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Windows Server : Planning for Migration, Upgrade, and Restructuring

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Although it is possible to add a member server running Windows Server 2008 to an existing Microsoft Windows Server 2003 domain, at some point in your organization’s migration to Windows Server 2008, you are going to want to upgrade your organization’s domain controllers (DCs).

Migration Paths

You can take one of three general paths to move from an existing Active Directory environment to an AD DS environment. An AD DS environment is another way of indicating a domain that has Windows Server 2008 DCs. These paths are known as the domain upgrade, the domain restructure, and the upgrade-then-restructure. When planning which method to use, consider factors such as the amount of time the migration should take and the availability of new server hardware.

Domain Upgrade Migration Path

The domain upgrade migration path involves upgrading the operating system of a Windows Server 2003 DC to Windows Server 2008 or installing Windows Server 2008 DCs into a Windows 2000 Server or Windows Server 2003 domain. Unlike Windows Server 2003, which you can configure to support domains that use both Microsoft Windows NT 4.0 and Windows Server 2003 DCs, Windows Server 2008 DCs cannot coexist in the same domain as Windows NT 4.0 primary and backup DCs. Therefore, if you are planning to add Windows Server 2008 DCs to a domain, you need to ensure that domains in your organization are at the Windows 2000 Native functional level or higher. Domains at the Windows 2000 mixed or Windows Server 2003 interim functional level do not support Windows Server 2008 DCs. There is no direct upgrade path between Windows NT 4.0 and Windows Server 2008. Plan to use the domain upgrade migration path when you will not have access to a significant amount of new server hardware on which to install new deployments of Windows Server 2008.

Domain Restructure Migration Path

The domain restructure migration path involves copying Active Directory objects from the original domain or forest to the new Windows Server 2008 domain or forest, using tools such as the Active Directory Migration Tool, covered later in this lesson. After all objects are migrated, the DCs in the original domain or forest are decommissioned or redeployed. The domain restructure migration path includes the following advantages:

  • The original environment remains the same until the migration is completed. Users are not forced to the new environment until it is tested and ready.

  • It enables the selective migration of objects. When you perform a domain upgrade, all objects are upgraded, including those that are redundant, inactive, and no longer necessary. Domain restructure migrations enable organizations to clean up their environments as they transition to the new technology.

The domain restructure migration requires you to have enough new server hardware to support both the original and destination environments concurrently. If the budget does not allow for new server hardware, the domain upgrade migration path is a more feasible alternative. Although it is possible to perform a domain restructure migration using virtualization, you should avoid this approach unless you are planning an AD DS deployment that primarily involves virtualized DCs.

Upgrade-Then-Restructure Migration Path

The upgrade-then-restructure migration path, also known as a two-phase migration, involves upgrading the original domain or forest and then migrating Active Directory objects to a new Windows Server 2008 domain or forest. This process essentially combines the domain upgrade and domain restructure approaches, enabling an organization to benefit immediately from a Windows Server 2008 upgrade and then to transition to new Windows Server 2008 DC hardware at some point in the future, with the added benefit of removing unnecessary Active Directory objects through the selective migration process.

Active Directory Migration Tool

You can use the Active Directory Migration Tool v3.1 (ADMT v3) to migrate Active Directory objects within a forest for domain consolidation or to migrate objects to another forest for interforest migration. You can use the ADMT to migrate users, groups, service accounts, computers, and trusts. The ADMT has a simulation mode that enables administrators to evaluate the results of planned migrations prior to performing the actual migration.

More Info: Obtain the Active Directory Migration Tool

You can obtain the Active Directory Migration Tool from the Microsoft Web site at http://go.microsoft.com/fwlink/?LinkID=75627.


Upgrading an Existing Domain to Windows Server 2008

There are two basic strategies for transitioning from an existing domain to a Windows Server 2008 AD DS domain. The first strategy is to introduce new Windows Server 2008 DCs into the forest and then either to retire or upgrade existing Windows 2000 Server or Windows Server 2003 DCs. The second strategy is simply to perform an in-place upgrade of all existing Windows Server 2003 DCs. Both of these strategies are useful when pursuing the domain upgrade migration path.

