Transitioning your Active Directory to Windows Server 2008

You might be running Windows Server 2003 and Windows Server 2003 R2 Domain Controllers at the moment and you’re looking to replace these servers with Windows Server 2008 Domain Controllers to utilize the new features of Windows Server 2008. You might also be looking to replace your aging Windows Server 2003 and Windows Server 2003 R2 Domain Controllers with spanking new Windows Server 2008 Domain Controllers, while keeping your Active Directory running smoothly.

This post intends to help you with this transition in a structured, balanced and thorough way and describes:

  • Choosing between In-place upgrading, transitioning or restructuring
  • Reasons to transition to Windows Server 2008
  • Steps to transition
    • Prepare your Active Directory environment
    • Installing the first Windows Server 2008 Domain Controller
    • Installing additional Windows Server 2008 Domain Controllers
    • Taking care of Flexible Single Master Operations and Global Catalogs
    • Checking proper installation and replication
    • Demoting Windows Server 2003 Domain Controllers
    • Raising the domain functional level
    • Raising the forest functional level
  • Concluding

 

Ways to migrate

Upgrading your Windows Server 2003 Active Directory environment to Windows Server 2008 can be done in three distinct ways:

  • In-place upgrading
    Windows Server 2003 and Windows Server 2003 R2 can both be upgraded in-place to Windows Server 2008, as long as you keep the following in mind:

    • The Windows Server 2003 patchlevel should be at least Service Pack 1
    • You can’t upgrade across architectures (x86, x64 & Itanium)
    • Standard Edition can be upgraded to both Standard and Enterprise Edition
    • Enterprise Edition van be upgraded to Enterprise Edition only
    • Datacenter Edition van be upgraded to Datacenter Edition only

In-place upgrading requires you to run adprep.exe before starting the upgrade process on the Domain Controllers. Check the information provided by Jorge for more information.

  • Transitioning
    Migrating this way means adding Windows Server 2008 Domain Controllers to your existing Active Directory environment. After successfully moving the Flexible Single Master Operations (FSMO) roles you can simply demote the previous Domain Controllers, remove them from the domain and throw them out of the window.Transitioning is possible for Active Directory environments which domain functional level is at least Windows 2000 Native.
  • Restructuring
    A third way to go from Windows Server 2003 Domain Controllers to Windows Server 2008 Domain Controllers is restructuring your Active Directory environment. This involves moving all your resources from one (Windows Server 2003) domain to a new and fresh (Windows Server 2008) domain. Using tools like the Active Directory Migration Tool (ADMT) are priceless in these kind of migrations.

 

Reasons to transition

I feel transitioning is the middle road between the two other ways to migrate to Windows Server 2008:

  • Restructuring means filling a new Active Directory from scratch
  • In-place upgrading means you’re stuck with the same hardware and limited to certain upgrade paths
  • Transitioning means you get to keep your current Active Directory lay-out, contents, group policies and schema. Transitioning also means moving to new machines, which can be dimensioned to last another three to five years without trouble.

Transitioning is good when:

  • You worked hard to get your Active Directory in the shape it’s in.
  • Your servers are faced with aging.
  • In-place upgrading leaves you with an undesired outcome (for instance 32bit DC’s)
  • You need a chance to place your Active Directory files on different partitions/volumes.

When done right your colleagues might not even suspect a thing! The downside is you need to know exactly what you’re doing, because things can go wrong pretty fast. that’s why I wrote this post.

 

Steps to transition

Transitioning to Windows Server 2008 Domain Controllers consists of the following steps:

Before you begin

Avoid common mistakes

There is a very good Microsoft Knowledge Base article on Common Mistakes When Upgrading a Windows 2000 Domain To a Windows 2003 Domain, written by community experts.  I suggest you read it. (twice) Most of the contents also apply to transitioning from Windows Server 2003 (R2) to Windows Server 2008

Plan your server lifecycle

It’s not uncommon for a Domain Controller to sit on your network for a period of five years. I believe you should take this in mind when selecting and buying a server. You should plan your partitions (or volumes) carefully and place the Active Directory files on separate volumes when your needs justify it. The Windows Server catalog helps you pick systems that will run Windows Server 2008 with ease.

