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Trish BenningfieldFlag for United States of America

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Server 2016 ESSENTIALS, bringing into existing SBS 2008 domain

I have a customer with a SBS 2008 server (yes, the one with Exchange 2007) that is transitioning straight to Server 2016 Essentials version.  My questions are these:

1) I believe I found that I cannot migrate from this version of SBS, can anyone confirm?  The end goal is the remove the SBS server (Exchange is going online/cutover migration) and be left with just the 2016 Essentials with the roles and file shares.

2) Am I better off adding the existing pc's to a newly created domain on the Essentials 2016 server?  I have less than 10 client pc's and am fine with that if its the recommended method.

3) The server came preloaded and was already added to the existing domain manually and had the DC role added. If #2 is the way to go,  can I remove it without reinstalling to reset the wizard?

TIA!
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Cliff Galiher
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1) you can directly migrate.
2) This path is a significant interruption of end-user productivity. I recommend migrating if possible.
3) See #2.
I agree with Cliff that creating a new domain could be a productivity issue.  However, you do need to realize that you are jumping about a decade up in technology going from SBS2008 to WSS2016.  There are numerous new options and security fixes that have been implemented as well as different ways of doing things.  In addition, you have to look at migration in terms of your AD functional level, IPv6 readiness and security issues surrounding SMBv1/SMBv2, etc.

I mention all this because if you have the time and necessary skills, you could set up the new server separately from your present infrastructure.  You'd have to transition (re-create) group policies, mapped drives, shared folder structures, printer deployments, users and groups, remote access, etc. Then, you can transition all the workstations and users to the new domain with the WSS2016 server during a downtime window (over a weekend/overnight depending on your schedule).  This way, you have a chance to correct any previous bad configurations in your old network and you get to enjoy all the features available to you in your new, clean, WSS2016 environment.

Obviously, this could be A LOT of work depending on your environment and is only possible if you can afford the downtime and if you have a decent understanding of how to setup WSS2016.  If you need an overview, you can check out my blog at https://mytechiethoughts.com/series/server-2016-essentials-setup-guide 
I'm migrating the guide right now, but it's an overview of common WSS2016 setup tasks starting right from bare metal and including setting up DNS, DHCP, certificate services, IIS, remote access, integrated and offsite backup, etc.

Anyways, just thought I'd offer my two cents.  I think it's at least worth considering moving to a totally new infrastructure instead of migrating your decade old one.
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ASKER

Thank you both!  I did find the Migration Guide.  I have migrated and upgraded several SBS servers, and many more standard Windows Server versions, nothing with Essentials however.  My thought was also along the same lines as yours Asif-- the server is already so old and problematic with only a handful of users and systems, all with the same config and security.  Most of the client devices are Macs and aren't using any of the services short of DHCP and DNS.

The new Essentials 2016 server is added to the SBS domain  (was added through control panel, system, join domain) and reports it is a DC, but running the "Configure windows server essentials" consistently states the server needs to restart.  At this point I am looking for the fastest solution to get it properly functional.

TIA,

Trish
Your WSS2016 is joined to the same domain as the SBS2008?  SBS only allows for itself to be the DC, so that's a problem.  Are you looking at setting up a new domain?  If so, can you reinstall WSS2016 and start from scratch or do you have to keep using the existing install?  Let me know the answers to those questions and I'll be happy to give you an opinion on possible next steps.

I'd recommend a clean install with a new domain, especially so you can avoid any .local nonsense, but if you want to go another route, just let me know.
Yes, it was joined as a member server out of the box, and the ADDS role was added manually after; running the post-deployment configuration wizard launches the "Configure Windows Server Essentials" wizard, and it identifies the system is already a DC.  Configure fails with "Please restart the server and then run the configuration wizard again" error.  The system cannot be dropped from the domain either, as it knows its a DC.  No preference at this point, just looking for any light at the end of this tunnel to get out of this mis-step.  TIA very much. :-)
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Asif Bacchus
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HEAPING THANKS! I just took a look at your awesome docs and will using them to resolve this, have a wonderful day!
Thank you!
Glad I could help.  I'm literally migrating Part V (DHCP) in about an hour.  So It'll be up and ready for you to get cracking on your new server.  Best of luck, contact me on the site or via mail here if you need any more help!