Microsoft® Windows® Server 2008 R2 White Paper Upgrading from Windows 2000 to Windows Server 2008 R2

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Microsoft® Windows® Server 2008 R2 White Paper

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Upgrading from Windows 2000 to Windows Server 2008 R2

Microsoft Corporation

Published: December 2009


The Microsoft® Windows® Server 2008 R2 provides significant enhancements over the Windows 2000 family of server products. This document provides an overview of the reasons to move to more recent versions of the operating system as well as information on the migration process, including references to various tools and resources.

© 2009 Microsoft Corporation. All rights reserved. The information contained in this document represents the current view of Microsoft Corporation on the issues discussed as of December, 2009. Because Microsoft must respond to changing market conditions, it should not be interpreted to be a commitment on the part of Microsoft and Microsoft cannot guarantee the accuracy of any information presented after the date of publication.
Microsoft, Active Directory, BitLocker, Hyper-V, MSDN, Silverlight, Visual Studio, Windows, the Windows logo, Windows PowerShell, Windows Vista, and Windows Server are either registered trademarks or trademarks of Microsoft Corporation in the United States and/or other countries.
All other trademarks are property of their respective owners.


Introduction 3

Introduction 3

Why Migrate to Newer Technology? 5

Why Migrate to Newer Technology? 5

A variety of benefits… 5

Choosing the Best Edition of Windows Server 6

Choosing the Best Edition of Windows Server 6

Selecting an Equivalent Edition 6

Reference Points 6

Active Directory Considerations 7

Active Directory Considerations 7

Domain Controllers 7

Raising Domain Functional Levels 8

Raising Forest Functional Levels 8

Application Compatibility 9

Application Compatibility 9

The benefits of upgrading applications running on Windows Server 2000 to Windows Server 2008 R2 9

Upgrading applications from Windows Server 2000 to Windows Server 2008 R2 9

Migrating 3rd party packaged ISV applications 9

Migrating custom applications 9

Resources 10

IT-Professional Resources 10

ISV/Developer Resources 11

Planning a Migration 12

Planning a Migration 12

Next Steps 12

Microsoft Assessment and Planning Toolkit (MAP) 12

Resources 12

Microsoft Deployment Toolkit (MDT) 12

Resources 13

Specific Workloads 16

Specific Workloads 16

Databases 16

Top 10 Reasons to Upgrade 16

Resources 17

Web Servers 17

Resources 18

Active Directory 18

Resources 18

Print Servers 19

Resources 19

File Servers 19

Resources 19

Failover Clustering 19

Resources 19

Terminal Servers (Remote Desktop Services) 19

Resources 19

General Information 20

Resources 20

Summary 21

Summary 21

Related Links 22

Related Links 22


Microsoft’s Support Lifecycle policy was originally announced on October 15, 2002 and the policy update went into effect June 1, 2004. The Support Lifecycle policy provides for at least 5 years of mainstream support followed by 5 years of extended support.

After 10 years of support, Windows 2000 Server will finally end support on July 13, 2010. As part of this retirement, updates – including security updates – will no longer available. While individual custom support agreements would enable customers to continue running in a supported environment after this date, most IT professionals would agree that the time has come to plan a migration to newer versions of Windows Server. In addition, Windows Server 2003 will be entering extended support at the same time as Windows 2000 end of life. More details on Microsoft’s Lifecycle policy can be found at

Newer Microsoft® Windows® Server operating systems like Windows Server 2008 and R2 represent a significant advancement over the Microsoft Windows 2000 and 2003 families of operating systems. Each edition builds on the strengths of previous versions and leverages new innovations in technology to provide a platform that is more productive, dependable, and connected than ever before. New and improved file, print, application, Web, and communication services provide a more robust, comprehensive platform for your mission-critical business resources. Integrated features such as the Active Directory® service and enterprise-class security services allow you to provide secure yet flexible access to all the resources your users need. And new capabilities such as Microsoft’s server virtualization technology Hyper-V provide virtualization opportunities previously unavailable, and at no additional cost.

This document provides an overview of the migration process and provides information on some of the basic decisions you will make during the process. This document also provides pointers to the set of documents that provide more detailed instructions on moving from Windows 2000 to newer versions of Windows Server.

There have been hundreds, if not thousands, of improvements to Windows Server since the release in 2000. A complete and detailed comparison of newer versions of Windows Server to Windows 2000 Server is beyond the scope of this paper, but some of the advantages include:

Active Directory. The Active Directory service includes improved methods for finding and changing the location or attributes of objects, command-line tools, greater flexibility in working with the schema, application directory partitions and easier management. As directory-enabled applications become more prevalent, organizations can utilize the capabilities of Active Directory to manage even the most complicated enterprise network environments.

