Upgrading thru all version of Windows......server and domain controller

[opo]

Ive seen a couple of videos of people that upgrade client versions of Windows (even DOS) to Windows 8.1 or 10.

Im gonna try to do the same with the Windows servers........and take it a step up with domain controllers and active directory.

This is just for fun and learning purposes. Nothing at the end of the day and of course, this should never be used in a real life scenario.

My scenario is:

- VMWare Workstation

- Ill make a virtual network only for this

- 1 domain controller, 1 domain client

- Start from the oldest possible server/domain controller (Windows NT 3.1 Advanced Server) and upgrade to the latest possible server/domain controller ("Windows Server 10 Technical Preview")

- Start from oldest possible client that can join a domain (Windows NT 3.1) and upgrade* to the latest possible client that can join a domain (Windows 10).

* Upgrades will ONLY be done when the client cannot logon to the domain. What I mean by this is that Ill first install Windows NT 3.1 and Windows NT 3.1 Advanced Server. Ill upgrade Advance Server to the next version and check if I can logon. If I cant, Ill upgrade the client and recheck again. Meaning I want to upgrade the client as less as possible. If Windows NT 3.1 can logon to Windows Server 10 Technical Preview, awesome.

- On the server side, minimum features/changes will be installed/configured to check if they go thru the upgrade: Server name, admin user name/pass, client user name/pass, etc...

- Later versions of server/DC/AC, require some things that weren't available/needed. Windows NT 3.1 obviously doesn't need PDC Emulator but later versions of Active Directory, do. Those will be added/enabled STRICTLY as required. Also compatibility layers for previous clients will always be enabled to ensure that our oldest clients can logon/join.

- Server list:

Windows NT 3.1 Advance Server (All continuous operating systems will be the server version, first server and domain controller that will be installed)

Windows NT 3.5

Windows NT 3.51

Windows NT 4.0

Windows 2000 (first time Active Directory will be implemented)

Windows 2003 (or R2, I dont think there is MUCH differences in domain services between non R2 and R2 right?)

Windows 2008 R2

Windows 2012 R2

"Windows Server 10 Technical Preview"

- Client list:

Windows NT 3.1 (My goal is to stay on this version till Windows Server 10 Technical Preview)

Windows NT 3.5

Windows NT 3.51

Windows NT 4.0

Windows ME/Windows 2000 (Sadly, Im not sure if it is possible to upgrade from NT 3.51 to Windows ME so we would have to upgrade first to Windows 2000. If I have to go to Windows 2000, I am hoping that Windows 2000 is compatible with all future servers)

Windows XP (I really hope avoid having to reach this)

Windows Vista (I should NEVER reach this point)

If for some ODD reason, I have to upgrade past Vista, Ill take a step further as "bonus trial" and switch to a Linux distribution with Samba support. Again, I should NEVER even pass 2000 or at most XP)

- The procedure would go:

1: Install first server

2: Configure first server/DC/AD/etc,

3: Make a color scheme change on server to see if it passes thru upgrades

4: Make one domain admin account and make one domain user account

5: Install first client

6: Join client to domain using domain admin account

7: Logon using domain user

8: Leave/modify a file on the domain user's desktop to see if it passes thru

9: Upgrade to next server

10: Configure any changes that are absolutely needed

11: Apply fixes needed on server so oldest client can log on

12: Logon with domain user

13: If impossible to logon, upgrade client

14: Repeat from 9

For now, that is the idea. Am I on the right track?

I do need some points though as I've never done anything like this and AD is new to me as well.

What things am I missing that I should take in consideration?

Is my upgrade path correct? Maybe I'm missing that some arch are not compatible or not available

What are the minimum domain services I should have? As far as I know, barebones I have to have the PDC emulator, RID master, infrastructure master, schema master, and domain naming master. Once I hit Windows 2000, I think I should also enable a DHCP and DNS servers.

Not only will this take a while, but I also have to see how I can get and install all these operating systems!

[sc302 Veteran]

there is no direct upgrade for windows server until windows server 2008 to 2012.

 

there is no direct upgrade for dos to the windows nt platform (windows 2000, windows xp, windows 7, windows 8, windows 10). 

 

I wish you the best of luck, but being that there are no direct upgrades you are pretty much on your own.

[Studio384]

"should never be used in a real life scenario."