Assess your readiness

Microsoft has kindly provided a tool to scan systems to assess whether systems are capable of running Windows Server 2008, whether drivers are available (either from Microsoft update or on the installation media) and what problems you might encounter when deploying Windows server 2008. I recommend checking your systems with this tool, which is called the Microsoft Assessment and Planning Solution Accelerator (MAP for short).

Backups

Make backups of all your Domain Controllers and verify you can restore these backups when needed.

Documentation

It is a good thing to know exactly what you’re migrating. When things go wrong you might need to be able to revert back to the old situation. This might require the Directory Services Restore Mode (DSRM) password and credentials for service accounts, which might not be written down anywhere. In multiple Domain Controller, multiple domain, multiple forest and multiple sites scenarios it’s very wise to make a table containing the relevant information per Domain Controller in terms of Flexible Single Master Operations (FSMO) roles, Global Catalog placement, domain membership, site membership, replication topology, routing tables, IP addressing, etc.

Communication

When done right your colleagues might not even suspect a thing, but it’s important to shed some light on what you’re doing. (Make someone) communicate to the end users that you’re going to mess with the core of their infrastructure. This might result in colleagues understanding you’re (really) busy and might also result in problems being reported fast. Both are good things if you’d ask me…

 

Prepare your Active Directory environment

Before you can begin to introduce the first Windows Server 2008 Domain Controller into your existing Active Directory environment, you first have to prepare the Active Directory.

Microsoft provides a tool called adprep.exe to facilitate this preparation. You need to run the following commands on the following servers in your Active Directory environment:

Command Domain Controller
adprep.exe /forestprep Schema Master
adprep.exe /domainprep Infrastructure Master
adprep.exe /domainprep /gpprep Infrastructure Master
adprep.exe /rodcprep * Domain Naming Master

* Optional when you want to deploy Read Only Domain Controllers.

After preparing your Active Directory for Windows Server 2008 be sure to check the process. Breadcrumbs to failures may be found in the event viewer, but real men will check the adprep.log files. If your life depends on it, you can use the HowTo Jorge wrote to check forestprep and domainprep succesfully replicated to all Domain controllers.

Allow sufficient time for proper replication to all Domain Controllers. (In large environments with specific replication needs this might take hours.) When you feel all changes have been replicated use the replmon and repadmin tools to check and optionally troubleshoot Active Directory replication.

 

Install the first Windows Server 2008 Domain Controller

You could already start installing Windows Server 2008 on a fresh box and make it a member of the domain, while preparing your Active Directory. When you’re done preparing your Active Directory you can safely go ahead installing the first Windows Server 2008 Domain Controller by promoting a Windows Server 2008 box to a Domain Controller, using dcpromo.exe.

When running dcpromo.exe make sure you select to make this Domain Controller an extra Domain Controller for the Active Directory domain you’re transitioning. Type a secure password for Directory Services Restore Mode (DSRM).

Tip:
Write down the the Directory Services Restore Mode (DSRM) password.

Since each Active Directory Domain Controller stores a copy of the Active Directory information, like users, computers, etc. and the NETLOGON and SYSVOL shares, your new Windows Server 2008 Domain Controller will be open for business after you restarted it to complete the wizard.

 

Install additional Domain Controllers

Installing additional Windows Server 2008 Domain Controllers is as easy as purchasing them, licensing them, installing them and promoting them. There’s really nothing to it: Once you’ve introduced the first Windows Server 2008 Domain Controller you know how to do it.

If you find installing loads of Domain Controllers is a tedious job you might want to promote servers to Domain Controllers using answer files. When Domain Controllers need to be placed in locations with limited connectivity or bandwidth constraints you might want to explore the Install from Media (IFM) possibilities.

 

Take care of FSMOs and GCs

Using the Active Directory Sites and Services MMC Snap-in make new Windows Server 2008 Domain Controllers Global Catalog servers appropriately.

Also transfer Flexible Single Master Operations (FSMO) Role to appropriate servers. You can use the Graphical Interface to move the Flexible Single Master Operations (FSMO) from your Windows Server 2003 servers to Windows Server 2008. Another option is using ntdsutil.

In multiple Domain Controller scenarios Jorge has a good rule of thumb on Global Catalogs and the Infrastructure Master Flexible Single Master Operations (FSMO) Role. Either:

  • Don’t make the Domain Controller holding the Infrastructure Master Flexible Single Master Operations (FSMO) Role a Global Catalog server, (and only) if there is another Domain Controller in the same Active Directory domain that is also not a Global Catalog;
  • Make all Domain Controllers Global Catalog servers.

