We have a 2010 Exchange on premises configured with Hybrid right now. We have 3 mailboxes left on prem that should be moved to 365 in the next week or so. The objective is not to have any mailboxes hosted on prem, but install one 2016 or 2019 server for management, since that's still the requirement from MS. My questions are: Should we install 2016 while 2010 is still in production? If so, I'm having some issues with that where 2016 throws a "Deserialization error:..." and would not let me proceed with the installation. Should we decommission 2010 completely, then install 2016 or 2019 and use that for recipient management? Would really appreciate some clarification and guidance on that.

Put a valid, trusted cert on that server and assign the IIS services to it via the Exchange mgmt tools or set the autodiscover on it to $null https://video2.skills-academy.com/en-us/exchange/architecture/client-access/assign-certificates-to-services?view=exchserver-2019 or even better: Set-ClientAccessService –Identity 2016Server -AutoDiscoverServiceInternalUri $null then move the arbitration mailboxes to the new server after you have moved all the remaining mailboxes to 365 get-mailbox -arbitration | new-moverequest -targetDB <2016DB> Then remove the hybrid config IF you do not want to be in Hybrid! https://video2.skills-academy.com/en-us/exchange/decommission-on-premises-exchange#scenario-two FYI: For that error, you have a send connector that has that server as a source server. Go into EAC and remove it or use Powershell Using EAC under Mail Flow/ Send Connectors. Remove the server there from that send connector

I would install 2016 now before removing 2010. What is the exact error and have you prepped the AD Forest and are following the guidance to install 2016 into the forest and installing the latest 2016 CU? https://video2.skills-academy.com/en-us/exchange/plan-and-deploy/prepare-ad-and-domains?view=exchserver-2019 https://video2.skills-academy.com/en-us/windows-server/get-started/system-requirements

@YuriyK-1490 As Andy mentioned, we can install and upgrade to Exchange 2016 before uninstalling Exchange 2010. There are two Exchange server roles for Exchange 2016. They are Mailbox server role and Edge Transport server role. If you still need to manage users from on-premises, Mailbox server role is suggested to install. You can check this for more information about Exchange 2016 server roles: Server role architecture . If the response 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.

anonymous user David @Lydia Zhou - MSFT Thank you both for your assistance! When you get a moment, no rush, I'm curious which user attributes are being managed by the on-prem exchange in this configuration? Other people are talking about using ADSIEdit to manage them.

Decommision last Exchange 2010

YurokLA 51

We have a 2010 Exchange on premises configured with Hybrid right now. We have 3 mailboxes left on prem that should be moved to 365 in the next week or so. The objective is not to have any mailboxes hosted on prem, but install one 2016 or 2019 server for management, since that's still the requirement from MS. My questions are:

Should we install 2016 while 2010 is still in production? If so, I'm having some issues with that where 2016 throws a "Deserialization error:..." and would not let me proceed with the installation.
Should we decommission 2010 completely, then install 2016 or 2019 and use that for recipient management?

Would really appreciate some clarification and guidance on that.

Accepted answer

Andy David - MVP 144.4K Reputation points MVP

2020-10-20T22:30:11.073+00:00
Put a valid, trusted cert on that server and assign the IIS services to it via the Exchange mgmt tools or set the autodiscover on it to $null

https://video2.skills-academy.com/en-us/exchange/architecture/client-access/assign-certificates-to-services?view=exchserver-2019

or even better:

Set-ClientAccessService –Identity 2016Server -AutoDiscoverServiceInternalUri $null

then move the arbitration mailboxes to the new server after you have moved all the remaining mailboxes to 365

get-mailbox -arbitration | new-moverequest -targetDB <2016DB>

Then remove the hybrid config IF you do not want to be in Hybrid!

https://video2.skills-academy.com/en-us/exchange/decommission-on-premises-exchange#scenario-two

FYI:
For that error, you have a send connector that has that server as a source server.
Go into EAC and remove it or use Powershell

Using EAC under Mail Flow/ Send Connectors. Remove the server there from that send connector
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1 person found this answer helpful.
YurokLA 51 Reputation points

2020-10-21T18:13:55.287+00:00

Thank you, AndyDavid.

For autodiscover, I removed the 2016 SCP via ADSIEdit, which is effectively the same thing as doing it in Powershell (not as elegant, though :) ).

You put a big IF in your Hybrid statement; please clarify. If all of my mailboxes are in 365, and the source of authority (AD) is still on-prem, and we're using DirSync, why would I have a need for Hybrid? The plan, at least while the AD is still on-prem, is to create users and mailboxes via the New-RemoteMailbox command, and not have to rely on any Hybrid features. Am I missing something?

Andy David - MVP 144.4K Reputation points MVP

2020-10-21T19:30:09.6+00:00

Nope, no need for Hybrid in that case.

But, if you want to create or enable remote mailboxes you will need to keep that mailbox server you just brought up around to do that.
It sounds as if you are good to go once you move the remaining mailboxes and then you can remove the hybrid config.

Be sure to follow all those steps:

https://video2.skills-academy.com/en-us/exchange/decommission-on-premises-exchange#scenario-two

YurokLA 51 Reputation points

2020-10-21T21:48:28.013+00:00

Thank you, AndyDavid. Yes, I will follow the Scenario-Two steps for sure.

YurokLA 51 Reputation points

2020-10-21T21:55:16.44+00:00

A follow-up question to your "...if you want to create or enable remote mailboxes you will need to keep that mailbox server..." :

is there another way, besides using the New-RemoteMailbox cmdlet, to create an on-prem user with the cloud mailbox?

Andy David - MVP 144.4K Reputation points MVP

2020-10-21T22:01:37.763+00:00

well that and enable-remotemailbox which enables an existing AD Account as a remote mailbox.