Application Server. Advances in Windows Server provide many benefits for developing applications, including simplified integration and interoperability, and increased efficiency, all of which results in lower total cost of ownership (TCO) and better performance.

Failover Clustering. Installation and setup is much easier and more robust and enhanced network features provide greater failover capabilities and higher system uptime. Clustering services have become increasingly essential for organizations deploying business-critical e-commerce and line-of-business applications.

Backup. Windows Server helps ensure higher reliability with features such as Automated System Recovery (ASR), making it easier to recover your system, back up your files, and maintain maximum availability. A faster, more scalable file system infrastructure makes it easier to utilize, secure, and store files and other essential resources. The Volume Shadow Copy Service (VSS) provides an infrastructure for creating a point-in-time copy of a single volume or multiple volumes.

Internet Information Services (IIS). Microsoft has completely revised the IIS architecture in Windows Server to address the demands of enterprise customers, Internet service providers (ISPs), and hosters.

Management Services. Easier to deploy, configure, and use, Windows Server provides powerful new remote management capabilities and Windows PowerShell which is both a command line environment and a scripting language which enables the automation of many management tasks.

Networking and Communications. Networking improvements and new features in Windows Server extend the versatility, manageability, and dependability of network infrastructures, expanding on the foundation established in Windows 2000 Server.

Security. Windows Server provides additional – and improved – security features, making it easier to secure a full range of devices. New security features include the Encrypting File System (EFS), certificate services, and Data Execution Prevention (DEP). The server core installation option can also help reduce attack surface and the need for updates.

Storage Management. Newer versions of Windows Server introduce new and enhanced features for storage management, making it easier and more reliable to manage and maintain disks and volumes, backup and restore data, and connect to Storage Area Networks (SANs).

Terminal Server – now Remote Desktop Services. Windows Server now offers new options for remote desktops, and enhances the value of legacy and “thin client” devices. Remote Desktop Services helps simplify remote connectivity, enabling rich applications to be accessed from a web page and seamlessly integrated with a local desktop, improving remote worker efficiency.

Windows Media Services. Windows Media® Services is the server component of Windows Media Technologies used to distribute digital media content over corporate intranets and the Internet. In addition to traditional digital distribution services, such as File and Web services, Windows Media Services delivers the most reliable, scalable, manageable, and economical solutions for distributing streaming audio and video.

Several areas entirely new to more modern versions of Windows Server include:

Virtualization. Whether consolidating underutilized servers through server virtualization or virtualizating the delivery of an individual application to desktop clients, the latest versions of Windows Server offer cost-effective virtualization capabilities unimagined in the Windows 2000 Server era.

Improved Power Efficiency. Over the past 10 years datacenters have grown, power costs have climbed, and environmental concerns have emerged as a significant influence on business choices – and the bottom line. Windows Server 2008 R2 is up to 18% more power efficient than prior editions of Windows Server.

Better Together with Windows 7. Windows Server 2008 R2 and Windows 7 were developed in conjunction with one another, providing the opportunity to introduce features such as DirectAccess and BranchCache. DirectAccess allows users to connect to corporate resources without the need for a VPM – if you’re on the Internet you’re on the corporate network – securely. Administrators can manage remote systems connected through DirectAccess as well. BranchCache helps reduce WAN bandwidth usage in branch offices by enabling the automatic caching of files needed by multiple users – speeding users access to files and helping improve their network experience and productivity.

Why Migrate to Newer Technology?

A variety of benefits…

Migrating to a newer version of Windows Server – particularly the just-released Windows Server 2008 R2, and modern server hardware, offers a variety of advantages.

Security. Newer versions of Windows Server are more secure, and currently-supported versions of Windows Server receive updates on an ongoing basis.

Compliance. Currently supported software, such as newer versions of Windows Server, can help businesses comply with various government regulations and standards that apply to many businesses.

Cost. Modern server hardware and operating systems are more stable, helping avoid costly downtime, and power-efficent, helping to save electricity. Up-to-date hardware and software, still supported by vendors, represent a more cost-effective method to deliver business solutions.

Performance. Newer, more powerful hardware and more recent versions of Windows Server perform better, offer new capabilities (faster network connections, virtualization capabilities…) and are more power efficient than older versions.

New Capabilities. Newer versions of Windows Server offer new capabilities which can help improve productivity of IT staff and other workers. For example DirectAccess, new to Windows Server 2008 R2, enables users to stay connected to corporate resources wherever they are on the internet, while administrators can manage those users laptops as if they were in the office. Hyper-V, Microsoft’s hypervisor technology for server virtualization, enables businesses to consolidate frequently underutilized server hardware, helping create a more flexible, efficient, and cost effective server environment.