When your environment includes Microsoft Exchange Server reboot a Domain Controller after making it a Global Catalog server. Microsoft Exchange communicates with Active Directory through Global Catalogs using MAPI. Although the Active Directory Sites and Services MMC Snap-in doesn’t ask for it you need to restart a Domain Controller at least one time after making it a Global Catalog before it starts talking MAPI.

Make sure your Windows Server 2003 Domain Controllers are no longer clinging on to any of the Flexible Single Master Operations (FSMO) Roles using the graphical user interface, using replmon or the following command using netdom.exe from the Resource Kit:

netdom.exe query fsmo

 

Check proper installation and replication

It is a best practice to review the logs to identify any problems that might have occurred during the promotion. The logs to scrutinize specifically are:

  • dcpromo.log
    All the events regarding the creation and removal of Active Directory, SYSVOL trees and the installation, modification and removal of key services
  • dcpromoui.log
    all the events from a graphical interface perspective

Also check the event viewer.

Allow sufficient time for proper replication to all Domain Controllers. (In large environments with specific replication needs this might take hours.) When you feel all changes have been replicated use the replmon and repadmin tools to check and optionally troubleshoot proper Active Directory replication.

 

Demote Windows Server 2003 Domain Controllers

I’ve seen Domain Controllers became the prostitutes of the server room in many environments. Any software that didn’t require a dedicated server or was deemed highly dependent on the Active Directory was installed on the Domain Controller. When you’re one of the administrators treating their Domain Controllers like that you’re going to have a hard time demoting your Domain Controllers. Testing demotions in a separate (virtual) testing environment could give your a clear picture on the behavior of your Windows Server 2003 ex-Domain Controllers though!

From my personal experience I can tell you it’s not recommended to demote a Domain Controller when it has Exchange Server or Internet Information Services installed after it was promoted. You’re going to have to find another box to install these services on.

When your Windows Server 2003 Domain Controllers are also Domain Name System (DNS) servers it is recommended to change the DNS zones into Active Directory Integrated DNS zones (when possible) so they get replicated to any Domain Controller running the DNS service. Installing the DNS Server role on a Windows Server 2008 would then suffice to migrate DNS settings. Be sure to change the DNS information on your other servers and workstations, before removing DNS servers from your network.

You can safely demote a Domain Controller using the dcpromo.exe command. If you’re unsuccessful you might want to try to remove the server from Active Directory the hard way, which Jorge describes. (leaving out the percussive maintenance option though)

 

Raise the domain functional level

After you’ve successfully demoted the last Windows Server 2003 Domain Controller for a specific domain (or you don’t feel the need to ever add pre-Windows Server 2008 Domain Controllers to your Active Directory environment) you’re ready to raise the Domain functional level of that domain.

Upgrading the domain functional level to Windows Server 2008 adds the following features to your environment:

  • Distributed File System Replication (DFS-R) support for SYSVOL, which provides more robust and detailed replication of SYSVOL contents with minimal replication traffic compared to FRS.
  • Advanced Encryption Services (AES 128 and 256) support for the Kerberos protocol.
  • Last Interactive Logon Information, which displays the time of the last successful interactive logon for a user, from what workstation, and the number of failed logon attempts since the last logon.
  • Fine-grained password policies, which make it possible for password and account lockout policies to be specified for users and global security groups in a domain, instead of per domain only.

Note:
Raising the functional level is a one way procedure. Once you’ve raised your domain functional level there’s no way to return to the previous domain functional level.

Raising the domain functional level in Windows Server 2008 looks remarkably similar to raising the domain functional level on Windows Server 2003:

  1. Log on to the Domain Controller holding the PDC emulator FSMO role with a user account that is a member of the Domain Administrators group..
  2. Open Active Directory Domains and Trusts.
  3. In the console tree, right-click the domain for which you want to raise functionality, and then click Raise Domain Functional Level.
  4. In Select an available domain functional level, click Windows Server 2008, and then click Raise.

 

Upgrade the forest functional level

After you’ve successfully upgraded the domain functional level of all the domains in your Active Directory forest you’re ready to upgrade the Forest functional level. This will not add any features, but will result in all domains that are subsequently added to the forest will operate at the Windows Server 2008 domain functional level by default.