 

I don't know about you, but this is a real life scenario. 100% chance that there is a company out there somewhere that upgraded their server from 3.1 all the way up to 2012 R2, just not in 1 day, but a couple of years. This is a real life scenario, just in turbo speed.

[binaryzero]

What a waste of time.

[opo]

  On 29/03/2015 at 20:18, sc302 said:

there is no direct upgrade for windows server until windows server 2008 to 2012.

 

there is no direct upgrade for dos to the windows nt platform (windows 2000, windows xp, windows 7, windows 8, windows 10). 

 

I wish you the best of luck, but being that there are no direct upgrades you are pretty much on your own.

I thought the same thing but I saw this article: http://support.microsoft.com/en-us/kb/298107 and I thought it applied.

Does that article only apply to terminal services?

  On 29/03/2015 at 20:37, Studio384 said:

"should never be used in a real life scenario."

 

I don't know about you, but this is a real life scenario. 100% chance that there is a company out there somewhere that upgraded their server from 3.1 all the way up to 2012 R2, just not in 1 day, but a couple of years. This is a real life scenario, just in turbo speed.

In a real life scenario, I think most companies in the situation you stated, would go from NT to a clean Windows Server install...

[Max Norris]

  On 29/03/2015 at 20:37, Studio384 said:

I don't know about you, but this is a real life scenario. 100% chance that there is a company out there somewhere that upgraded their server from 3.1 all the way up to 2012 R2, just not in 1 day, but a couple of years. This is a real life scenario, just in turbo speed.

In a real life scenario, I don't see 2012R2 running on a machine that's approximately 20 years old from the Windows for Workgroups 3.1 era, where the minimum requirements were what, a 386SX with 4MB memory?  Think NT 3.1 was an SX with 12MB? That's not a "couple of years" worth of upgrades, that's a couple of decades.

[sc302 Veteran]

  On 29/03/2015 at 21:54, opo said:

I thought the same thing but I saw this article: http://support.microsoft.com/en-us/kb/298107 and I thought it applied. Does that article only apply to terminal services?In a real life scenario, I think most companies in the situation you stated, would go from NT to a clean Windows Server install...

The article states you have to perform a full install if the os doesn't support upgrade. I don't remember any server os having the ability to upgrade..god knows I have tried.

[binaryzero]

What's the purpose of this exercise? lol

[opo]

Due to difficulties, It seems I am going to have to start with a higher version of NT server.

[binaryzero]

I'd just start at Windows 2000 - I did an NT4 to AD migration every few months at my old job years back, you just migrate objects (build a new forest\setup a trust\move objects to new forest).

 

It isn't very exciting lol, I don't miss LAN\User Manager, or batch login scripts.

[opo]

On top of not having enough time, in the latest version of Workstation, they have removed the video recording ability. Gotta ccheck the best way to do it now and let me see if I can get some time in.

[sinetheo]

  On 29/03/2015 at 22:02, Max Norris said:

In a real life scenario, I don't see 2012R2 running on a machine that's approximately 20 years old from the Windows for Workgroups 3.1 era, where the minimum requirements were what, a 386SX with 4MB memory?  Think NT 3.1 was an SX with 12MB? That's not a "couple of years" worth of upgrades, that's a couple of decades.

 

Idea is this company like Bank of America (just an example here) probably had a 1994 era domain controller on a dual core 486 with no active director. Upgraded to NT 4.0 in 1998 merged with a smaller bank in 2000 with Windows 2000 with their own ad. Upgraded to 2003 with forests and bought another company with another 2003 forest with a 2000 era AD ... etc.

 

Long story have a freaking huge global catalog. No biggie

[conna]

How far did you make it?

[binaryzero]

LOL! This was a stupid idea. You do realise that you usually migrate to new servers, than upgrade an existing one. 

Not once have I ever ran an in place upgrade on a domain controller, always built new servers and promoted them to DCs, let replication happen, move FSMO roles, rah rah, decommission old boxes. 

Edited September 12, 2015 by Jared-

[binaryzero]

  On 29/03/2015 at 20:37, Studio384 said:

"should never be used in a real life scenario."

 

I don't know about you, but this is a real life scenario. 100% chance that there is a company out there somewhere that upgraded their server from 3.1 all the way up to 2012 R2, just not in 1 day, but a couple of years. This is a real life scenario, just in turbo speed.

 

No, it's not... 20 year old hardware doesn't run Server 2012 R2. AD didn't exist till Server 2000.