Windows Server 2008 R2 has been well received by partners, and customers. Customer case studies showcasing the benefits and cost savings of newer versions of Windows Server are available at

The press has recognized the benefits of Windows Server 2008 R2, as exemplified here:

“With all these new features, R2 is certainly the best Windows Server operating system to date.” Jonathan Hassell, ComputerWorld

“This is, in short, Microsoft's best server operating system to date.” Samara Lyn, CRN

“This version of Windows Server is also the first in a decade to be released in tandem with a new Windows client (in this case, Windows 7). As such, Windows Server 2008 R2 includes many features that make it and Windows 7 "better together.“ Jason Perlow, ZDNet

Furthermore, Forrester Consulting conducted a study on Windows Server 2008 R2 using their Total Economic Impact (TEI) Model. They interviewed real customers who have already deployed R2, and the model is based on their actual results. Their framework identified 13 potential areas of savings for customers, and can be used as a template for examining potential savings in your environment. The TEI model shows that medium sized customers could see a break-even Return on Investment (ROI) in less than 6 months. The study is available at

Choosing the Best Edition of Windows Server

Selecting an Equivalent Edition

A first step in choosing the best operating system is determining the nearest equivalent to what you are now running. The Web Edition is a completely new edition, and so it doesn’t have an equivalent in the Windows 2000 family of operating systems. The other Windows Server 2008 R2 operating systems map directly to existing Windows 2000 operating systems, as shown in Table 1.

Windows 2000 Server Family

Windows Server 2008 R2 Family

Windows 2000 Server

Windows Server 2008 R2 Standard

Windows 2000 Advanced Server

Windows Server 2008 R2 Enterprise

Windows 2000 Datacenter Server

Windows Server 2008 R2 Datacenter

No Equivalent

Windows Server 2008 R2 Web

Table 1 Migrating to an Equivalent Edition

Windows 2000 Server hardware may not be able to support Windows 2008. Assuming a particular server does meet the requirements for 2008, upgrading Windows 2000 to 2008 or R2 is a two step process: Upgrading from Windows 2000 Server to Windows 2003 SP2 and then to Windows 2008. Given the scope of changes between Windows 2000 Server and Windows Server 2008 such an upgrade process is not recommended. (Because Windows Server 2008 R2 is 64-bit only, it is not possible to upgrade from Windows 2000 Server to Windows Server 2008 R2 – even “through” Windows Server 2003.)

In terms of migrating a workload from an older server to a newer server running Windows Server 2008 or R2, in some cases it may be possible to migrate, easing the transition by preserving settings and configuration. Because server roles were introduced after Windows 2000 Server – and given the scope of changes and enhancements to server capabilities over the past 10 years – such a migration path would also, in many cases, involve moving first to Windows Server 2003 and then to Windows Server 2008 or R2.

Given the complications – whether upgrading or migrating – of attempting to move “through” Windows Server 2003 on the way to 2008 or R2 in these scenarios, they are not recommended. A clean install of Windows Server 2008 or R2 – typically on new server hardware is generally recommended.

Reference Points

For a comprehensive list of hardware and software supported by the Windows Server operating system, see the Windows Server Catalog at

Active Directory Considerations

The Active Directory service is an essential and inseparable part of the Windows Server network architecture that provides a directory service designed for distributed networking environments.

Because of this central role – and the complexities involved in selecting a Domain Functional Model – and updating that model at the right point in the migration process from Windows 2000 Server to newer versions of Windows Server, this paper will consider Active Directory at some length.

Active Directory provides a single point of management for Windows-based user accounts, clients, servers, and applications. It also helps organizations integrate systems not using Windows with Windows-based applications and Windows-compatible devices, thus consolidating directories and easing management of the entire network operating system. Companies can also use Active Directory to extend systems securely to the Internet. Active Directory thus increases the value of an organization's existing network investments and lowers the overall costs of computing by making the Windows network operating system more manageable, secure, and interoperable.

Active Directory plays such an important role in managing the network, that as you prepare to move to a newer version of Windows Server, it is helpful to review the new features of the Active Directory service.

Domain Controllers

The upgrade to Active Directory can be gradual and performed without interrupting operations. If you follow domain upgrade recommendations, it should never be necessary to take a domain offline to upgrade domain controllers, member servers, or workstations.

In Active Directory, a domain is a collection of computer, user, and group objects defined by the administrator. These objects share a common directory database, security policies, and security relationships with other domains. A forest is a collection of one or more Active Directory domains that share the same class and attribute definitions (schema), site and replication information (configuration), and forest-wide search capabilities (global catalog). Domains in the same forest are linked with two-way, transitive trust relationships.

