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Exchange 2010 to Exchange 2016 on prem migration having major issues

Having major issues with an Exchange 2010 to Exchange 2016 migration.
We installed 2016 on a 2016 server and we are at the point where we are not getting any mail in or out. Nothing is working at all.
We have Spamtitan anti spam and our emails are collecting there but nothing is getting into exchange 2010 or 2016.

I have checked the firewall rules.
I have checked the send connectors and the receive connectors.
I have looked at the virtual directories.
I tried to open everything up by setting the ip ranges in most cases to 0.0.0.0 - 255.255.255.255

I'm seeing this in the Microsoft Connectivity Analyzer.
Attempting to send a test email message to asit@automationsolutionsinc.com using MX cloud8.spamtitan.com.
     Delivery of the test email message failed.

      Additional Details

The server returned status code 450 - Mailbox unavailable. The server response was: 4.2.0 <asit@automationsolutionsinc.com>: Recipient address rejected: Greylisted, see http://postgrey.schweikert.ch/help/automationsolutionsinc.com.html
Exception details:
Message: Mailbox unavailable. The server response was: 4.2.0 <asit@automationsolutionsinc.com>: Recipient address rejected: Greylisted, see http://postgrey.schweikert.ch/help/automationsolutionsinc.com.html
Type: System.Net.Mail.SmtpFailedRecipientException
Stack trace:
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at Microsoft.Exchange.Tools.ExRca.Tests.SmtpMessageTest.PerformTestReally()
Elapsed Time: 1191 ms.

Anything I try to send from 2016 OWA ends up in the drafts. I have created a user in the 2016 exchange server new. that fails as do all older accounts still in 2010.

Any suggestions?

Would uninstalling both 2010 and 2016 starting fresh and restoring the old mailboxes from backups be my best bet? We have like 35 so it is not the worst idea imaginable.

I have mot yet purchased and installed a commercial cert. That was next, but might that help?

Philip Elder

Are you using the Microsoft Exchange Deployment Assistant?

Matthew Cioffi

ASKER

Yes. Differed a little. I have not added a cert. I used a different name for external and internal. I can access all the external links and log in. I just cannot send or receive any mail yet.

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Philip Elder

Is the SEND Connector set up on 2016? Are the edge/firewall SMTP filters for outbound mail updated to include the new Exchange 2016?

Is the split DNS setup updated?

Hemil Aquino

We have Spamtitan anti-spam and our emails are collecting there but nothing is getting into exchange 2010 or 2016.

If spamTitan is collecting your emails then but you're not able to receive it then, you have routing issues.
Check the followings:

1- Inbound IP address from spam titan towards your exchange, make sure your public IP address is there.
2- If you are sending outgoing emails via SpamTitan make sure you have your smart host configured.
3- Make sure your default inbound connector is allowing Spam Titan address, or leave it as 0.0.0.0 255.255.255.255

Attempting to send a test email message to asit@automationsolutionsinc.com using MX cloud8.spamtitan.com.
Delivery of the test email message failed.

That means, Spam Titan caught your email but was unable to deliver it to your server due to communication issues.
Remediation, please log in to Spam Titan, select logs and then check the email message headers.

Message: Mailbox unavailable. The server response was: 4.2.0 <asit@automationsolutionsinc.com>: Recipient address rejected: Greylisted

Greylisted is because the domain is not listed as trusted into your Spam Titan account, after a few attempts trying sending email got graylisted, kinda like a blacklist, but it gets released after certain among of time.

Anything I try to send from 2016 OWA ends up in the drafts

Outbound connector issue, you need to verify your smart host.

Cheers,

Matthew Cioffi

ASKER

In the end MAS was super helpful in getting me up and running properly. We had some 1:1 messaging and he sorted me out very quickly.