I recently deployed a new Exchange server (2016). The end goal is to get rid of my 2010 server. The hybrid config wizard comes back with an autodiscover error, but the remote connectivity analyzer works without issue. The bigger problem, is I can't migrate a new exchange mailbox to o365, the migration says it can't find my mail server. o365 support says this is an on prem server issue so they can't help. It's funny, because this is only here to facilitate the use of o365. Anyway, there is an internal DNS A record for autodiscover pointing to the Exchange server. Also the (Get-MigrationEndpoint).Identity command returns nothing, but I don't get any errors regarding the creation of the migration endpoint. I am stuck and going in circles! Thanks!

an internal DNS record isnt going to help here. Have you met all the requirements including endpoints open on the firewall https://learn.microsoft.com/en-us/exchange/hybrid-deployment-prerequisites note: Configure the Autodiscover record for your existing SMTP domains in your public DNS to point to your on-premises Exchange servers (an Exchange 2010/2013 Client Access server or an Exchange 2016/2019 Mailbox Server).

Exchange (2016) Hybrid Migration

Accepted answer

Andy David - MVP 141.3K Reputation points MVP

2021-04-07T17:22:12.26+00:00

an internal DNS record isnt going to help here.
Have you met all the requirements including endpoints open on the firewall

https://learn.microsoft.com/en-us/exchange/hybrid-deployment-prerequisites

note:

Configure the Autodiscover record for your existing SMTP domains in your public DNS to point to your on-premises Exchange servers (an Exchange 2010/2013 Client Access server or an Exchange 2016/2019 Mailbox Server).
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Andrew Sarratore 21 Reputation points

2021-04-07T17:29:25.803+00:00

Since Exchange server 2010 was working fine, do I still need to check this? I don't control public DNS records for our domain, they are done through a 3rd party. Mxtoolbox shows the autodiscover.mydomain.com has an A record pointing to one of our public IPs. However I can't find a nat on the firewall for it.

Andy David - MVP 141.3K Reputation points MVP

2021-04-07T17:35:21.743+00:00

yes, if you want the 2016 server or the 2010 server to be the endpoint that is used to move mailboxes to 365, either server must meet those requirements

Andrew Sarratore 21 Reputation points

2021-04-07T17:38:42.997+00:00

Right, but the 2010 server was working just fine for migrations.

Andy David - MVP 141.3K Reputation points MVP

2021-04-07T17:52:21.22+00:00

and now you want to use the 2016 server for migrations correct? otherwise, why did you run the Wizard?
If so, then yes, you need to make sure everything is correctly set for the 2016 server.

Andrew Sarratore 21 Reputation points

2021-04-07T18:13:15.207+00:00

I found the NAT on the firewall. I changed the rule for a one to one with the new exchange server ip and still the same results.

Andrew Sarratore 21 Reputation points

2021-04-07T18:23:12.383+00:00

I found the NAT and updated it with the new Exchange server IP. But still running into the same issues. I have an IPV4 policy allowing all services as well.

Andy David - MVP 141.3K Reputation points MVP

2021-04-07T18:24:55.76+00:00

You have to a DNS record point to the 2016 server, not the 2010

Configure the Autodiscover record for your existing SMTP domains in your public DNS to point to your on-premises Exchange servers (an Exchange 2010/2013 Client Access server or an Exchange 2016/2019 Mailbox Server).

Andrew Sarratore 21 Reputation points

2021-04-07T18:29:43.303+00:00

Public DNS for autodiscover.mydomain.com points to a public IP that has a 1 to 1 nat on my firewall that points to the new exchange server. I can't point the public DNS to my on prem exchange server directly since we run a private ipv4 range behind a firewall. Mail.mydomain.com points to Microsoft ip ranges.

Andy David - MVP 141.3K Reputation points MVP

2021-04-07T18:32:48.863+00:00

If everything is set correctly, try running the Wizard again and see if you get any more errors.

Andrew Sarratore 21 Reputation points

2021-04-07T18:39:38.35+00:00

OMG I Got it!

The IPV4 policy was incorrect. How did this ever work before???

Andrew Sarratore 21 Reputation points

2021-04-07T18:46:17.953+00:00

It's good to go now. I am actively running a migration on a new email box to o365.
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Exchange (2016) Hybrid Migration

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