Microsoft Windows 2000 & 2003 Domain to Windows 2008 Upgrade Procedure
& Things to Know in General About Server 2008

Prepared by Ian Matthews September 21, 2008, last updated October 6, 2008

Unlike the Server 2003 upgrade process, I have attended no Windows 2003 to 2008 Microsoft presentations (live or on-line).  This is very unusual for Microsoft but the process is easier than it was from 2000 to 2003.

I have now completed five Sever 2008 installs, some on existing domains, some on new domains and I have learned a few things which will make your life easier.  I primarily create this type of documentation for me to use on future installs but I will do my best to not gloss over what I think are easy steps.

NOTE: This process below is offered with no guarantees and we accept no liability. 
To keep an otherwise complex process simple, it is provided in a terse point form.

Windows Server 2000 / 2003 to 2008 Domain Upgrade Process:

PRE-WORK:

1. Set internal DNS servers to "scavenge" every 7 days

   • do this as far before the upgrade as possible: 61+ days preferred but not required

   • this is not a critical step.  Don't let it hold you up if haven't got the time

2. If you are upgrading Window 2000, make sure they are running Service Pack 4 

3. Make sure the servers being upgraded have 1GB of RAM or better (512MB works but it is damn slow).  Click HERE for Microsoft's complete list of official hardware specifications.

4. Make sure the rest of your hardware, software, and BIOS can run Server 2008 by downloading the Microsoft Deployment 2008 Toolkit from HERE.

   • I have installed and run this tool on my 32 bit Vista domain connected PC and then had it check my servers which I planned to upgrade to 64 Bit 2008.  It is easy to use, quick, and provides understandable output.

   • On 2003 there was a great little to "\i386\winnt32.exe /checkupgradeonly" which would tell you all about your situation but 2008 has no such tool built in

   • If you are concerned with your software, you can user Microsoft's searchable 2008 Compatibility Catalog .

5. Note that only "local" (LPR) and "Standard TCP/IP" printer ports work under 2003 and 2008

   • i.e. Lexmark printers using LexLink will have to have their ports recreated

     • this is not true in an upgrade situation (i.e. as opposed to a fresh install) Lexmark ports will likely continue to function even though MS says they won't

6. Flash update EVERYTHING you can; BIOS, FRU/SDR, RAID Controllers...

7. If you are upgrading and existing domain. try to first upgrade has server that has the PDC Emulator and Domain Naming Master & RID Master FSMO's.

   • if these roles are on different computers, upgrade them in the order listed PDC, then DNM, then RID

8. STOP and DISABLE any services you don't need (i.e. the FAX Service, Windows Audio...)

9. Take a backup of your SYSTEM STATE (and everything else, if you can find the time).

   • I use NT Backup for this because it is quick, easy and NEVER lets me down

   • sadly, NT Backup is been replaced in 2008 with some massively limited garbage called Windows Server Backup . 

10. if you are upgrading a print server, and you have 30 minutes, backup your printers using PRINTMIG 3.1 which you can get HERE . 

    • Printer Migrator 3.1 is product is built in Server 2008 (PRINTBRMUI.EXE)

11. set your Domain/Forest to the highest level possible via ACTIVE DIRECTORY DOMAINS AND TRUSTS.  Click the pictures below if you are confused.

    • for the DOMAIN LEVEL, right click on the domain and for the FOREST LEVEL, right click on the FOREST.  Click HERE for more details 

    • you must allow time for these changes to replicate to the other servers on your domain/forest.  For most smaller networks this will be less than 10 minutes, if not instantanious.

    

12. Make sure you have an internet connection on at least one of your network cards because the install process will check for critical updates during the install.

13. IF you have customized Active Directory rules (i.e. Modified Group Policy .ADM file to include blocking of more hard drives than A: B: C: D: [which is available by default] then you need to migrate your Active Directory ADM files to the new ADMX format.  This is a complex area which is fully explained HERE and HERE.

    • Only large enterprises will be concerned with this.  Most companies will skip this step.

14. Reboot and do a common sense check: 

    • resolve any service errors 

    • check for major event viewer errors relating to key AD components like FRS and DNS 

    • verify their is a pile of hard drive space  (like 1GB+)   

   

ACTUAL UPGRADE STEPS:

1. Insert the Windows Server 2008 DVD and go to the \SOURCES folder.  You need to run three Adprep commands (separately but in the order shown) to update the old 2000/2003 schema's to the most current:

   Adprep /forestprep
   Adprep /domainprep
   Adprep /domainprep /gpprep

   • Some of these are fast and some are take some time.  I have not had a failure or error yet so just give it the time it needs to upgrade.

   • If you are planning to upgrade your domain running 32bit Windows to 64bit Windows, you must use 32bit ADPREP (i.e. go get a 32Bit Windows Server 2008 disk, to complete this step.)  If you try to use your 64bit version, not much happens.

   • You can not a "Upgrade Server 2003 32 Bit to Server 2008 64 Bit".  You must do a bare metal install.

   • If you do have ADPREP weirdness or errors, you will find THIS useful. 

