Upgrading Active Directory 2003 to 2008

Before driving into a blog about the upgrade process, i feel we should cover the key concepts. If you know these, scroll to the next horizontal line.

Active Directory Upgrade to 2008R2

Date: 2008-09-07

Active Directory is a fundamental part of the Microsoft Windows server operating system, plays a major role in managing and organising network resources within a Windows-NT Domain or Forest. AD Domains provide a structured, hierarchical database for which the storage and management of objects are performed. From distribution groups, group policies, member-servers (comptuers), security groups, and users; almost all of it is available at our fingertips.

Are you are of FSMO roles? If not, check back with my first blog in this series, and read the key-concepts section at the top.

I will guide you through the process of upgrading Active Directory from Windows Server 2003 to Windows Server 2008. This transition requires careful planning, proper execution, and rigorous testing to ensure a seamless migration. Let's start with Part 1, which covers the initial steps and preparations for the upgrade.

Understanding the Importance of the Upgrade

Reasons include:

improved server roles
enhanced security posture: fain-grained password policies, gpo based event logging and account auditing options)
advanced group policy management: new Preferences supporting extensible and robust administrative tasks, from mapped drives, to setting specific registry values, all with a gui based navigation
improved performance offered by Windows Server 2008: optimised for domain and database servers for enhanced end-user experience
all new PowerShell: A streamlined scripting platform, returning chaos to order with the use of command-lets (Get-ADUser ...)
better backup and recovery capabiliites: accidental object deletion, tombstone lifetimes and much more
simplified virtualisation directly on supported hardware: heard of Hyper-V yet? Its like VMware ESX, only all windows.... kinda.

1 Assess your current domain

Follow my little blue checklist on the left, and create your own checklist on the right.
This proved to be massively helpful for me; as I did this for two companies over the course of 3 months.

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2 Prepare Your Environment

Follow my little blue checklist on the left, and create your own checklist on the right.
This proved to be massively helpful for me; as I did this for two companies over the course of 3 months.

1) Run adprep32 /forestprep then adprep32 /domainprep:
This tool extends the schema to support the new features and requirements of the upgraded operating system.
Ensure that you run this tool on your existing domain controllers - mount the CD (or ISO) for Windows Server 2008R2.

Keep your eyes out for missing permissions...

Looking for a Read-Only Domain Controller? Then also run adprep32 /rodcprep.

2) Upgrade Domain Controllers: Begin the process of upgrading your existing domain controllers to Windows Server 2008 R2. I did one inline upgrade, and 2x fresh installations (VMs).
Of course we simply install new Windows Server 2008 R2 operating systems, join the domain, and then promote them to become domain controllers. How? DCPROMO

3) Raise Functional Levels: As part of the upgrade process, you can raise the domain and forest functional levels to Windows Server 2008 R2. This step unlocks advanced features and capabilities offered by the new operating system.

This process is pretty much identical to the last time i blogged about this. Checkout the last instructions here.

4) Migrate FSMO Roles: Transfer the Flexible Single Master Operations (FSMO) roles from your old domain controllers to the new Windows Server 2008 R2 domain controllers. These roles include the Schema Master, Domain Naming Master, RID Master, PDC Emulator, and Infrastructure Master.

Again this process hasn't changed. Checkout the last instructions here.

5) Test the Environment: Before fully transitioning to the new environment, perform thorough testing. This includes checking for any compatibility issues, ensuring that Active Directory replication is functioning correctly, and validating the overall health of the upgraded environment.

How exactly do we test domain controllers? Logon to things, servers, file-shares, even remote-desktop. Then read as many event log errors/warnings as you possibly can find. It'll be worth the effort.

6) Backup Everything: As a precaution, create comprehensive backups of your Active Directory and other critical data. Having a backup ensures that you can quickly recover in case of unexpected issues. Kinda goes without saying really.

7) Update Group Policies: Review and update group policies to ensure they are compatible with Windows Server 2008 R2. Be prepared to make any necessary adjustments to maintain consistency in your environment.

Don't forget to update the new Default Domain Controllers Policy, to let your backup service-account have the privilidge`logon as a batch' for every domain controller. Or it won't be able to access the NTDS database to back it up! Suppose this goes with step 6 as well :)

9) Document the whole process: Throughout this phase, keep detailed records of the steps taken and any changes made (good change management practice of course). This documentation will be invaluable for reference and troubleshooting later.

Conclusion

Upgrading Active Directory to Windows Server 2008 R2 as a crucial step towards ensureing the security, performance, and compliance of your NT Domain. This comprehensive guide has walked you through the essential steps, from assessing your environment and preparing your forest and domain to executing the upgrade seamlessly.

By following best practices and the documented procedures provided by Microsoft, you can make this transition with confidence (I did). Keep in mind that proper planning, a robust backup strategy (offers a rollback plan), and regular testing (dcdiag checks) can help you avoid unexpected hiccups during the upgrade process. Keep an eye on Microsoft Exchange or Microsoft SQL Server during this upgrade process.

Once your Active Directory is up and running on Windows Server 2008 R2, you'll be well-equipped to leverage its enhanced features, improved security, and scalability. Whether you're managing a small or large organization, this upgrade paves the way for a more efficient and secure IT environment.

If you encounter any challenges or have specific questions during the upgrade, don't hesitate to reach out to your IT team or consult Microsoft's support resources. With the right approach and careful execution, your journey to an updated Active Directory will lead to a more robust and future-ready domain.

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