To prepare for upgrades in a domain containing Windows 2000 domain controllers, it is recommended that you apply Service Pack 2 or later to all domain controllers running Windows 2000.

Before upgrading a domain controller running Windows 2000 to Windows Server 2003, or installing Active Directory on the first domain controller running Windows Server 2003, ensure that your server, your forest, and your domain are ready.

Two command-line tools are helpful in upgrading domain controllers:

Winnt32. Use Winnt32 to check the upgrade compatibility of the server.

Adprep. Use Adprep on the schema operations master to prepare the forest. Running Adprep on the schema master updates the schema, which in turn replicates to all of the other domain controllers in the forest.

Note that until you have used Adprep to prepare the forest and the domains within the forest, you cannot upgrade domain controllers running Windows 2000 to Windows Server 2003, or add domain controllers running Windows Server 2003 to Windows 2000 domains.

With the new Active Directory features in Standard, Enterprise, and Datacenter editions, more efficient administration of Active Directory is available to you.

Some new features are available on any domain controller running a newer version of Windows Server, while others are only available when all domain controllers of a domain or forest are running newer versions of Windows Server.

Raising Domain Functional Levels

Domains can operate at various functional levels: Windows 2000 mixed, Windows 2000 native, and Windows Server 2003 (which only includes domain controllers running Windows Server 2003), Windows Server 2008, and Windows Server 2008 R2.

Once all domain controllers are running a newer version of Windows Server, you can raise the Domain and Forest Functionality to Windows Server by opening Active Directory Domains and Trusts, right clicking the domain for which you want to raise functionality, and then clicking Raise Domain Functional Level.

Note that once you raise the domain functional level, domain controllers running earlier operating systems cannot be introduced into the domain. For example, if you raise the domain functional level to Windows Server 2003, domain controllers running Windows 2000 Server cannot be added to that domain. However such servers can be members of the domain.

Raising Forest Functional Levels

Forest functionality enables features across all the domains within your forest.

The following table describes the forest-wide features that are enabled for the corresponding forest functional level:

Forest Feature

Windows 2000

Windows Server 2003 & 2008

Global catalog replication tuning



Defunct schema objects



Forest trust



Linked value replication



Domain rename



Improved replication algorithms



Dynamic auxiliary classes



InetOrgPerson objectClass change



Table 3 Forest-wide Features Enabled for Corresponding Forest Functional Level

Application Compatibility

The deployment of an operating system in any organization is a very large project. Application compatibility with the new operating system is one of the most critical steps in the testing and planning phases of a successful deployment. This entails verifying that all existing software and any planned software will function correctly on the new operating system at least as well as it did on the old operating system.

The benefits of upgrading applications running on Windows Server 2000 to Windows Server 2008 R2

Windows Server 2008 R2 includes all of the features of an enterprise class application server. Windows Server 2008 R2 application and web platform enhancements provide many benefits for developing applications including:

  • Simplified IT management, integration and interoperability.

  • Consolidation and virtualization.

  • Increased efficiency and productivity.

  • Scalability and better performance.

  • Reduced costs and risks.

Upgrading applications from Windows Server 2000 to Windows Server 2008 R2

As you prepare to move your applications to a newer version of Windows Server, it is important to remember key steps of this process to ensure a smooth transition and minimize customers’ impact.
  • Migrating 3rd party packaged ISV applications

  1. Make an inventory of, and prioritize, applications

  2. Identify applications that might have a compatibility issue by verifying whether the ISV who created the application supports or has logoed the application(s) on a newer version of the operating system. (The Windows Server Catalog contains a list of all ISVs that have pledged to support their apps on Windows Server 2008 R2 as well as a list of all logoed applications)

  3. If an application is not supported or logoed on Windows Server 2008 R2, contact the ISV to obtain a new version of the application that runs on the new operating system or request support for your obsolete application.

  4. If the ISV does not support their application on newer versions of Windows Server, or if you are unable to determine the ISV’s policy, you may still assess your application's compatibility, security, stability, reliability and availability in a Windows Server 2008 R2 environment by taking advantage of Microsoft’s free self-test tools and resources listed below.

  5. Prepare for an application upgrade by reviewing the links and resources listed below. Ease the process by identifying and eliminating problems before upgrading.

  6. Upgrade and deploy with confidence.
  • Migrating custom applications

  1. Make an inventory of, and prioritize, applications.

  2. Download the free test tools and resources to assess your application’s compatibility on newer versions of Windows Server.

  3. Create a test plan for all applications that need to run on the upgraded servers.

  4. Empower your build/test teams with more comprehensive test scenarios based on Microsoft’s application development/testing standards and recommended upgrade practices. Test tools such as the Application Compatibility Toolkit (ACT Version 5.5) and Software Certification Toolkit may also be used as black-box evaluators to identify any potential compatibility issues.

