Updating from Windows Server 2003 to 2012

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F1ydave

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Mar 9, 2014
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A little background: I am an accountant who bought out a firm a couple years ago. They had an old file server (RAID 5), which ran fine. It was getting low on space (we all know how well windows does when it gets low). I bought replacement drives that were 2X larger...but couldn't get the server to recognize them as larger. The company who ran his IT and setup that particular HP server couldn't get them to be recognized either. In the end, I virtualized the server as a temporary solution onto one of my old media servers.

Has anyone updated from 2003 (for small business) to 2012 R2? I have tried to follow about 30+ different tutorials and seem to always hit a point where my 2003 is missing the files that are listed in the tutorials, for 2012 R2. I have attempted to use all the 'recommended' software by microsoft. I have done all the recommended updates for the transition too.

I am at my wits end with this crap. I am just not sure how I should go about migrating it. The office runs on this domain with 5 computers plus a printer. Nothing crazy. Any direction would be greatly appreciated.

Would my best bet be to do a backup and restore to 2008 and then to 2012?
 

Mike Bailey

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Sep 24, 2015
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Have you considered simply spinning up a fresh 2012 R2 instance and performing the logical migration of shares from one server to the other?

If it's a simple file server, I can help you figure out what shares exist and how to create them in 2012 R2. It's pretty easy actually.


Doing the migration of the file server role over would only take a small bit of time (a couple of hours, tops) plus any time for the data migration.

Trying to figure out (and make sure it still works) how to upgrade from 2003 to 2012 R2 could end up being a nightmare, as you have already encountered.
 
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F1ydave

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Well, the software was hosted by it, going back to 2004, but I have all the original install files going back that far. I can only hope that the license would work on those. I should be able to backup or even copy the share over to at least have the client files. Worst case scenario is that I leave the old server powered down and available. You never know when the IRS will audit people for 10 years ago, just did 2 last week.

I understand that I would have to duplicate the shares somehow. I am open to giving it a try.
 

Mike Bailey

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I figured there was other software as well. It's very rare for someone to set up a system and go "**** it, it's already there let's install something else as well." I'm sure everyone here has been guilty of this at some point :)

Any idea of what kind of applications run on it? It might be tricky getting them up and running as-is in the new OS environment, particularly if they are legacy apps.

Your best bet may be to spin up a second virtual instance, migrate over the applications + shares that you can, and leave the old VM with what doesn't migrate cleanly. It's a pretty standard thing to do.
 

pricklypunter

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I guess if the applications are critical, you could probably use ThinApp or something to get them running at least, might take some work though depending on what the applications are. Personally, I'm a fan of the clean install, so I would recommend a nice clean 2012 R2 install and configure it for the basics along the same lines as your existing 2003 server. Give it a different IP schema and run it alongside your existing setup until you are confident that you have migrated over everything you need to and got it configured. The larger disks not being recognised is likely a hardware limitation or other, what server is it?
 
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DavidRa

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Are you sure your Windows 2003 server is x64? Most Windows 2003 systems were deployed as x86 and you can't upgrade from x86 to x64, it has to be a clean build (in fact, I seem to remember you can't upgrade x64 directly either you'd have to go via 2008R2 at the minimum).

Normally (and this is the 100,000ft view) you would build a new 2012R2 machine and join the domain, upgrade the schema, then configure as a domain controller and global catalog, then migrate printers, file shares and install software.
 
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cesmith9999

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Mar 26, 2013
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run msinfo32.exe the information on the screen will tell you if the system is running 32 bit or 64 bit.

look for the line listed as system type

Chris
 

F1ydave

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Mar 9, 2014
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Oh yes, it is 32 bit vs 64 bit. Are you saying I can't migrate the domain/active directory, etc because of that? That's why I was looking to just treat it like a file server.

Should I create a new domain with 2012 R2 and join the 2003 to it or vice versa?

Maybe, I could do a clean install of 2003 later on. My new software literally could run of an external harddrive shared on a network. Its based on DOS and is really lite. Really impressive coding from the developers. I am just trying to do this for the old software. My understanding was that I could run legacy in 2012 r2.
 

cesmith9999

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You cannot do a direct upgrade.

In a nut shell, you would have to install a new 2012 R2 server , upgrade your AD schema on 2003, add AD to 2012 R2 join the 2012 server to the domain and then migrate AD to the new 2012 server.

This is not for that faint of heart. you may also need to upgrade to 2008 in the interim. I have not had to do that big of a jump.

BACKUPs are your friend.

You cannot run 16 bit (DOS) apps on a 64 bit OS. you will have to virtualize the app on a 2008 (32 bit) server or win7/8/10

Chris
 

F1ydave

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Mar 9, 2014
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You cannot do a direct upgrade.

In a nut shell, you would have to install a new 2012 R2 server , upgrade your AD schema on 2003, add AD to 2012 R2 join the 2012 server to the domain and then migrate AD to the new 2012 server.

This is not for that faint of heart. you may also need to upgrade to 2008 in the interim. I have not had to do that big of a jump.

BACKUPs are your friend.

You cannot run 16 bit (DOS) apps on a 64 bit OS. you will have to virtualize the app on a 2008 (32 bit) server or win7/8/10

Chris
I already have 2012 R2 host.