   • Under older operating systems, it used to be that you had a week to complete your upgrade to the new Operating System but I have not been able to confirm on deny this is still the case

2. If you want to the option to have a cool new Server 2008 feature called a READ ONLY DOMAIN CONTROLLER, you must also run the following:

   Adprep /RODCPREP

   • If you don't know what an RODC is, click HERE.

3. If you choose not to follow step two (which I usually skip) will see the following error message which you can safely ignor during the install process:
   
   

4. Force replication to all DC's via Active Directory Sites & Services and then wait a MINIMUM of 20 minutes before starting the Windows 2008 upgrade.  If you did not wait long enough you will see the following error message:
   
   

5. Disable all anti-virus and non-windows applications like event log trackers and 3rd party FTP servers

• SQL2000/2005 services do NOT need to be shut down

6. IF YOU ARE UPGRADING: insert the W2008 DVD, let it autoplay, and select INSTALL then Upgrade
   IF YOU ARE INSTALLING ON A FRESH SERVER:  Boot off the W2008 DVD and answer the obvious questions

   • complete the upgrade process which will take less than an hour for most modern server

   • No, you will NOT be asked for a "CD KEY".  You will have to enter the key AFTER the install is complete as part of the "activation" process.  See the end of THIS if you want more information.

   • You may see "This computer has dynamically assigned IP address(es)..." relating to your network configuration.  Personally, I disabled IP v6 along with all unused Network Cards, then set static IP's on the only in-use cards but still had this message.
     
     

   • You will almost certainly see "a delegation for this DNS server cannot be created because the authoritative parent zone cannot be found...".  I understand this has to do with rDNS (reverse lookups) but my servers have rDNS configured and I still see this error.  This can be safely ignored.
     
     

7. After you have completed your install, you will be presented with the Initial Configuration Wizard.  You should click on and set, ALL five items in section 1 and 2. There are some important things to note:
   

   • I strongly recommend you approve sending Automatic Feedback

   • I strongly recommend you NOT approve Automatic Updating.  You should choose, "Automatically download but do NOT install". 

     • If you choose the default setting of "Automatically Download and Install Updates", your server WILL reboot itself sometime after 3am when updates are complete.  Not to mention that YOU should be in control of your servers updates, not Microsoft.  I recommend you wait 2 weeks after release before you install server updates; this gives Microsoft enough time to correct or remove "bad" patches. 

   • You should check for and install all Windows Updates immediately

8. After the upgrade is complete, check event viewer for key errors - ignore Event ID 1931    

9. Check DNS and AD replication

   • i.e. add a new user on one server and see if it shows up on the other DC's 

10. Check DEVICE MANAGER (which is now under SERVER MANAGER, DIAGNOSTICS, DEVICE MANAGER) to confirm all of your hardware is functional under Server 2008.

11. Unlike its predecessors, Server 2008 does not have "Support Tools" (from the DVD) or a "Resource Kit" so you have nothing extra to install.

12. Unlike its predecessors, you do not have to copy the install files from the DVD to a directory on your server (i.e. the i386 directory) on Server 2008.  Like Vista, the install files are stored in the Windows\WinSXS folder  

13. You will need to go to System Properties to manually activate Server 08. 

    • Be sure to click CHANGE PRODUCT KEY and enter your real key.

14. Re-enable Antivirus and another of 3rd party services disabled before the upgrade 

15. Perform your usual system maintenance routine like deleting temp files and old profiles, emptying the Recycle Bin...

16. Most sub 500 seat companies will want to enable Automatic Defragmentation.  To do this just click START and type DEFRAG in the search bar and do what is obvious.
    

17. Most companies will want to spend the 10 seconds to enable Shadow Copies (if they are not already enabled) by right clicking on any drive and selecting the Shadow Copy tab.
    

    • I am astounded at how many IT "Professionals" either don't use or don't know about Shadow Copies.  They are SOOOOO easy to setup and use.  They will save you many many hours performing tape restores.  Read THIS if you want more details

    • Server 2008 includes the ability to revert an entire partition to a PREVIOUS VERSION state
      

18. Repeat the relevant steps for all DC's

19. After all DC's are upgraded, increase "Functional Mode" via Active Directory Domains & Trusts to 2008 NATIVE MODE.  See Step 11 in PreWork near the top of this page.

• You can/should read about the 2008 Windows Recovery Environment at the bottom of THIS page.

• If you ran IIS 5 or 6, you are in for a surprise... lots of changes:

  • The old FTP is still available as a ROLE FEATURE under IIS but there is a new FTP for IIS7 from Microsoft you can download HERE and read about HERE.
    

• Front Page Server Extensions (FPSE) and Share Point Team Services update are GONE.

  • You will likely want the new WEBDAV which allow you to have FrontPage or Sharepoint Designer (or most other web development tools) connect to and modify your sites via FILE, OPEN SITE. 

  • WebDav 2008 was released after Server 2008 was released so you need to download it separately which you can do HERE .

  • A really simple read on how to configure WebDav is HERE.

  • There is an UNSUPPORTED version of FPSE for 2008 which Microsoft commissioned.  Have I mentioned it is UNSUPPORTED and will NOT exist in the next version of Windows Server.

• Remote Desktop's "Console Mode" has changed to /ADMIN mode.  Click HERE for details.