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Tony Camas

Migrating Exchange Server 2010 (from SBS2011) to 2016 - Target OS?

Hi all,

I thought I posted this question yesterday, but it doesn't seem to be present among the posted questions in the community, so I'm trying again. Apologies if this is duplicated and I'm just not seeing it.

I have purchased the migration guide and tools for Migration of SBS 2011 and its included Exchange Server to Windows Server 2019 (actually 2022) and Exchange Server 2016, which I understand is the highest version that supports coexistence with (and thus migration from) Exchange Server 2010. But I'm confused about one point made (or seemingly made) by the guide. It keeps talking about migration to "Exchange Server 2016 on Windows Server 2016." I'm wondering if that means the target Operating System (where Exchange 2016 is installed) must be Windows Server 2016 or must be at least Windows Server 2016. I fear it's the former, which would be difficult since you can't buy Windows Server 2016 anymore (I don't think). As far as I know, there's no restriction preventing Exchange 2016 from being installed on Server 2019 or Server 2022, so what's the story here? Is there a real issue, or am I just reading too much into this?

Thanks for whatever info you can offer.


asked09/13/2024 17:41
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Last Activity 09/15/2024 14:45

1 Answer(s)

  • Mariette Knap
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    Tony Camas

    Hello Mariëtte, thanks for the swift response. Which yes, does help... but it's disappointing. :(

    I know that Exchange Server 2016 has the 180 day free trial, which yes, I was planning on taking advantage of in order to eventually migrate to a licensed Exchange Server 2019. But that 180 day free trial thing, that is offered for Windows Server 2016 (Standard) as well?  I was not aware of that -- is that what you're saying?

    -Tony

    Mariette Knap

    Tony,

    Windows Server 2016 can run as a trial for at least 180 days. If that is not enough you can extend that with 

    slmgr -rearm
    
    Or
    
    cscript.exe %windir%\system32\slmgr.vbs /rearm

    Why do you need 180 days for that migration? You should move to the newest versions asap.


    replied 09/13/2024 18:32
    Tony Camas

    Thanks for that tip.

    And of course I plan on migrating the rest of the way ASAP. I didn't say I was going to wait the full 180 days to move to the next version, just that I had that long if I needed it.  There actually might be some business (not technical) reasons (long story) why we might wait a couple of months to migrate the rest of the way, but six months? Not likely. Nice to know there is time to do it in a relatively leisurely way, though.

    Thanks again for the help (and the download link).


    replied 09/13/2024 18:58

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    replied 09/13/2024 18:22
    Mariette Knap

    A Windows Server 2016 ISO can be downloaded here Windows Server 2016 Trial

    Tony Camas

    OK, this project is going reasonably well; I have installed the member server running Windows Server 2016 Standard (trial edition) and am just about to start the install of Exchange Server 2016.

    But before I do, out of an abundance of caution, I would love to get confirmation of what I believe has been said here about the sequence of operations.

    I am basically migrating the SBS2011 system to a collection of three servers (three VMs in a fairly hefty physical machine). There is a DC, running Windows Server 2022 Standard edition in "core" mode (i.e., without UI). There is a general purposes (file/application) server running Windows Server 2022 Standard with UI that will take over as the file server for various shared folders we have, and also will be running some LOB applications in the background that are currently running on the SBS machine. And there is a mail server, which will run Exchange 2016 on Windows Server 2016 Standard (there is also a server that will run Exchange 2019 on Server 2022 as the final step, but we won't worry about that one for now).

    So I have installed and set up all the systems, I have created the new DC and added it to the domain, and I have begun migrating other things over. I have NOT yet moved FSMO roles and even though I'm pretty sure this will all be fine, I am reluctant to start the clock on SBS going out of license compliance until I absolutely have to.

    So, my question is, can I proceed with the Exchange Migration prior to moving FSMO stuff to the new DC? My understanding is that, as long as the new system is NOT running the Essentials role, I can do that.  Can you confirm that this is true? And if so, are there any caveats or anything that I should be paying attention to in this case that is not covered in the migration guides?

    Thanks again, in advance, for the assistance.

     


    replied 09/15/2024 01:52
    Mariette Knap

    So, my question is, can I proceed with the Exchange Migration prior to moving FSMO stuff to the new DC? My understanding is that, as long as the new system is NOT running the Essentials role, I can do that.  Can you confirm that this is true? And if so, are there any caveats or anything that I should be paying attention to in this case that is not covered in the migration guides?

    Yes, you can migrate Exchange Server 2010 to Exchange Server 2016 with the FSMO roles still on the SBS 2011. After you have completed this migration you should remove the old Exchange Server 2010 from the SBS 2011, see How to properly remove Exchange Server 2010 from SBS 2011. After removing the Exchange Server 2010 from the SBS 2011 the dashboard will no longer work and you need to use the standard tools in Windows Server like ADUC to add and remove users for example.

    BTW, you cannot migrate Exchange Server 2016 to Exchange Server 2019 if the SBS 2011 still runs Directory Services as the 'Domain and Forest Functional level' must be 2012R2 or higher.

    Migrations are complex procedures that require proper planning and you need to possess basic skills of ADDS, ADCS, DNS, IIS, DHCP, Exchange, Network layout, certificates and IP routing. Our guides are technically 100% correct but we do not have any control over what you do with it. If you follow the steps you should be just fine but the nature of migration projects require that you are prepared for the unexpected. Obviously, you can count on us when unexpected issues occur. 


    replied 09/15/2024 07:20
    Tony Camas

    Thank you again for being so helpful.

    I am aware of the necessity of removing the old Exchange Server when migration is done, and of course I plan on doing it. It's just that I have a fairly large number of users' mail to move, so I'm expecting the actual migration process to take a while (some of these folks have pretty big mailboxes), so I wanted to be able to get a head start on that and have those mailboxes moving in the background while I attend to other parts of the process. Much of that is done, but there's still some stuff left that I still need to finish.

    But I am indeed aware of the complexity; I've done a number of these myself over the years, but it's been a while since I did the last one (SBS 2011 being as old as it is), so I'm just being very cautious. And happily using your guides to double-check myself. While this is not "my first rodeo" by a long shot, you still have way more experience with this particular thing than I do (or that anyone does, most likely), so I'm grateful to have the backup, just to sanity check me, if nothing else. Also, this particular migration is a little trickier than usual because there is a large user base and they are working at 15 different locations, all connected by VPN. And complicating this further is the fact that the company's corporate offices (where the servers, old and new, currently are) are moving at the end of the month, and we are going to move all the head end stuff to a CoLo data center (which is probably where it should have been in the first place). But I want to finish the migration before that, because I worry that the old server may actually not survive the move. in reality, that's probably an exaggeration, but I worry about it anyway. So I have really only about a week and a half to wrap this up.

    Anyway, you don't need to hear this; I just wanted to give you an idea of why I'm being so tentative. I'm sure this will turn out fine. I just want to be sure to avoid having to do anything twice, as I really don't have the time for that. Knowing that I can move the mailboxes while doing other stuff helps enormously in that regard.

    Thanks again. Hoping I won't need to bother you anymore!


    replied 09/15/2024 07:43
    Mariette Knap

    No problem Tony. You better ask if you have questions.


    replied 09/15/2024 14:45

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    replied 09/13/2024 18:19
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