Note:
Raising the functional level is a one way procedure. Once you’ve raised your forest functional level there’s no way to return to the previous forest or domain functional levels.

To upgrade the forest functional level to Windows Server 2008 perform the following actions:

  1. Log on to the Domain Controller of the forest root domain holding the PDC Emulator FSMO role with a user account that is a member of the Enterprise Administrators group.
  2. Open Active Directory Domains and Trusts.
  3. In the console tree, right-click Active Directory Domains and Trusts, and then click Raise Forest Functional Level.
  4. Under Select an available forest functional level, click Windows Server 2008, and then click Raise.

 

Concluding

Transition your Active Directory to Windows Server 2008 seems as easy as running adprep and installing Windows Server 2008 Domain Controllers. It might be in small shops with one single Domain Controller in one single Active Directory domain in its own forest with one single Active Directory site.

Be sure to check whether what you’re doing is successfully installed, performed and replicated before you screw up your Active Directory environment though!

Further reading

WS2008: Upgrade Paths, Resource Limits & Registry Values
Common Mistakes When Upgrading a Windows 2000 Domain To a Windows 2003 Domain
Win Server 2008 Directory Services, Functional Levels Overview
Functional Levels In Windows Server 2008 Part I
Functional Levels In Windows Server 2008 Part II
Appendix of Functional Level Features
Active Directory Installation and Removal Issues
Using Ntdsutil.exe to transfer or seize FSMO roles to a domain controller
Using Repadmin.exe to troubleshoot Active Directory replication
HOW TO: Use the Replication Monitor to Determine the Operations Master and GC Roles
HOW TO: troubleshoot intra-site replication failures
Windows Server 2008 dcpromo Changes
Active Directory Domain Services: UI changes – Part 1
Active Directory Domain Services: UI changes – Part 2
How to raise domain and forest functional levels in Windows Server 2003
FSMO placement and optimization on Active Directory domain controllers
How to optimize Active Directory replication in a large network

13 Responses to Transitioning your Active Directory to Windows Server 2008

  1.  

    I love your work. Thanks for providing such an well structured summary.

  2.  

    Thanks, Sander.
    It works excellent. I checked adprep.log-s, saw in event viewer – OK, active directory is replicated.
    Now I have 2 servers: 2003 & 2008.
    2008 has only AD and empty. I gonna put shared folders with data and sites here(2008) from 2003 and throw it away.
    So, how can I do it best?
    Is it rigth: At nigth, copy all data and re-create shared folders on the new server, swicth off 2003 and rename 2008 to 2003-name?
    And what would be with users, which synchronize their data with server?

  3.  

    I think the File Server Migration Toolkit (FSMT) is an excellent tool to migrate your file shares from the Windows Server 2003 box to the Windows Server 2008 box. (version 1.1 with Windows Server 2008 is currently in beta)

    Migrating users with Offline files will be more tricky, but CSCCMD.EXE can help you out there. Check out Microsoft Knowledge Base Article 884739.

  4.  

    Dankie, Sander.

    I have another question about AD, I’ve put it here because I did not find proper thread in your blog and I didn`t find an answer in Microsoft site.

    There is a picture of my AD computers:

    http://img7.imagevenue.com/img.php?image=71405_AD_122_1034lo.jpg

    So, some computers are lost (like DSK0008, DSK0009 …). It was since previous 2003 server crash – nobody saved AD, then AD was created from the beginning, some computers were just rejoined to the domain, others not. Those users which are not rejoined still can log on, but I see the event on the server:

    Event ID:    5513

    Source:      Netlogon

    Description: The computer name <computer name> connected to server <name>

                using the trust relationship to the <name> domain. However,

                the computer doesn’t properly know the security identifier

                (SID) for the domain. Reestablish the trust relationship.

    The problem is: I can simply rejoin those computers(Microsoft’s answer). But in this case I would have so much problems – because new profile will be created and I must move all staff and mail and funny things… on each computer. And speak with blond girls and explain them things …

    So, is there a way to restore those “trust relationships” between computers and new 2008 server without troubles?

  5.  

    Yeah, sure!

    The only problem you seem to be experiencing is the loss of user profiles. (which are actually not lost)

    I’ll assume you’re the one changing the domain membership of the computer and you don’t have any roaming profiles.