  5. Create a remediation plan if needed to update your applications. Learn about Windows Server 2008 R2 application and web platform enhancements such as:

    • Build More Flexible Web Applications: Internet Information Server 7.5, PHP optimized, ASP .NET on Server Core, Enhanced FTP and WebDAV

    • Build Connected Systems: Windows Communication/Workflow Foundation, Windows Process Activation Service, Microsoft Message Queue

    • Build Scalable Applications: Support for up to 256 logical processors, NUMA support, Thread Pool, Thread Ordering Service

    • Leverage Virtualization: Hyper-V with Live Migration

    • Extend File System: File Class. Infra.

    • Design Highly Manageable Applications: Microsoft Management Console, Windows PowerShell™ 2.0, Windows Task Scheduler, Windows Eventing, Windows Installer, ClickOnce

    • Develop Federation-Aware Applications: Active Directory Federation Services, Active Directory Lightweight Directory Services, Windows Authorization Manager

    • Develop more reliable applications: Application Recovery and Restart, Restart Manager, Transactional NTFS, Transactional Registry

  6. Prepare for an application upgrade by reviewing the links and resources listed below.

  7. Upgrade and deploy with confidence.


Microsoft offers a variety of free tools and resources to help IT professionals, ISVs and custom application developers to not only prepare and get ready for an application upgrade, but also to quickly and efficiently test any application for compatibility with Windows Server 2008 R2.

IT-Professional Resources

Application Compatibility Resources for IT Professionals and Developers
Customer/IT Pro guide to Windows Server application compatibility. Free resources and tools for quick compatibility self-test of apps running on Windows Server 2008 R2.

Getting Started with Application Compatibility in a Windows Deployment
After reading this document, you should have a clear idea of where to start in the process of evaluating the impact of application compatibility in your deployment project (Windows 7).

Application Compatibility Tech Center on TechNet
Get tools and resources to reduce the time, cost, and complexity of addressing application compatibility (Windows 7).

Application Considerations When Upgrading to Windows Server 2008
This document contains the information that you need if you have line-of-business (LOB) or non-Microsoft applications and you are upgrading to the Windows Server 2008 operating system.

Windows Server 2008 R2 Supported Applications
This page shows the support policy for running Microsoft server software, desktop applications and technologies running on Windows Server 2008 R2.

Windows Server Catalog
Identify and verify status of tested hardware and software products for Windows Server. Find a list of supported applications on Windows Server 2008 R2 for which the applicable ISV has pledged to offer frontline technical support on the latest Windows Server platform today or at a future date.

ISV/Developer Resources

Windows 7 and Windows Server 2008 R2 Application Quality Cookbook
Windows 7 and Windows Server 2008 R2 Application Quality Cookbook: A Developer's Guide to Application Compatibility, Reliability, and Performance.

ISV Application Readiness and Certification
Describes how to get your applications ready for Windows Server 2008 R2.

Microsoft Application Compatibility Toolkit (ACT) Version 5.5
The Application Compatibility Toolkit (ACT) enables software developers, independent software vendors (ISVs), and IT professionals who work in a corporate environment to determine, before rolling out within the organization, whether their applications are compatible with a new version of the Windows operating system.

The Application Compatibility Toolkit (ACT) contains several tools that will help make this process easier to manage. The ACT provides tools to test applications both during the development phase and during deployments. It also provides tools that will enable you to gather data about the applications installed on every Windows computer in the network and to package the necessary compatibility fixes for each of those computers

Windows Developer Center on MSDN
Get help, guidance, and tools to help you identify and work through compatibility issues you might encounter when migrating your applications to Windows 7.

MSDN Windows Server 2008 R2 Developer Resources

Set of great developer resources focused on key technology investment areas of Windows Server 2008 R2.

MSDN Windows Server 2008 Application Compatibility and Certification Support Forum
Forum for developers to discuss Windows Server 2008 software certification and application compatibility.

Windows Server Certification and Application Compatibility Blog

Software certification and application compatibility testing tools guides.

Planning a Migration

With the end of support in sight, now is the time to begin planning a move from Windows 2000 Server to a newer version of Windows Server. This section of the paper will help provide a basic outline to help with planning a migration, and includes a variety of resources to help execute the migration.

Next Steps

At the end of this document are a variety of resources that can help with your migration. Next steps you should consider include:

  • Run the Microsoft Assessment and Planning Tool (MAP) in order to identify Windows 2000 Servers in your environment

  • If you have applications you’re concerned about, explore our Application Compatibility Toolkit

  • Depending on the specific workload you’re migrating, consult one of the more detailed documents listed at the end of this document

Windows Server 2008 R2 cannot be upgraded directly over Windows 2000 Server. However, a variety of documentation and tools are available to help migrate key workloads.

