Hi all My environment is using Exchange 2010 and hybrid setup with O365, and majority of the users are in O365 already but I still have dozens of user stay in on-perm exchange 2010. We need to upgrade the exchange 2010 to 2016/2019 now due to the end of support, so if anyone can share with me the experience related to the below? I will add Exchange 2016 to the on-perm organisation, then I will change the public IP of those internet facing FQDN such as Autodiscovery, Outlook anywhere, EWS, OWA...etc to the exchange 2016 after we configured all URL/URL in Ex16 virtual directory. But I understanding the federation such as free/busy will also use the autodiscover and EWS to exchange the info. So if I change the public IP of those FQDNs to Exchange 2016, anything need to do to make the federation work? How about the mail connector between O365 and on-perm? Any best practice to migrate them from Exchange 2010 to Exchange 2016? If there nothing need to do in the above? Do we need to run the hybrid setup wizard again before we do decommission of the exchange 2010? Best regards Alex Tsang

Yes, run the Hybrid Wizard again after you make those changes. Ensure you apply a valid, trusted 3rd party certificate to the 2016 server that will be used for client / endpoint connections and set the URLs correctly. Change the source server on the on-prem Exchange Side from the 2010 server to the 2016 for any send connector Recreate any custom receive connectors you have in 2010 on the 2016 server. Ensure the 2016 has the same settings for the connectors that the 2010 server does for the hybrid mail flow Yes, re-run the Wizard and set to the 2016 server instead of the 2010. Detailed Steps: https://www.c-sharpcorner.com/article/hybrid-exchange-2010-to-hybrid-exchange-2016-part-one/ Use the latest version of the Wizard as well: https://learn.microsoft.com/en-us/exchange/hybrid-configuration-wizard-faqs

Installing Exchange 2016 into Exchange 2010 organization is like a normal migration procedure. You could refer to Microsoft official tool: Exchange Deployment Assistant https://assistants.microsoft.com/ Then run HCW (Hybrid Configuration wizard) to update the hybrid configuration. For your questions, my answers are as below: Run HCW again after you have changed all the configurations to Exchange 2016. It will update the hybrid configuration. When running HCW, it will allow you to choose where to create the connectors, just select Exchange 2016 server. Yes. For your reference: Step-by-Step: How to upgrade a Legacy Hybrid Exchange Server to 2016 https://www.itpromentor.com/upgrade-hybrid-2016/ Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information. If an Answer is helpful, please click " Accept Answer " and upvote it. Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

On-perm Exchange Upgrade when hybrid setup already done with O365

Alex Tsang 21

Hi all

My environment is using Exchange 2010 and hybrid setup with O365, and majority of the users are in O365 already but I still have dozens of user stay in on-perm exchange 2010. We need to upgrade the exchange 2010 to 2016/2019 now due to the end of support, so if anyone can share with me the experience related to the below?

I will add Exchange 2016 to the on-perm organisation, then I will change the public IP of those internet facing FQDN such as Autodiscovery, Outlook anywhere, EWS, OWA...etc to the exchange 2016 after we configured all URL/URL in Ex16 virtual directory. But I understanding the federation such as free/busy will also use the autodiscover and EWS to exchange the info. So if I change the public IP of those FQDNs to Exchange 2016, anything need to do to make the federation work?
How about the mail connector between O365 and on-perm? Any best practice to migrate them from Exchange 2010 to Exchange 2016?
If there nothing need to do in the above? Do we need to run the hybrid setup wizard again before we do decommission of the exchange 2010?

Best regards

Alex Tsang

2 answers

Andy David - MVP 142.9K Reputation points MVP

2021-02-14T13:13:05.607+00:00
Yes, run the Hybrid Wizard again after you make those changes. Ensure you apply a valid, trusted 3rd party certificate to the 2016 server that will be used for client / endpoint connections and set the URLs correctly.

Change the source server on the on-prem Exchange Side from the 2010 server to the 2016 for any send connector

Recreate any custom receive connectors you have in 2010 on the 2016 server. Ensure the 2016 has the same settings for the connectors that the 2010 server does for the hybrid mail flow

Yes, re-run the Wizard and set to the 2016 server instead of the 2010.

Detailed Steps:
https://www.c-sharpcorner.com/article/hybrid-exchange-2010-to-hybrid-exchange-2016-part-one/

Use the latest version of the Wizard as well:
https://learn.microsoft.com/en-us/exchange/hybrid-configuration-wizard-faqs
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Alex Tsang 21 Reputation points

2021-02-14T13:31:25.513+00:00

Thanks David

That means I need to run the hybrid wizard and choose the Ex16 server after I changed the internal/public IP to Ex16 server, then I can start to move the user mailbox from Ex10 to Ex16, am I correct?

So, if I run in 16 again, then I don’t need to run when we do decommissioning for Ex10, am I correct?

Best regards

Alex Tsang

Andy David - MVP 142.9K Reputation points MVP

2021-02-14T13:39:43.913+00:00

Thats what I would do, yes. Bring up the 2016 server, apply the correct certificate to it,
Run the Wizard, point it only at the 2016 - make sure things work, then move the mailboxes to 2016.

When you decommission 2010, you will not need to run the Wizard again, no. The Hybrid connection will only be using the 2016 server at that point

Let us know if you have any more questions. Thanks!