I will make a replica of the 2003 and attempt to upgrade the AD schema as you suggested. It it doesnt work, I will look into doing a 2008 upgrade...though this may be difficult. I hope there is a 2008 x86.
 

DavidRa

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You don't want to go to 2008 if you can help it, unless you plan for it to be a temporary stepping stone to 2012. 2008 is already out of mainstream support (most updates), and extended support (i.e. critical and security updates) will be finishing up in a few years.

You have SBS 2003 by the sound of it. You can upgrade the environment, just not the server. I know it's a subtle difference in a small network.

It's also not the sort of thing I'd suggest you tackle without having done it a few times - it's been a number of years since I last did a 2003-2008 or higher upgrade, and there's a lot of moving pieces in the SBS puzzle to consider (Exchange? SharePoint? Remote Access?) - I'd really recommend having someone experienced by your side, but whether that's a paid consultant or a practiced and experienced friend/colleague is a business decision for you to make.

So the 5000 ft view is like this. Note that this procedure is not complete and I take no responsibility for having missed any steps, nor for the results of following this in your environment.

Build a new machine, 2012 R2 (virtual or physical) to be your DC, DNS, DHCP and probably file/print server. Let's call that BUS15-DC (Business name abbreviation, build year 2015, role DC - just my personal naming scheme for this kind of thing). Install the Active Directory, DNS, DHCP, File Server and Print Server roles. On the 2012 media, in the \Support directory (from memory) find the ADPrep folder. Copy that folder to the SBS server, as a user who is Domain Admin, Enterprise Admin and Schema Admin run:
  • adprep32 /forestprep
  • adprep32 /domainprep /gpprep
  • adprep32 /rodcprep
Promote BUS15-DC to a domain controller and GC. Migrate DHCP (with appropriate changes for the new world) and DNS. Create your file shares and shared printers, install old and new drivers, migrate data. Install/migrate applications, test, etc.

That's about ... 50% of the effort. The rest is going to be specific to your environment - drive mappings, shared printers, mail, firewall rules, other functions like VPN/RAS/RWW replacement etc.

Then, decommission the SBS host (remove shares, printers, applications, move FSMO roles to BUS15-DC, demote SBS, clean up DNS, AD Sites and Services etc).
 
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vl1969

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Feb 5, 2014
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I am with Davidra on this one. I just finished my move from sbs 2008 to 2012 and it was not all peachy. So going from 2003 to 2012 will not be smooth. If you already have a 2012 huper v host just build out a vm for ad/dc/dns server, migrate your domain there with all fsmo etc. Build out a vm for file server, than decomision the old dc. If possible build out the vm for a 2003 sbs server that will only host your ups and move the apps there first. This will ensure that you have all of your mission critical apps running on native enviroment on a new hardware than go with the dc and fs move.
 

pricklypunter

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I agree, there is no simple one, two or three step upgrade for you. What you are wanting to do is a real bear to do well, even when you know what you're doing, because there are so many little subtle differences in the way things work between the various server OS. It's a juggling act that I do my utmost to avoid if possible. Some patience, a clean install, a test vlan and a couple of virtual clients usually gets you there much faster with far less stress. Give your new server a good workout after you migrate everything and make sure that all your critical software etc runs as you need it to, them decom the old one :)

It was mentioned earlier about keeping applications that don't play nice with later server OS on the old one being a viable option. I have seen and done exactly that, loads of times, before. Sometimes it's just easier to do this and less costly overall, but it's obviously a decision you would need to make for yourself.
 

F1ydave

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That's what I was afraid of. I am almost done installing a clean server 2003 r2. Im going to see if I can get it over to this one.

Thank you for trying to help guys. Microsoft is just so ridiculous.
 
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vl1969

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Feb 5, 2014
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That's what I was afraid of. I am almost done installing a clean server 2003 r2. Im going to see if I can get it over to this one.

Thank you for trying to help guys. Microsoft is just so ridiculous.
well the only thing you really need to do to begin the transformation is
build out a new VM with same 2003 r2 server but no AD/DC and other domain related stuff on it.
install all the apps you need on it and transfer the config form the old server. if apps are that old, you can try to simply install the app (if all the locations are the same between new and old server.) and copy over the folders from the old server to new overriding the install. (BE VERY CEREFULL, make a backup copy of the new install folder before overwriting it). unless the programs in question store some config in registry or any place other than install folder, they should start and run as if never been moved. once all that is in place, you can build out a file server VM and move all data there. the way I tackled this in my project is using ROBOCOPY to sync the shares to new locations. your new file server on 2012 will have it installed.
create batch script for each main share to copy run it using task manager on new VM , and let it run for couple of days than switch everyone to new shares. if your enviroment is like mine you can go with DFS shares instead. setup a DFS role on the new file server VM . create a dfs namespaces and switch all to them. this way you can give access to old and new locations at the same time and than just remove the old shares as needed. while doing all that you can start building out the new AD/DC vm copy the domain stuff to it when ready and downgrade the old one when done. I have moved like this off a broken DC/AD unit in 2 weeks, totally live with no downtime.
 

F1ydave

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Mar 9, 2014
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Just wanted to say thank you for all your help.

So far so good. I added the 2nd server to the domain and it sure makes the transfering go a lot quicker! :D