Microsoft Assessment and Planning Toolkit (MAP)

The Microsoft® Assessment and Planning (MAP) Toolkit helps you understand your current IT infrastructure and determine the right Microsoft technologies for your IT needs. It is a powerful inventory, assessment, and reporting tool that can securely inventory small or large IT environments without requiring the installation of any agent software in your environment. The data and analysis that this tool provides can significantly simplify the planning process for a wide range of migration projects.

The Microsoft Assessment and Planning (MAP) Toolkit is an agentless toolkit that finds computers on a network and performs a detailed inventory of the computers using Windows Management Instrumentation (WMI) and the Remote Registry Service. The data and analysis provided by this toolkit can significantly simplify the planning process for migrating to newer versions of Windows Server. Assessments for Windows Server 2008 R2, Windows Server 2008, Windows 7, and Windows Vista include device driver availability as well as recommendations for hardware upgrades.

Once the toolkit has identified the Windows 2000 Servers in the environment, individual plans can be made for each server. With the information provided by the MAP tool, administrators can begin to plan research and test on various hardware, drivers, and software in the Windows 2000 Servers to be migrated.


  • Microsoft Assessment and Planning (MAP) Toolkit

Microsoft Deployment Toolkit (MDT)

The Microsoft Deployment Toolkit 2010 provides a common console with the comprehensive tools and guidance needed to efficiently manage deployment of Windows 7 and Windows Server 2008 R2. Microsoft Deployment Toolkit 2010 is the recommended process and toolset to automate desktop and server deployment. Microsoft Deployment Toolkit 2010 provides detailed guidance and job aids for every organizational role involved with large-scale deployment projects


  • Microsoft Deployment ToolkitA support site for Windows 2000 Server migrations

  • Microsoft Deployment ToolkitMDT 2010

  • Guides to Migrate Server Roles to Windows Server 2008 R2 on TechNet

  • Step By Step guides to support the new file services migration toolkit

Windows 2000 Server Role

Windows Server 2003 SP2

Windows Server 2008

Windows Server 2008 R2


Directory Services






Domain Controller




The upgrade process for a Windows 2000 Domain Controller consists of installing a new Windows Server 2008 R2 server and then promoting it to a domain controller in the domain.

AD Certificate Services




You only need to upgrade the operating system to upgrade the Certificate Authority or any other AD Certificate Services component. You can also migrate by backing up and restoring the Certificate Authority.










For a Windows 2000 Server to Windows Server 2008 scenario, the recommended approach is to remove FRS and then set up DFSR replication.

Cluster Service




There is no direct path for migrating to Windows Server 2008. Changes in Server 2008 requirements for shared storage will prevent using the original storage in a 2008 Failover Cluster Server.
It would be possible to perform a rolling upgrade through Windows Server 2003. Once the cluster is running as a Windows 2003 Server Cluster, the Failover Cluster Migration Wizard in 2008/2008R2 can be used.





Windows Deployment Services is included in Windows Server 2003 SP2. If you already had RIS installed and configured, when you install Windows server 2003 SP2, Windows Deployment Services will automatically be installed, however, it must be configured.

Print Server




The Print Migration Wizard in Windows Server 2008 can provide needed migration from Windows 2000 Server. Due to the new Print Isolation architecture in Windows Server 2008 R2, the print migration wizard/printbrm.exe will not migrate print drivers to Windows Server 2008 R2.

Terminal Services




There is no migration per se, an upgrade or clean install of the newer operation system is required. There is no direct in-place upgrade path available for Windows 2000 Server to Windows Server 2008 or Windows Server 2008 R2.

Terminal Server Licensing





Networking Server Roles



















To migrate IAS from Windows 2000 Server to Windows Server 2008 or 2008 R2, the recommended process is to use a Windows Server 2003 system as an intermediary. Or proceed with a clean install.

NLB Cluster




It is possible to upgrade a Network Load Balancing cluster by taking the entire cluster offline and upgrading all the hosts individually. It would also be possible to leave the cluster on line and perform a rolling upgrade





There is no direct migration from RRAS in Windows 2000 Server to Routing and Remote Access in newer operating systems. Settings should be documented and manually configured on the new server.





Migration would be possible by installing the Microsoft® Windows® Server 2003 operating system and new version of IIS on a new server and then moving, or reinstalling, existing Web sites and applications to that server.

Specific Workloads

The sections below contain additional information regarding the benefits of migrating specific workloads, and resources and tools to help.