Preparing the Environment

You need to perform several steps prior to adding a Windows Server 2008 DC to an existing Active Directory environment, even if you do not intend to change the current domain or forest functional level. These steps include ensuring that existing DCs in the environment have appropriate patches and service packs installed and that the Active Directory schema has been appropriately prepared for the introduction of Windows Server 2008 DCs.

If you are planning to add a Windows Server 2008 DC to a domain that has active Windows 2000 Server DCs, which is possible when using the Windows 2000 Native domain and forest functional level, you must ensure that all Windows 2000 Server DCs have Service Pack 4 and hotfix 265089 installed.

To prepare a forest for the installation of a read-only DC (RODC), run the adprep /rodcprep command on the schema master. This command needs to be run only once on the schema master and does not need to be run in each domain in the forest in which you intend to install Windows Server 2008 RODCs. As is the case with adprep /forestprep, to execute this command successfully, the user account must be a member of the Enterprise Admins, Schema Admins, and Domain Admins groups. From a planning perspective, consider running adprep /rodcprep immediately after running the adprep /forestprep command even if you have no immediate plans to deploy RODCs in your environment. If, in the future, it becomes necessary to deploy RODCs in the enterprise, the deployment will be able to proceed without problems that might occur if future administrators do not check whether the forest has been prepared for the deployment of RODCs prior to attempting deployment.

More Info: Microsoft Exchange 2000 Server and Windows Services for UNIX 2.0

Known compatibility problems exist between adprep.exe and Exchange 2000 Server and Windows Services for UNIX 2.0 where these products have been deployed in Windows 2000 Server domains. Consult KB article 314649 to resolve the Exchange 2000 Server issue and either install the Q293783_sfu_2_x86_en.exe hotfix for Windows Services for UNIX 2.0 or upgrade to Windows Services for UNIX 3.0.


After you have completed the forest-level preparation tasks, you must still perform preparation on a per-domain basis before you can install Windows Server 2008 DCs. A user who is a member of that domain’s Domain Admins group must run the adprep /domainprep /gpprep domain preparation command on the DC that holds the infrastructure master role. After this command has been run, Windows Server 2008 DCs can be introduced to that domain.


In-Place Domain Controller Upgrade

Upgrading each DC in the domain from Windows Server 2003 to Windows Server 2008 works well within the limitations of the types of upgrades you can perform. For example, you cannot upgrade a computer that has Windows Server 2003 Enterprise to Windows Server 2008 Standard, and you cannot upgrade any Windows Server 2003 DC to a Windows Server 2008 DC that is running the Server Core installation. Before performing an in-place upgrade of a Windows Server 2003 DC, ensure that Service Pack 1 (SP1) or later has been applied. This does not apply to Windows Server 2003 R2 DCs, which are effectively updated to SP1 when initially deployed.

Quick Check

1.On which DC should you perform the first forest preparation task?
2.Which of the Windows Server 2003 domain functional levels do not support the introduction of Windows Server 2008 DCs?

Quick Check Answers

1.You must run adprep /forestprep on the DC hosting the schema master role.
2.Windows 2000 Mixed and Windows Server 2003 interim domain functional levels support Windows NT 4.0 DCs. There must be no Windows NT 4.0 DCs in a domain if a Windows Server 2008 DC is to be introduced.

Cross-Forest Authentication

Enterprise-scale organizations often deploy multiple forests. Although these forests are usually designed for separate divisions within the enterprise, a level of integration between these separate network environments is often required. The most common way of allowing users in one forest to access the resources located in another is to configure an interforest trust so that any user in any domain in the trusted forest can access any resource in any domain in the trusting forest. An alternative is an external trust that exists between specific domains in different forests rather than in any domain in each forest. 

When planning a trust, you must consider the following factors:

  • Should the trust be bidirectional or one-way?

  • Is it necessary to use selective authentication?

  • Is it necessary to implement Security Identifier (SID) filtering?

When planning trust direction, ensure that you grant only the minimum required access needed to meet business requirements. This might mean using external trusts rather than forest trusts. Remember that two-way trusts are required only when users in each forest or domain need access to resources located in the other forest or domain. If an organization uses a resource forest scenario, it is necessary to configure only a one-way trust from the forest that hosts accounts to the forest that hosts resources.