Those are your options.

Andy David - MVP 144.4K Reputation points MVP

2020-10-21T22:27:25.877+00:00

By the way, if you are all set, please mark any answer as accepted so we can close this up. thanks!
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3 additional answers

Andy David - MVP 144.4K Reputation points MVP

2020-10-19T18:46:52.62+00:00

I would install 2016 now before removing 2010.

What is the exact error and have you prepped the AD Forest and are following the guidance to install 2016 into the forest and installing the latest 2016 CU?

https://video2.skills-academy.com/en-us/exchange/plan-and-deploy/prepare-ad-and-domains?view=exchserver-2019

https://video2.skills-academy.com/en-us/windows-server/get-started/system-requirements
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YurokLA 51 Reputation points

2020-10-19T18:55:02.357+00:00

Hi Andy,
Thanks for the quick reply. Well, according to this article - https://video2.skills-academy.com/en-us/exchange/plan-and-deploy/prepare-ad-and-domains?view=exchserver-2016#step-1-extend-the-active-directory-schema, I can have the wizard do the prep for me, but like I said, the wizard throws the error (see attached image).

Andy David - MVP 144.4K Reputation points MVP

2020-10-19T18:58:50.49+00:00

Thats referring to the Exchange Setup Wizard, not the hybrid wizard.

I would recommend you break out each step and prepare from the command line using an account with the correct permissions as noted in that doc

Setup.exe /IAcceptExchangeServerLicenseTerms /PrepareSchema Setup.exe /IAcceptExchangeServerLicenseTerms /PrepareAD Setup.exe /IAcceptExchangeServerLicenseTerms /PrepareAllDomains

YurokLA 51 Reputation points

2020-10-19T20:31:48.177+00:00

Got through that hurdle :). Thanks! Now, do I really need mailbox role or will only management tools suffice?

Andy David - MVP 144.4K Reputation points MVP

2020-10-19T20:37:37.62+00:00

If you want to use the 2016 server for a Hybrid endpoint, you need the mailbox role.
https://video2.skills-academy.com/en-us/exchange/server-roles#exchange-2016-hybrid-deployment

YurokLA 51 Reputation points

2020-10-19T21:54:57.497+00:00

If I'm only going to use 2016 for user management (no on-prem mailboxes, no SMTP services, no mail routing of any sort, all new mailboxes will be created in 365), please help me understand the need for the mailbox role on-premises.

Andy David - MVP 144.4K Reputation points MVP

2020-10-19T22:03:43.727+00:00

If you are going to remove the hybrid configuration
In this case, use scenario 2
Scenario 2 applies if using ADFS or AADConnect.

https://video2.skills-academy.com/en-us/exchange/decommission-on-premises-exchange#scenario-two
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Lydia Zhou - MSFT 2,371 Reputation points Microsoft Employee

2020-10-20T02:54:01.66+00:00

@YuriyK-1490

As Andy mentioned, we can install and upgrade to Exchange 2016 before uninstalling Exchange 2010.
There are two Exchange server roles for Exchange 2016. They are Mailbox server role and Edge Transport server role. If you still need to manage users from on-premises, Mailbox server role is suggested to install. You can check this for more information about Exchange 2016 server roles: Server role architecture.

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YurokLA 51 Reputation points

2020-10-20T22:19:02.41+00:00

LydiaZhou, I followed your advice and installed the mailbox role to my own demise. Now, some Outlook clients are seeing the certificate error pop-up, because 2016 registered as the SCP and clients are apparently trying to talk to it, but there is no cert on it. I'm now trying to uninstall exchange and re-install just the tools, and getting this error:

Lydia Zhou - MSFT 2,371 Reputation points Microsoft Employee

2020-10-21T08:45:58.76+00:00

If you want to keep the hybrid configuration and manage users from on-premises, Exchange mailbox server is required and you cannot just install the Exchange management tool to manage users.

If there are some user mailboxes on on-premises Exchange, you should configure the AutoDiscoverServiceInternalUri with appropriate FQDN and use valid certificate, then move them to Exchange 2016. If all user mailboxes are moved to O365, set AutoDiscoverServiceInternalUri to null for Exchange 2016.

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YurokLA 51 Reputation points

2020-10-21T18:20:10.56+00:00

Thank you for clarification, LydiaZhou.

I don't think I need to keep hybrid configuration. As I mentioned to AndyDavid...

If all of my mailboxes are in 365, and the source of authority (AD) is still on-prem, and we're using DirSync, why would I have a need for Hybrid? The plan, at least while the AD is still on-prem, is to create users and mailboxes via the New-RemoteMailbox command, and not have to rely on any Hybrid features.

Please help me fill any gaps I have in my understanding of the process and requirements.

Lydia Zhou - MSFT 2,371 Reputation points Microsoft Employee

2020-10-22T07:44:52.447+00:00

That's OK, you can remove the hybrid configuration and follow those steps in scenario two.

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YurokLA 51 Reputation points

2020-10-22T17:19:46.493+00:00

anonymous userDavid @Lydia Zhou - MSFT Thank you both for your assistance!

When you get a moment, no rush, I'm curious which user attributes are being managed by the on-prem exchange in this configuration? Other people are talking about using ADSIEdit to manage them.
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Andy David - MVP 144.4K Reputation points MVP

2020-10-22T17:33:00.737+00:00

All the Exchange attributes and features. Yes, you can use adsiedit, but not supported :)

YurokLA 51 Reputation points

2020-10-22T17:39:39.123+00:00

Right. Hence the reason for keeping exchange server on prem :)

Andy David - MVP 144.4K Reputation points MVP

2020-10-22T17:41:12.427+00:00

Exactly! :)
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Decommision last Exchange 2010

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