Just as Windows Server has evolved since 2000, so has SQL Server.

With the release of the most recent version of SQL Server, Microsoft has delivered a Trusted, Productive and Intelligent Enterprise Data Platform. There are enhancements and new capabilities engineered into SQL Server 2008 to enable your applications to run better and reduce the amount of time you need to spend managing them. If you have been running existing applications on SQL Server 2000 or 2005, you will find a set of exciting new capabilities to improve your applications and reduce support needs within a familiar management interface. Many of these new features can provide immediate benefits without the need to make application changes.

Top 10 Reasons to Upgrade

1. Experience the benefits right away - Significant enhancements ranging from Data and Backup compression to query performance and enhanced database mirroring are available without the need to modify your existing applications.

2. Enhanced security and auditing – Get data encryption and database auditing capabilities within existing applications.

3. Improved system management capabilities - Features like policy based server management and new tools such as Performance Data Collection help you effectively manage the growth of your data.

4. Performance Enhancements – There have been many performance enhancements made throughout the technology stack, including enhancements within Analysis Services, Reporting Services and Integration Services. For example Unisys and Microsoft set a new ETL performance record by loading one terabyte of data in less than 30 minutes using SQL Server 2008 Integration Services. Read about additional performance records.

5. Predictable System Response – New Features such as query governor and data compression along with general scalability enhancements provide scalable solutions that are more reliable for very large enterprise systems.

6. Developer productivity - Tools like Entity Framework and LINQ, and new date/time, FILESTREAM and spatial datatypes provide powerful and easy to use application development enhancements.

7. Enhanced Business Intelligence capabilities – additional reporting capabilities integrated with Microsoft Office applications and a new report designer application allows the creation of enterprise reports without the need for Developer Studio.

8. Application Compatibility & ease of Migration - There are upgrade tools available from Microsoft to help manage your upgrade from prior versions. Compatibility has been maintained with the majority of functionality which should enable most applications to upgrade seamlessly. Learn more about all the system changes from the prior version.

9. Mainstream support – With the latest version of SQL Server you can benefit from a long term and current support path. As of April 2008 SQL Server 2000 has moved off Mainstream support to an extended support path.

10. Consistent pricing and support – Microsoft continues its pricing policies of SQL Server 2005 with some additional improvements. In addition, by participating in Microsoft’s Software Assurance program you are eligible for product upgrades, support and other benefits.


Additional technical details on planning and how-to guides for your upgrade are available at these links:

  • Version and Edition Upgrades

  • Using Upgrade Advisor to Prepare for Upgrades – The upgrade advisor allows you to identify syntax and other incompatibility issues that need to be addressed before you can move an older SQL Server database over to SQL Server 2008.

  • SQL Server Upgrade Assistant - The SQL Server Upgrade Assistant helps you capture a baseline on your earlier version of SQL Server and compare the same workload on SQL Server 2008. It allow you to compare key performance characteristics so you know exactly what to expect after the upgrade. Note that it is different from Upgrade Advisor and is usually used in conjunction with it

  • Migrating to SQL Server 2008

  • Upgrading to SQL Server 2008

  • SQL Server 2008 Upgrade Technical Reference Guide

  • SQL Server 2008 Upgrade How-to Topics

  • Getting Assistance with SQL Server 2008

  • Check Parameters for the System Configuration Checker

Web Servers

Windows Server 2008 R2 includes many enhancements that make this release the most robust Windows Server Web application platform yet. It offers an updated Web server role, Internet Information Services (IIS) 7.5, and greater support for .NET on Server Core. Design goals for IIS 7.5 concentrated on improvements that enable Web administrators to more easily deploy and manage Web applications, and that increase both reliability and scalability. Additionally, IIS 7.5 has streamlined management capabilities and provides more ways than ever to customize your Web serving environment.

The following improvements to IIS and the Windows Web platform are included in Windows Server 2008 R2:

  • Reduced Effort to Administer and Support Web-Based Applications

  • Reduced Support and Troubleshooting Effort

  • Improved File-Transfer Services

  • Ability to Extend Functionality and Features

  • Improved .NET Support

  • Improved Application Pool Security


  • IIS 6.0 Deployment Guide - This guide provides prescriptive, task-based, and scenario-based guidance to help you design an IIS 6.0 solution that meets the specific needs of your organization.

  • How to Migrate from IIS 6.0 to IIS 7.0 - This quick guide will help you migrate a Web site from IIS 6.0 to IIS 7.0 using the Web Deployment Tool.

Active Directory

By upgrading your network operating system, you can maintain your current network and domain configuration while improving the security, scalability, and manageability of your network infrastructure.

