1. Alif Ambler

    Hey Steve now that you have a 2008 R2 server and a Windows 7 client, you should try out Direct Access. I am excited to try it but haven’t yet. It is a VPN-less certificate-based way to connect to your ‘corporate’ resources while out of the office.

    Other than a 2008 R2 server and a Win 7 client, I think the only other real requirement is that you have 2 static internet IPs on your server.

    Glad the dc switchover went well. I’ve had 2 go well and one go horribly wrong. I think my problem was more related to renaming the DCs too quickly than the upgrade though….


  2. Kuldip Patil

    My client is having Windows 2000 domain which is containing 1Windows 2000 DC & 2 Windows 2000 ADC he wants to upgrade it to Windows 2008 R2 he start the up gradation but mistakenly he installed windows 2008 Ent. With SP1 & done the schema upgrade (by Forestprep & Domainprep) & he moves the PDC Emulator & Domain Naming master roles to Windows 2008 Ent. Server & also made it to GC. now in that Domain there is one Windows 2008 Ent. server & three Windows 2000 server (on windows 2000 server still having Schema master, Infrastructure Master & RID master roles.)
    Now clients want to install Windows 2008 R2 server in the domain & remove the windows 2000 & windows 2008 Ent. From the domain so please tell me how to go for this.
    Do I need to run forestprep & domainprep again?


  3. Nikosspi

    Hey Steve trying the same thing I could not join the 2008 R2 Server to the 2000 domain with the message “The account is not authorized to log in from this station” after typing username and password to join the domain. Any thoughts?


  4. Hey…
    Am doing exactly the same setup for my client…but I seem not to locate the Adprep32.exe file in the Windows 2008 DVD which makes it impossible for this command to work (adprep32 /forestprep) or should I use the D:\sources\adprep\adprep /forestprep command instead?


  5. Rayden F. Germosen

    This was very helpful. thank you for the wonderful article and simple instructions. I was successful at migrating from w2k to Wk8 following your instructions. I ran into some issues running Adprep /forestprep because exchange 5.5 was installed on the w2k DC but it was corrected by using ADSedit and modifying the exchange attributes.


  6. I was trying to migrate my server from 2000 to 2008R2. When I tried to run addprep I get an error

    Adprep was unable to extend the schema.

    In case that someone get the same error due to the fact that took us 2days to find workarround the problem I give you the links to the solution.

    Your post is the best!!!

  7. George Macdonald

    Thank you for this detailed and well-written article. I was beginning to despair after reading of all the failed attempts and in particular the people who were adamant that a Win2K Server hostname which had an underscore in it just wouldn’t work – my unfortunate circumstance.

    All I did was make sure that the DNS Properties/Advanced tab had “All sames” selected for “Name Checking” in the Win2K Server and then the same for the new Windows Server 2008 R2 DNS as soon as it was up and running. Both systems could see the other as hosts and after I demoted the old system it is still visible as a host, with the underscore intact in its name, and logged into the new domain just fine.

    One thing I’d note is that the new Windows Server 2008 R2 shows as running at “Windows 2000 native functional level” for the forest and the domain. Since I’ll have only that one DC, with server 2008 R2, I assume I’ll want to raise those to 2008 R2 functional level after the Windows 2000 Server, now a member server and still with its underscore in the name, has been retired.

    Thanks again.

    1. George Macdonald

      Sorry to reply to my own post but just a correction, to be clear: that should read “All names” for the “Name Checking” box.

    2. GregW

      Were you able to raise functionality to Sever 2008 functionality mode?

  8. David

    I wish i would have came across this about 90 days ago. I ended up starting the W2k > W2k3 method. Oh well. Great write up.
    To be honest W2k > W2k8 seams much easier than my route.
    Then again i had to do a ton of clean up in AD.
    Either way good stuff.


    1. Ah! Bummer! Sorry you didn’t find this earlier, too! But I’m glad you got it migrated and working. :)

  9. Saad


    Very nice Article.

    One question though , when promoting the server 2008 R2 we have to choose it as a second domain controller and wait for replication to occur before moving FSMO roles .