You can limit trusts by using selective authentication, which restricts the number of users in the trusted forest who are able to access shared resources in the trusting forest. If you deploy forest-wide authentication rather than selective authentication, any user authenticated over an interforest trust will be assigned the Authenticated Users SID for the trusting forest, essentially granting users from a trusted forest almost all the default rights that users in the trusting forest have. The benefit of selective authentication is that it limits the groups of users who are able to access resources across the trust and enables you to limit which computers in the trusting forest can be accessed across the trust. You can configure selective authentication when you first create the trust or alter the properties of an existing trust as shown in Figure 1. If you choose not to implement selective authentication, plan to remove the Authenticated Users group from all sensitive resources in the trusting domain.

Figure 1. Configuring selective authentication


SID filtering prevents users from using SIDs stored in the SIDHistory attribute when accessing resources in a trusting forest. The SIDHistory attribute exists to support the migration of user and group accounts between domains and allows the user accounts to access resources in their original domain during the migration process. A new SID will be assigned to the account when it is moved to the new domain, and that new SID will not be assigned access to the resources that are yet to be migrated from the original domain. SID filtering can block the SIDHistory attribute across the forest trust, which ensures that accounts that have been migrated to a trusted forest no longer have access to resources in the original forest unless explicitly specified. When enabled, any SIDs from domains other than the trusted domain are ignored. For example, SID filtering is enabled by default on any trust created using a computer running Windows Server 2008. Disable SID filtering only during the migration of user and group accounts from one forest to another. This allows access to resources during the migration process. After the migration is complete, plan to re-enable SID filtering.

Practice: Planning Forest Migration to Windows Server 2008

Tailspin Toys has a fifteen-domain Active Directory forest that contains a mix of domains running at the Windows 2000 Mixed, Windows Server 2003 Interim, and Windows Server 2003 functional levels. All domains running at the Windows 2000 Mixed and Windows Server 2003 Interim functional levels contain Windows NT 4.0 DCs. You are planning the transition of the Tailspin Toys environment so that the forest operates at the Windows Server 2008 functional level.

The trafalgar.tailspintoys.internal, warragul.tailspintoys.internal, and bairnsdale.tailspintoys.internal domains are running at the Windows Server 2003 interim level. Five computers running Windows NT 4.0 are functioning as backup DCs in each of these domains.

The yarragon.tailspintoys.internal, traralgon.tailspintoys.internal, and morwell.tailspintoys.internal domains contain only Windows 2000 Server DCs. The existing DC hardware in each of these domains will support Windows Server 2008 DCs if they are running the Server Core installation. You want to deploy RODCs at several sites within these domains, and budget is available for one new Windows Server 2008 DC, including hardware, for each of these domains.

Exercise Plan the Migration of the Tailspin Toys Forest to Windows Server 2008

In this exercise, you will review the aforementioned business and technical requirements as part of planning a migration to Windows Server 2008 AD DS at Tailspin Toys.

1.Which steps should you include in your plans with respect to the tailspintoys.internal root domain?
  • Join a Windows Server 2008 member server to the domain.

  • Run adprep /forestprep on the schema master.

  • Run adprep /rodcprep on the schema master.

This is because you must deploy RODCs in several domains in the forest.

2.Which steps should you include in your plans to transition the yarragon.tailspintoys.internal domain to the Windows Server 2008 functional level?
  • Ensure that all Windows 2000 Server DCs have SP4 hotfix 265089 applied.

  • Ensure that adprep /rodcprep has been run on the schema master.

  • Join the Windows Server 2008 member server to the domain.

  • Run adprep /domainprep /gpprep on the infrastructure master in the domain.

  • Promote the Windows Server 2008 member server to DC. Seize all domain FSMO roles for this DC.

  • Demote existing Windows 2000 Server DCs.

  • Upgrade the domain functional level to Windows Server 2008.

  • Perform clean installations of Windows Server 2008 Server Core on the hardware originally used by the Windows 2000 DCs.

  • Promote these computers running Windows Server 2008 Server Core to DCs or RODCs as necessary.

3.What steps must you perform in the trafalgar.tailspintoys.internal, warragul.tailspintoys.internal, and bairnsdale.tailspintoys.internal domains before you can make any modifications to the tailspintoys.internal forest?
  • You must decommission Windows NT 4 DCs.

  • You must upgrade the domain functional level to Windows Server 2003. (Although Windows 2000 Native would work, these domains were originally at the Windows Server 2003 interim functional level.)

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