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On-Premise SMTP Server sending to Cloud-based mailboxes

Posted on 2016-09-10
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Last Modified: 2016-09-11
We have a Hybrid set up. I have two On-Premise SMTP servers that need to send email to cloud-based users. These users do not have any email contact records On-Prem as they are strictly cloud-based. As the SMTP servers try to send to these cloud-based users, the On-Premise queues are filling up b/c the SMTP servers are pointing to the On-Premise Exchange servers for delivery. We currently use 'tenantName.mail.protection.Outllook.com and tenantName-org.mail.protection.Outlook.com for email routing to users that have been migrated to the cloud. (They have On-Prem Remote mailboxes for routing)

What SMTP settings should the On-Prem SMTP servers use to reach the cloud-based users?
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Question by:Anthony K O365
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Accepted Solution

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Vasil Michev (MVP) earned 250 total points
ID: 41792816
Simply create a mailuser/contact objects for these cloud mailboxes and populate their targetaddress attribute with the user@tenant.mail.onmicrosoft.com alias?
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Assisted Solution

by:Todd Nelson
Todd Nelson earned 250 total points
ID: 41792962
If you are attempting to send an email from an on premises application while you still have an on premises Exchange server configured for hybrid and AD doesn't know about the in cloud users, mail will get queued.

To avoid this problem, follow Vasil's guidance.  

Additionally, if you have hybrid configured, I would recommend creating the AD accounts on premise with a remote mailbox instead of a cloud only user.  That way you still can manage the object from a single location.

https://oddytee.wordpress.com/2016/05/05/provision-new-office-365-user-and-mailbox-from-exchange-hybrid-via-powershell/
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Author Comment

by:Anthony K O365
ID: 41793270
I was hoping not to have to create remote mailboxes for these 95k users, but it looks that's the way to go in this case. Thanks!!
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Author Closing Comment

by:Anthony K O365
ID: 41793273
I was hoping not to have to create remote mailboxes for these 95k users, but it looks that's the way to go in this case. Thanks gentlemen!!
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