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In my Azure trial environment, I have successfully run HCW (Hybrid Config Wizard) and migrated a mailbox from On-Premise Exchange 2016 to Office 365.

I was able to use Outlook 365 to log onto the just migrated O365 mailbox and send emails out. However, I was not able to receive any emails in the O365 mailbox. I saw that the emails are all stuck in the queue viewer of my On-Premise Exchange Server.

Currently, the MX record is still pointing the On-Premise Exchange Server and so incoming emails to O365 mailbox will need to rely on the Send Connector called "Outbound to Office 365" in On-Premise Exchange Server.

Here is what I found in the "Outbound to Office 365" Send Connector. I saw that it was using the MX record option which I think is incorrect.

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So, I chose the Smart Hosts option in the screenprint below.

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However, it still did not fix the problem.

Any thoughts?

Blue Tongue
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  • Could you update the question with the error text from one of the stuck messages? What's the default route for email to external recipients (i.e gmail.com), does your server use MX records for this? (If not then confirm your server can send outbound on port 25) or a Smart Host? (If yes then use it for this route) – jfrmilner Jul 27 '20 at 18:35
  • Make sure your MX Record is still pointing at your on-premise exchange and then open up the user and ensure an appropriate proxy routing address is set for the user, otherwise Exchange won’t know where to send the mail – Timothy Frew Jul 27 '20 at 21:16
  • @TimonthyFrew: 1) MX record is still pointing to On-Premise Exchange 2) User's attribute proxy address already the routing address user@.mail.onmicrosoft.com 3) User's attribute TargetAddress is the same as, i.e. user@.mail.onmicrosoft.com – Blue Tongue Jul 28 '20 at 00:03
  • @jfrmilner There are 2x Send Connector for On-Premise Exchange. The first one is an "Outbound to MailJet" which I used (before Office 365) to send all outbound emails through Mailjet Smarthost and it has been working fine. Yes, there is an MX record that points to the On-Premise Exchange Server. The second one "Outbound to Office 365" send connector was added by HCW and it is not working. – Blue Tongue Jul 28 '20 at 00:12
  • @jfrmilner, in the queue viewer, the stuck message's error is 4.4.7 Message delayed – Blue Tongue Jul 28 '20 at 00:47
  • Check your Exchange server can send traffic outbound on Port 25 to Microsoft – jfrmilner Jul 28 '20 at 10:10

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