Windows Server 2012 Essentials to Windows Server 2016 Standard

[timeshifter]

What's the best way to go from a Windows Server 2012 Essentials to Windows Server 2016 Standard?

Customer has about 20 machines and runs an application that uses the Advantage database server. We're going to install a new server that came with Windows Server 2016 Standard. I've got the new server in my shop and have been experimenting.

I brought their backup in. Restored it to a new new Hyper-V VM and it worked nicely. Then I upgraded that Windows Server 2012 Essentials to Windows Server 2012 Standard. (I left the Essentials role in place after the upgrade). Then I did an upgrade install of Windows Server 2016 Standard. That all seemed to go well.

I was able to log in with one of their workstations to the "new" server and it seemed to work just fine. Changed the user's password to make sure it wasn't using cached credentials. I'm pretty happy with how it turned out but....

One thing I noticed was that I think it's still using 2012 Essentials role or code and it was labeled as such. Probably should have removed the Essentials role after going from Essentials -> Standard before going from 2012 -> 2016.

What's really bothering me is all the warnings not to upgrade from an older version to a newer one. You'll see these when you run the upgrade install from Windows Server 2012 to Windows Server 2016. They warn you that's it's not recommended especially for a domain controller (which this machine is).

I'm trying to avoid setting up a new domain then having to go around do a bunch of work on each PC: leaving and joining a new domain and related tasks.

How would you approach this?

 

[seedubya]

This covers most of it.

 

[YeOldeStonecat]

So just to rewind....
*Client originally had a DC, running 12r2 Essentials. Approx 20 users.
*LOB App runs on a database, brought in a second server....running Server 16 Standard.

Is there a reason to not just join that 2016 server to the domain and leave it as a member server? And ket the original 12r2 Essentials server keep going. Was the client going above 25 users so you need to upgrade licensing above what Essentials allows?

Upgrading from Essentials to Standard is quite simple.....there are some powershell commands to change the licensing...and then you go uninstall various features that Essentials has. You can opt to keep the Essentials roles and/or feature....I actually often install the Essentials dashboard on a lot of clients Server Standard installs, when the client uses Office 365...I like using the ease of management of the Essentials dashboard and sync the logins. Note...if your client uses the Remote Portal that the Essentials role puts in.....if you install it on Server Std...you need to get RDS CALs for users that will use it remotely.

 

[timeshifter]

So just to rewind....
*Client originally had a DC, running 12r2 Essentials. Approx 20 users.
*LOB App runs on a database, brought in a second server....running Server 16 Standard.

No. LOB app runs on that 12 Essentials along with DC, etc. It's the only server. New server brought in to replace everything.

Is there a reason to not just join that 2016 server to the domain and leave it as a member server? And ket the original 12r2 Essentials server keep going. Was the client going above 25 users so you need to upgrade licensing above what Essentials allows?

I don't think you can do that. My understanding is that Essentials does not allow any other servers on the network.

They haven't hit the 25 mark, but are on their way and figured it was best to go ahead and get the "bigger" one now.

Upgrading from Essentials to Standard is quite simple.....there are some powershell commands to change the licensing...

Yes, I did that. Went from:

• Windows Server 2012 Essentials --> Windows Server 2012 Standard (powershell command)
• Windows Server 2012 Standard --> Windows Server 2016 Standard (upgrade install)

It seems OK but I'm nervous about the warnings not to upgrade OS by the installer screens themselves.

 

[YeOldeStonecat]

I don't think you can do that. My understanding is that Essentials does not allow any other servers on the network..

Sure you can, I have plenty of Essentials networks out there with second member servers. SBS and Essentials happily allow member servers, you can even make additional DCs....you just need to leave the top fsmo roles with SBS and Essentials....keep it at the root of the domain/forest.

I've done lots of upgrades of server 2000 to 2003 and 2008 to 2012....no issues, have all been smooth. I have not upgraded 2012-2016...so..no experience there.

 

[timeshifter]

I've done lots of upgrades of server 2000 to 2003 and 2008 to 2012....no issues, have all been smooth. I have not upgraded 2012-2016...so..no experience there.

Well, hopefully I can add one data point for the 2012 --> 2016 upgrade path for you.

I just went through the process again last night:

• restore bare metal backup of their server to new VM
• Upgrade Windows Server 2012 Essentials --> Windows Server 2012 Standard (basically a command that changes the license)
• Remove Essentials Role from the newly created Windows Server 2012 Standard
• adprep /forestprep and adprep /domainprep
• Upgrade install from Windows Server 2012 Standard --> Windows Server 2016 Standard

So far so good. This is basically a repeat of what I did before but neglected to remove the Essentials Role in the process. Haven't decided if I'm going to add it back to 2016.

Will test a workstation on it hopefully tonight.