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Travis HahnFlag for United States of America

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Windows Server 2003 SBS to Windows Server 2016 Essentials

Can this be done?  I am having issues with what appears to be the Schema.  The issue with the Server 2003 is that it appears to have a corrupt system file causing it to not be able to run windows update, and launching the update process over and over.

This is for a small client that has 4-5 users on the domain, and the server is just DNS/DCHP, and a file server.  Nothing else.  It used to be the mail server as well but we got them moved to Office 365.

I have tried to complete the Windows Essentials configuration but it fails each time.

I read that I may have to upgrade to 2008/2012 then to 2016 - but we don't have the license or the server to do that.  

There is no website tied to the current domain  (which is .local) or email.  Any thoughts?
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John
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Clarifying a couple of things:

1. This is SBS 2003 - there was no 64bit version of this.  Further, from 2003 onward (possibly 2000) you couldn't do an upgrade, it was ALWAYS a migration.  I didn't read the question to be trying to upgrade the OS but rather Migrate to the newer system.

2. It's not especially clear to me that 2016 won't work with 2003 - quoting the below link:
For customers who need additional time to evaluate moving their DFL & FFL from 2003, the 2003 DFL and FFL will continue to be supported with Windows 10 and Windows Server 2016 provided all domain controllers in the domain and forest are either on Windows Server 2008, 2008R2, 2012, 2012R2, or 2016.
https://docs.microsoft.com/en-us/windows-server/identity/ad-ds/windows-server-2016-functional-levels
It's not clear because 2016 can still run with DFL and FFL at 2003, but there should not be any 2003 DCs on the network - which would be the case here.  I don't know if there's a hard block against this or just advising you not to do it because something COULD happen (probably won't but COULD).

First concern I have is you said you didn't have a server to migrate temporarily to.  That's COMPLETELY UNTRUE.  Because you SHOULD be migrating to Essentials running in a VM.  Which means you can create another VM as a temporary system to migrate from 2003 to another version of Windows and then migrate to the essentials system.

Why should you virtualize?  Wrong question - why shouldn't you!  Please read: https://www.experts-exchange.com/articles/27799/Virtual-or-Physical.html

Alternatively (and again, you SHOULD be doing this virtual) you can just start from scratch - as you've stated, this is only 4-5 users.  The manual migration to a new domain is not all that time consuming for such a small network and would likely be FAR quicker than migrating to a 2008 or 2012 system before migrating to a 2016 system.
You've got a headache ahead of you with 2003. The hardware might another issue,  here's what Microsoft recommends https://blogs.technet.microsoft.com/infratalks/2012/09/06/transition-from-small-business-server-to-standard-windows-server/

I would do what the others are saying start from scratch with a new server and  5 users isn't that much and a lot less errors.
Not much to add here, but also consider that no matter how well maintained, the existing domain will have accumulated detritus (and probably some corruption / other similar issues) in the decade or more since it was setup, and that assumes it was setup correctly on day one.

I would not even consider migration - I would most definitely start from scratch, and re-create, then copy over the users' data and whatever else you need.

Also, whilst you may only have five users now, there is probably a good chance that you have legacy users sitting around on the system - you can leave all that behind too.

Hope that helps,

Alan.
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I wasn't looking to do an in place upgrade on same hardware.  We bought a HP Microserver (NO Visualized - because its one server) and we wanted to just transfer FSMO roles and data.  

It appears the easiest way is to just create a new domain and re-setup the 5 users in the domain.  Which is what I thought as well...

Thank you for all the help.
For just five users, setting up again is just as easy.