Alex Tsang 21 Reputation points

2021-02-15T02:05:04.177+00:00

Thanks David
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Jayce Yang-MSFT 1,251 Reputation points Microsoft Vendor

2021-02-15T03:04:48.807+00:00
Installing Exchange 2016 into Exchange 2010 organization is like a normal migration procedure. You could refer to Microsoft official tool:
Exchange Deployment Assistant
https://assistants.microsoft.com/

Then run HCW (Hybrid Configuration wizard) to update the hybrid configuration.

For your questions, my answers are as below:

Run HCW again after you have changed all the configurations to Exchange 2016. It will update the hybrid configuration.

When running HCW, it will allow you to choose where to create the connectors, just select Exchange 2016 server.

Yes.
For your reference:
Step-by-Step: How to upgrade a Legacy Hybrid Exchange Server to 2016
https://www.itpromentor.com/upgrade-hybrid-2016/
Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.

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Alex Tsang 21 Reputation points

2021-02-15T05:47:56.177+00:00

Hi Jayce

Thanks, and may I have the follow up questions?

I have read that step by step guide too, and this guide shows to change the Intranet/Internet user facing URL to the Exchange 2016 first, then migrate mailbox first and run the hybrid wizard in Ex16, at last do the Ex10 decommission. So after we changed the user facing URL to Exchange 2016, Exchange 2010 users’ OWA, ActiveSync and Outlook Anywhere connection will connnect to Ex16, and then EX16 will proxy the connections to Ex10 for the coexistence. In this excercise , the EWS will also go thru Exchange 2016 now, but we did not run the hybrid wizard at this moment. Then federation between on-perm mixed Ex10 and Ex16 exchange Org and O365 still work without any further configuration? Anything need to do with the certificate used for the federation?

Best regards

Alex Tsang

Jayce Yang-MSFT 1,251 Reputation points Microsoft Vendor

2021-02-16T02:03:23.48+00:00

Yes, you are right, there will be a short downtime before running HCW again. But it only takes a few minutes to re-run HCW.

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Andy David - MVP 142.9K Reputation points MVP

2021-02-16T02:08:53.973+00:00

There is no downtime if done right.

Andy David - MVP 142.9K Reputation points MVP

2021-02-16T02:11:27.74+00:00

You can simply run the Wizard at that point. The federation between 2010 will continue to work, then once you run the Wizard and point to the 2016 server, the federation will work between the 2016 server and 365. ( i.e. Free/Busy and such will go through the 2016 server)
There is no downtime, but it may take a few minutes for free busy to work again between 365 and the on-prem servers.

You should however run the Wizard and set it to the 2016 server Before moving any mailboxes to 2016. Otherwise, you will prob see Free/busy issues between on-prem and 365 mailboxes.

Jayce Yang-MSFT 1,251 Reputation points Microsoft Vendor

2021-02-16T08:49:00.75+00:00

Thanks for the supplement. The"downtime" is about EWS (Exchange Web Service), as Exchange 2010 cannot proxy EWS to Exchange 2016.

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Andy David - MVP 142.9K Reputation points MVP

2021-02-16T12:15:38.27+00:00

Correct, that's why its important to run the Hybrid Wizard and move all the client connections to the 2016 server first - before moving the mailboxes :)

https://techcommunity.microsoft.com/t5/exchange-team-blog/client-connectivity-in-an-exchange-2016-coexistence-environment/ba-p/603945

Jayce Yang-MSFT 1,251 Reputation points Microsoft Vendor

2021-02-18T08:39:32.95+00:00

Is there any update on this thread?Just checking in to see if above information was helpful.

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Alex Tsang 21 Reputation points

2021-02-18T18:29:35.45+00:00

Hi Andy

Appreciate your help, and I also think better run the hybrid wizard before we migrate the mailbox. But just for my curiosity, I also want to know if we change the public IP of Autodiscover and EWS to Ex16 first but without re-run the hybrid wizard, the federation will work or not, because the EX16 can proxy traffic to EX10.

Best regards

Alex Tsang

Alex Tsang 21 Reputation points

2021-02-18T18:29:56.103+00:00

Hi Jayce

Appreciate your help, and I also think better run the hybrid wizard before we migrate the mailbox. But just for my curiosity, I also want to know if we change the public IP of Autodiscover and EWS to Ex16 first but without re-run the hybrid wizard, the federation will work or not, because the EX16 can proxy traffic to EX10.

Best regards

Alex Tsang

Andy David - MVP 142.9K Reputation points MVP

2021-02-18T18:35:18.557+00:00

Ok, that breaks the "If done right" part :)
In that case, when you move the IP, the federation will stop working unless you also change the DNS to point to 2016 and have the same cert with the same subject and receive/send connectors set the same.

Optimally, you would use another public IP and have everything in place, and then you just run the Wizard ...

In this case, I would do this off hours, move the IP ,ensure you have the correct cert set
then run the hybrid wizard pointing at the 2016 server, ensure it works, then move the mailboxes.

Jayce Yang-MSFT 1,251 Reputation points Microsoft Vendor

2021-02-24T06:41:31.35+00:00

I agree with Andy's point of view, so I will not repeat the answer. If the issue has been resolved, please mark the helpful replies as answers, this will make answer searching in the forum easier and be beneficial to other community members as well. Thanks for your understanding.
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On-perm Exchange Upgrade when hybrid setup already done with O365

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