version: 1.0
X-Originating-IP: []

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?
1 Solution
Marshal HubsEmail ConsultantCommented:
Please follow this link to resolve this error..
Zeeshan AfzalMicrosoft Technology ConsultantCommented:
you can confirm the primary smtp address by using below powershell command after connecting to office365

Get-Mailbox username| fl DisplayName, Primarysmtpaddress
kirk_shawAuthor Commented:
PS C:\Users\administrator.DOMAIN\Desktop> Get-Mailbox john.smyth@domain.com| fl DisplayName, Primarysmtpaddress

DisplayName        : John Smyth
PrimarySmtpAddress : john.smith@domain.com
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kirk_shawAuthor Commented:
Let me clarify something. His correct spelling is john.smyth, however people send email address to him as john.smith

His user login is john.smyth and his primary SMTP address is however john.smith as the majority of people have been sending to that address.

It would appear that Staff that have already been migrated to the Exchange Online have no issues with sending email to him, it's the staff that have not been migrated yet that are having the issues.
Todd NelsonSystems EngineerCommented:
You will need to create an X500 address for that user ... https://support.microsoft.com/en-us/kb/2807779

I had that issue after migrating PSTs to Exchange Online ... https://oddytee.wordpress.com/2014/08/22/imceaex-ndrs-after-migrating-psts-to-office-365/
Tej Pratap Shukla ~DexterServer AdministratorCommented:
Go through Exchange Server Deployment Assistant and selecting Hybrid options & then keep answering those questions which are being asked.
I hope it would help you.
Exchange Server Deployment Assistant: https://technet.microsoft.com/en-us/exdeploy2013/Checklist?state=3215-W-AAAAAAAAQAAAAAEAAAAAAAAAAAAAwAMAAAA~
kirk_shawAuthor Commented:
Resolved this issue myself. Turns out that I had, under ProxyAddresses in Attribute Editor to email addresses with smtp in capitals. Apparently the SMTP in capitals for an email address denotes the primary email address for that user and there was two like that in proxy addresses.
kirk_shawAuthor Commented:
I did the research myself and none of the answers provided pointed me in that direction to resolve the issue.

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