    After you’ve made the workstation a member of the new domain and after the user has logged on and off once, you can log in as an administrator and copy the contents of the old profile in C:\Documents and Settings\UserName to the new profile in C:\Documents and Settings\UserName.DomainName. (check datestamps to determine the old and new profile)

    This will restore the user profiles. Now you can ask these blond girls meaningful questions instead of merely fixing their computer troubles Cool

  6.  

    Hello Sender again.

    So, step by step and with your BIG help I do things.

    The next is a spare Windows Server 2008 problem:
    I bought second server to make it spare. I plan to copy (automatic replication) AD on it only for emergency. If first server crashes – users can logon using another one. I can quickly restore data from backup, …

    But when I try to install AD on it using dcpromo.exe – in the last stage (installing) it says funny thing:

    “No mapping between account names and security IDs was done.”

    Microsoft KB answers everything but this. So, do you know the reason?

    P.S. When adjust setting in dcpromo I use: logon of domain administrator and password, check “Add to existing domain”, Global Catalogue.

  7.  

    You can use the HowTo Jorge wrote to check forestprep and domainprep succesfully replicated to all Domain controllers.

    Update for Win 2008 adprep:

    Check for a successful Forest Update:

    repadmin.exe /SHOWOBJMETA * “CN=ActiveDirectoryUpdate,CN=ForestUpdates,CN=Configuration,DC=domain,DC=com”

    Check for a successful Domain Update :

    repadmin.exe /SHOWOBJMETA * “CN=ActiveDirectoryUpdate,CN=DomainUpdates,CN=System,DC=domain,DC=com”

  8.  

    O boy, this is EXACTLY what I was looking for! Thanks for a well thought out and structured outline.

    I feel a bit better now that I read this. Messing with AD is not something for the faint-of-heart.

    I have had the Win 2008 DVD sitting around gathering dust long enough.

    Bill

  9.  

    Where will you run the adprep? is it form the source or destination server.

    When i’m trying to run adrep from win2k3 server(source) i got an error. i’m running adprep from the i386 sp2 which i extract from .exe

    it says that i cannot run it from there

    ————————————————

    Adprep was unable to copy file C:\win2k2sp2\i386\dcpromo.cs_ from installation p

    oint to local machine under directory C:\WINDOWS\system32\debug\adprep\data.

    [User Action]

    Check the log file Adprep.log in the system root System32\Debug\Adprep\Logs dire

    ctory for more information.

    Adprep encountered a Win32 error.

    Error code: 0x2 Error message: The system cannot find the file specified..

    Adprep was unable to copy setup files from installation point to local machine.

    —————————————————-

    thank you…

  10.  

    You should run adprep on the Domain Controllers holding the respective FSMO roles. These are your current Windows Server 2003 Domain Controllers.

    I recommend using adprep from the sources\adprep folder from either a Windows Server 2008 DVD or Windows Server 2008 with integrated Service Pack 2 DVD. Be sure to use DVD media corresponding to the architecture (x86 or x64) of your Windows Server 2003 Domain Controllers. You can use trial media of Windows Server 2008 for this purpose, if need be.

    Also, when you copy adprep to a local folder on your Domain Controller, be sure to copy the whole folder containing adprep.exe and not just adprep.exe itself.

  11.  

    Do you have any links to any articles on moving/migrating from an existing domain, i.e. thedomain.com to a new one, i.e. thenewdomain.com? I basically want a fresh domain but need to migrate or move all existing servers & clients to the new domain, including exchange and app servers.

    Hoping to find an article that at least outlines all the areas to consider so I don’t screw it up!!

  12.  

    Hi chudless,

    Thanks for your reply.

    I don’t have a blogpost in this series on the ‘migrating’ scenario. Huge differences between networking environments and their impact on the migration process make that an impossible blogpost to write.

    Microsoft has an extensive 267-page Word document, detailing how to use the Active Directory Migration Tool (ADMT) to perform the type of migrations you describe.

    Note:
    Although the downloadpage talks about version 3.0 of the tool, the documentation applies to version 3.0, 3.1 and version 3.2.

    Note:
    ADMT versioning is not about bugfixes, but about the support matrix of the source and target domains/forests. Later versions of ADMT support more recent Windows Server OS’s and Functional Levels as target domains and forests, but also limit the Windows Server OS’s and Functional Levels as source domains and forests.

    Good luck!

  13.  

    Thank you very much for such a wonderful detailed information.

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