Migrating from Server 2003 to Server 2019 using Storage Migration Service

Occasional Contributor

I'm trying to migrate from an unloved Server 2003 Std. SP2 installation that has been quietly chugging away in a closet for the last 15+ years to Server 2019 Standard, using the new Storage Migration Service.  However, Windows Admin Center, running on Windows 10 v1809, doesn't want to connect to Server 2003.  It keeps complaining that PowerShell 5.0 is required to make the connection.  As far as I know, Server 2003 only supports PowerShell 1 and 2.


Is there a step-by-step guide somewhere on how to do this particular migration scenario successfully?  I saw Ned Pyle's Ignite presentation on SMS and it looked incredibly smooth and simple.  Alas, it was using a much later version of Windows Server as it's Source Server.  The 2003 server has all of the Windows Updates, but perhaps there is something else that it needs to allow Admin Center to connect to it?  All ideas welcome!  :)


8 Replies

Might work through this one.



 "Supported source operating systems VM or hardware (to migrate from) :
Windows Server 2003" 


@Dave Patrick 

Thanks Dave, I had read that through, but the "All computers must be domain joined" had me thinking the wrong thing. Since it's a server, I was thinking that Server 2019 needed to join as another domain controller. Obviously that can't happen with a Server 2003 domain.. I've successfully joined the Server 2019 system as just another computer in the Server 2003 domain instead.


That brought me to the Admin Center error: "To perform a single sign-in using your Windows account, you might need to set up Kerberos constrained delegation". For future readers, I found this: https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2003/cc786828(v%3dw...) "Configuring Constrained Delegation for Kerberos" for Server 2003. However, it appears that this requires IIS be installed and running on the Server 2003 system. This server doesn't have the application server role (which appears to be required for IIS) installed. This may be a problem. ;) Do I have to install that role and configure IIS to proceed? It seems that the SMS process is a bit more complex outside of a large environment where many roles are more likely to have already been installed and running. This Server is just a standalone AD controller, also acting as a file server, DHCP, DNS, and WINS servers.


Thanks again!


I'm certainly glad that I planned to test this a few weeks before the scheduled cutover date.
:)  Ned made it look so easy! ;)


Maybe this one helps.


Not sure the end goal but may want to migrate the domain controllers as first step. Also better a option is to have file server role on a member server. If a single physical host then you might consider installing hyper-v role on host and stand up separate VMs for the different roles / applications.



@Dave Patrick 

Thanks Dave, it's a single 2003 Server, trying to upgrade to Server 2019.  Ned Pyle said it's easy during his presentation at Ignite 2018.  His demo migration was quick and painless.  Perhaps it is, if you have a datacenter equipped with old servers that already have every possible role configured on them.  However, my client base is small businesses (typically 5-10 users) that nearly always have just a single, ancient domain controller with a very basic configuration.  Administration is done at the console or via a remote console window.  No Admin Center or RSAT, etc.  I'm trying to drag them kicking and screaming into this decade and thought that SMS would make that process almost painless.


In trying to configure Single Sign-On from your link above, I'm getting the error: "The term 'Get-ADComputer' is not recognized..."  when I try to run the sample script .  Then further down in that document I see it says: "(Be aware that this requires a domain controller running Windows Server 2012 or later)."  Well, Server 2019 can't be a domain controller in the Server 2003 domain.  :(  I feel like I'm going in circles that lead back to Server 2003 not being able to do this.  Surely I'm missing something.  Hopefully something simple.  :)



That's correct, you cannot introduce a 2019 domain controller in a 2003 domain. DFL needs to be at least 2008 R2 and older FRS technology needs to have been migrated to DFSR. Which is why I mentioned the possibility of using hyper-v, give yourself more instances of windows to work with. To the issue I think the document was meant more for member server to member server migration, the domain controller adds a level of unexpected security and complications to the process. Might want to do it old school, add the File and Storage role, then do the migration of files using robocopy, otherwise I'd suggest starting a support case here with product support.







@Dave PatrickThanks Dave, the more I dig into this, the less it seems that the claim of SMS working with Server 2003 can possibly be true.  I found this document https://docs.microsoft.com/en-us/windows-server/manage/windows-admin-center/understand/faq that clearly states: 

"What versions of Windows Server can I manage with Windows Admin Center?

Windows Admin Center is optimized for Windows Server 2019 to enable key themes in the Windows Server 2019 release: hybrid cloud scenarios and hyper-converged infrastructure management in particular. Although Windows Admin Center will work best with Windows Server 2019, it supports managing a variety of versions that customers already use: Windows Server 2012 and newer are fully supported. There is also limited functionality for managing Windows Server 2008 R2."


Yet the current documentation for SMS relies on Windows Admin Center.  


Further down I find this: "Windows Admin Center relies on PowerShell capabilities and platform technologies that don’t exist in Windows Server 2008 R2 and earlier, making full support infeasible. Windows Server 2008/2008 R2 are approaching end of support in January 2020 so Microsoft recommends customers move to Azure or upgrade to the latest version of Windows Server.:


It would seem that the admin center document and the SMS documentation are at odds with each other.  The documentation for SMS should be updated with either a) a removal of the statement of it being capable of migrating from Server 2003 or b) define the exact requirements needed for a successful migration from Server 2003.  The current document defines an impossible set of actions for this scenario.  Quite disappointing.  :(  Thanks for the pointer to support, but I'm not part of some huge organization that can write Microsoft a huge check every year for support.  It's just me and a ton of conflicting documentation.  :(


You can provide this feedback to docs.microsoft.com authors at the bottom of the page.




For what it's worth, I too was having problems figuring out how to seamlessly migrate my 2003 file server to a newer OS (2019 server).

What I found is that the Windows Admin Center "CANNOT" manage the 2003 server but it "CAN" still perform the migration of shared folders and files from the 2003 server to 2019.  

You mentioned something about being joined to the domain and that it was a 2003 domain.  I believe you can join any OS to any domain but you cannot make newer Operating Systems (2019 server) a Domain Controller, unless you update the domain schema, etc. which may cause issues for your 2003 domain controller.

However, if all you are trying to do is migrate the file shares from 2003 server to Windows 2019 server, you should be able to do this.  In the environment that I just did it on successfully, all servers were joined to the domain.