  10. Kevin Y

    Steve, many many thanks on a great article here! This article worked like a charm for me! I thought that I’d share a couple of additional steps/snags that I worked through that may be of value to future readers:

    – My old W2K server DNS was not set to allow dynamic updates. As a result, DCPROMO on my new W2K8R2 server could not find the domain in question. I had to go into DNS on the old box, allow dynamic updates in the DNS configuration and stop and start the Netlogon service to force to register SRV records in DNS that DCPROMO on the new box was looking for: http://support.microsoft.com/default.aspx?scid=kb;EN-US;241505

    – The domain on my old W2K box was not in Native mode. It was in Mixed mode, which allows for pre-Windows 2000 domain controllers (NT4 I would guess). So I went into the Active Directory Domains and Trust tool on the old W2K box and and set the AD mode to Native.

    Other than the above, promoting in a brand new W2K8R2 DC to my old W2K domain was a piece of cake thanks to your article, and I now have a shiny new DC on my domain. All the best! -Kevin


    1. I had those exact issues, wish i read your comment before googling like a maniac, but i got it working with the same sollution as you posted.

  11. Fransiscus Lesmana

    Hi Steve, thank you for the article.

    If you don’t mind, could you please advise at which point did you rename the new box to the original DC name? Also its IP address?
    I would think it should happen after the demotion of the Windows 2000 server.

    Thank you.


    1. Hi, Fransiscus. I never did rename the new DC or give it the old DC’s IP address. The new DC kept a new name, and new IP. In fact, the old DC is still on my network with its original IP address, and I still use it as a file server. It’s just no longer a DC.

      1. Fransiscus Lesmana

        ah cool. thanks for the reply mate.

  12. Greg

    Steve, Thanks for the great instructions! I’ve been researching for sometime now on how tackle this project. My primary DC is Win 2000 Server SP4 (mixed mode) and I have a Backup DC which is a Windows 2003 Server also acting as Terminal Server. 1) Do I need to demote the Backup DC during this process or just leave it in place until the 2008R2 is ready to be Primary, then demote it? 2) I have the issue of having an _ underscore in my Domain Name, can I leave it or do I really need to fix the domain name and if so, at what point in the process so it doesn’t screw everything up.



    1. Hey, Greg. Hmm… I’m no help with the underscore issue, as I’ve never encountered that. Sorry! But concerning your backup DC, I can’t think of any reason why you’d need to demote it. You don’t need to demote your primary until the very last step, so keeping the backup DC running through the process shouldn’t hose anything either.

  13. James

    This documentation ROCKS!!! Thank you for posting this..


  14. Thank you for the write up Steve. I have a client whose system needs to be upgraded from windows 2000 to windows 2008r2. You’ve saved me some hair. Thanks to those of you who also contributed your work around methods. I’ll report the outcome soon. Thanks again.

  15. Bill

    It just works! Tested on a test network and we had no problems whatsoever.
    Thanks for the information!

  16. Terry

    Hi Steve, I will be doing an upgrade soon from AD 2000 TO AD 08 and need the best possible solution to get it done my environment is like this. we currently have a WAN enviroment with 6 locations and all are connected. we each have a domain controller at each location three has server 2003 and three has windows 2000 server our PDC has windows server 2000 sp 4 on it.
    The three w2k servers cannot be upgraded as they need to be replaced with new servers and that dont seem likely right now no funding. We currently use exchange 2000 for our mail, that will be replaced with a new server. We have purchase two new servers one for the exchange and the other for our new Primary Domain Controller. How do i go about this, will all my domain controllers at each location have to be upgraded to windows 2008 server first before installing my new PDC, and what do i need to do with the exchange box. Its a big undertaking and would love some guidance. Thanks in advance. I have 08 license already.

  17. André

    Can this be achieved for Windows 2012 STD target instead of Windows 2008 R2?

      1. André

        Well. I tried and it doesn´t work for the simple fact that Windows 2012 does not have a adprep32.exe version. It only comes with a 64bit one.

  18. André

    The only issue I had was with the DHCP! I could NOT import the database nor the configuration on the new Win 2008 server.
    It gave me errors regarding conflicting Classes. I don´t remember exactly the error message.


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