Before you upgrade your Windows 2000 or Windows Server 2003 Active Directory domains, review your business objectives and decide how they relate to your existing Active Directory infrastructure. Although your objectives might not require other significant changes to your existing environment, the operating system upgrade is an opportune time to review your existing Active Directory design, including your Active Directory logical structure, site topology, and domain controller capacity. You might find opportunities for increased efficiencies and cost savings that you can incorporate into your upgrade process. In addition, ensure that you test your upgrade process in a lab and pilot program.

When the domain upgrade process is complete, all domain controllers will be running Windows Server 2008 or Windows Server 2008 R2, and the Active Directory Domain Services (AD DS) domains and forest will be operating at the Windows Server 2008 or Windows Server 2008 R2 functional level. At the Windows Server 2008 R2 forest functional level, you can take advantage of all the advanced AD DS features.


  • How to upgrade Windows 2000 domain controllers to Windows Server 2003:

  • Upgrading Active Directory Domains to Windows Server 2008 AD DS Domains - This guide provides detailed guidance for upgrading Windows 2000 or Windows Server 2003 Active Directory domains to Windows Server 2008 Active Directory Domain Services (AD DS) domains.

  • Active Directory Domain Services and DNS Server Migration Guide - This document provides guidance for migrating the Active Directory Domain Services (AD DS) Server or Domain Name System (DNS) Server roles from an x86-based or x64-based server running Windows Server 2003, Windows Server 2008, or Windows Server 2008 R2 to a new Windows Server 2008 R2 server.

  • Local User and Group Migration Guide - Administrators can use Windows Server Migration Tools to migrate server roles, features, shares, operating system settings, and other data to computers that are running Windows Server 2008 R2.

  • Performing the Upgrade of Active Directory Domains to Windows Server 2008 AD DS Domains:

  • The same information is also available as a document here:

  • Verifications that can be made and hotfixes that can be installed before beginning a migration:

  • Active Directory Migration Tool 3.1

  • ADMT v3.1 Guide: Migrating and Restructuring Active Directory Domains

Print Servers


  • Migrate Print Servers – See the Migrate Print Servers section of the Print Management Step-by-Step Guide for detailed information about migrating Print Servers.

  • Migrating and Consolidating Print Servers – This paper presents the system administrator with several methods for performing print server consolidations, offering a range of automation and flexibility.

File Servers


  • Microsoft File Server Migration Toolkit 1.2:

  • File Services Migration Guide:

Failover Clustering


  • How to Upgrade a Cluster from Windows 2000 to Windows Server 2003 – This document describes how to upgrade a cluster from Windows 2000 to Windows Server 2003

  • How to perform a rolling upgrade from Windows 2000 to Windows Server 2003 – This document describes how to perform a rolling upgrade from Windows 2000.

  • Additional information on rolling upgrades:

  • Documentation discussing special cases and consideration when migration to a R2 cluster (from 2003, 2008 or R2). Additional considerations needed for DFS-Replication, DHCP, (MS)DTC, Exchange, File Server, MSMQ, Print, SQL, VMs and 3rd Party Resources.

  • General Windows Server Failover Clustering migration guide:

  • More detailed guidance on DHCP:

Terminal Servers (Remote Desktop Services)


  • Upgrading to Windows Server 2003 Terminal Server - This document describes how to upgrade to Windows Server 2003 Terminal Server

General Information

The following resources provide additional general information


  • How to Migrate Server Roles to Windows Server 2008 R2 – This document describes how to migrate server roles to Windows Server 2008 R2



  • Migration from 2003 to 2008: Windows Server Migration Tools

  • Why Upgrade: Upgrading from Windows 2000 Server to Windows 2008 Server R2

  • Guide to Upgrading to Windows 2008

  • Infrastructure Planning and Design Guidelines:


The Windows Server 2003 and Windows Server 2008 provide significant enhancements over the Windows 2000 family of server products.

Active Directory becomes an even more powerful administrative resource and can be deployed in heterogeneous environments including Windows 2000 Servers. The Active Directory Installation Wizard simplifies deployments.

The Microsoft Assessment and Planning toolkit can help locate servers running Windows 2000 Server and provide detailed configuration information, simplifying planning migrations. While the Application Compatibility Toolkit eases the process of verifying whether existing applications will continue to work with the new operating system.

Considering the age of Windows 2000 Servers, now is the time for all organizations – large and small – to plan a migration and begin enjoying the benefits of newer versions of Windows Server.

Related Links

See the following resources for further information:

Using the Application Compatibility Toolkit at

Top 10 Features for Organizations Upgrading from Windows 2000 Server at

Top 10 Features for Organizations Upgrading from Windows 2000 Server at

For the latest information about Windows Server see .

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