This document outlines the process of upgrading from Windows Server 2003 to Windows Server 2008 R2, focusing on the importance of planning, testing, and performing backups prior to the upgrade. It covers various factors such as Active Directory enhancements, schema upgrades, and potential issues that may arise, as well as best practices for ensuring a smooth transition. The document emphasizes the need for thorough preparation and caution when demoting old domain controllers and raising domain and forest function levels.

1. Upgrading AD from
Windows Server 2003 to
Windows Server 2008 R2
Daniel Petri (dpetri@microsoft.com)
Senior Premier Field Engineer, Microsoft

2. Agenda
Why upgrade? Prepare
Action
Plan Cleanup

3. Why Upgrade your servers
In relation to Active Directory:
- RODC
- Server Core
- AD Snapshots (ntdsutil.exe, dsamain.exe)
- DS Auditing (auditpol.exe)
- Restartable AD service
- Administrative Center
- PowerShell Cmdlts
- AD Best Practice Analyzer
- Protect from accidental deletion
- GPO benefits
- Support lifecycle

4. Why Upgrade your DCs
Windows 2008 Domain Windows 2008 R2
Function Level Domain Function Level
- Authentication mechanism
- DFSR replication of Sysvol
assurance
(dfsrmig.exe)
for AD-FS
- Advanced Encryption Services (AES
- Managed Service Accounts
128 and 256) for Kerberos
(MSA)
- Last Interactive Logon Information
- Fine-Grained Password Policy Windows 2008 R2 Forest
- Personal Virtual Desktops Function Level
- Offline Domain Join (djoin.exe)
- AD Recycle Bin

5. Plan
What are the upgrade goals?
Map existing resources
What other roles do DCs perform?
Map the risks
Can you consolidate?
Can you virtualize?
Should you virtualize?
Plan for rollback

6. Identify potential issues
This is mostly because DES encryption types for the
Kerberos authentication protocol are disabled by default in
Windows Server 2008/R2.
– SAP
– Oracle Internet Directory (OID), CA Identity Manager,
Tivoli Identity Management
– Samba and other Linux/Unix interoperability
– NetApp, EMC Celera or other storage devices
– Firewalls, VPN, RADIUS
– http://support.microsoft.com/kb/977321

7. Identify potential issues
Additional considerations:
– Terminal Server License Server on a DC
– CA on a DC
– Smart Cards
– Customized password filters
– Time keeping software
– 3rd-party apps that are hard coded to work against
specific DCs
– Exchange servers with manual DC configuration

8. Test
- The bigger and more complex you are, the more you
need to test before you act.
- Consider regulations and standards (such as Change
Management procedures)
- Test environment needs to be as close to production as
possible.
- Test and production need to be totally isolated from each
other.

9. Backup
Make sure you have a recent, supported and working
backup:
- System State
- Boot Partition
- System Partition
- All GPOs (by using GPMC)
- Scripts etc.
Do NOT use a VM snapshot as backup!

10. Backup
As an extra security measure:
- Consider disconnecting one DC in addition to
backing up.
- Consider disabling outbound replication on the
Schema Master DC during the Schema upgrade.
repadmin /options <server_name>
+/-disable_outbound_repl

11. Backup
What's the tombstone lifetime (TSL)?
- Default up to Windows Server 2003 R2 = 60 days,
for later = 180 days
- If Forest is upgraded, TSL is not automatically
changed
dsquery * “cn=directory service,cn=windows
nt,cn=services,cn=configuration,dc=contoso,
dc=com” –scope base –attr tombstonelifetime

12. Permissions
Make sure the user you're working with is a
member of:
- Domain Admins
- Enterprise Admins
- Schema Admins

13. Previous Operating Systems
Make sure DFL and FFL are Windows 2000 Native
or above.
If they exist, all Windows 2000 DCs must be running
SP4.
- Issues with Win9X/NT4.0 client computers:
http://support.microsoft.com/kb/555038
http://support.microsoft.com/kb/946405
http://support.microsoft.com/kb/942564
- Issues with External Trusts to NT4.0 domains:
http://support.microsoft.com/kb/2021766

14. Domain and Forest
Check the overall health of the existing AD:
– Replication
– DNS
– Events
– Logs
Find FSMO holders:
– netdom query fsmo
Consider temporarily disabling AV on the DCs.

15. Execute – Schema upgrade
Schema upgrade is a one-way process!
- Needs to run once per forest.
- On the existing Schema Master, insert the
Windows Server 2008 R2 media, go to
x:supportadprep:
adprep.exe /forestprep
or
adprep32.exe /forestprep
- When finished, wait for replication.

16. Verify – Schema upgrade
- Check version:
dsquery * “cn=ActiveDirectoryUpdate,
cn=ForestUpdates,cn=configuration,dc=contoso,
dc=com” -scope base -attr revision
(should be 5 for 2008 R2)
dsquery * “cn=schema,cn=configuration,dc=contoso,
dc=com” -scope base -attr objectversion
(should be 47 for 2008 R2)
- Verify replication
repadmin /replsum /bysrc /bydest /sort:delta

17. Execute – Domain preparation
- Needs to run once for each to-be upgraded
domain in the forest.
- On the existing Infrastructure Master:
adprep.exe /domainprep (/gpprep)
or
adprep32.exe /domainprep (/gpprep)

18. Verify – Domain preparation
- Check version:
dsquery * “cn=ActiveDirectoryUpdate,cn=DomainUpdates,
cn=system,dc=contoso,dc=com” -scope base -attr revision
(should be 5 for 2008 R2)

19. Execute – RODC preparation
- Only needs to run once per forest, but needs to
be able to connect to all Infrastructure Masters in all
the domains in the forest.
- On any existing DC:
adprep.exe /rodcprep
or
adprep32.exe /rodcprep
http://support.microsoft.com/kb/949257

20. Verify – RODC preparation
Check version:
dsquery * “cn=ActivedirectoryRodcUpdate,
cn=ForestUpdates,cn=configuration,
dc=contoso,dc=com” -scope base -attr revision
(should be 2)

21. Demo
- Preparing the forest and domain for the first Windows
Server 2008 R2 DC.

22. Action
- Promote the first Windows Server 2008 R2 DC.
- Move relevant roles
– DHCP
– DNS
– WINS
- Transfer FSMO
- If needed, point relevant applications to new DC.

23. Names and IP addresses
Is it simpler to
1. New DCs, new
keep the old DC’s Simplest
names, new IPs
name and/or IP
address?
2. New DCs, new Medium
Possible options: names, old IPs complexity
3. New DCs, old May be more
names, old IPs complex

24. New DCs, old names and IPs
Option 1: Problems:
- Demote old DC - What do you do with the
Give name and IP to the FSMO roles and other roles
new server on the old DC?
- Promote new server to - DNS, DHCP etc. may not
DC (+GC) function for a while.

25. New DCs, old names and IPs
Option 2:
- Give new server a temp. name and temp. IP
- Promote new server to DC (+GC)
- Move DNS, DHCP etc.
,
- Rename old DC to alt. name and assign alt. IP
- Rename new DC to old name, assign old IP
- Transfer FSMO
- Demote old DC (you may want to wait a few days)
To rename a DC – you must use netdom.exe

26. Check everything is ok
Always wait for KCC (15-30 minutes).
If replication topology is complex – wait for
replication for as long as it takes.
Before you demote old DC, make sure new DC is
functioning:
- Check replication
- Check SYSVOL
- Check events

27. Time synchronization
PDC Emulator of the Forest Root
Domain is responsible for time
Servers and
keeping.
workstations pull
If not properly configured – Event ID 12
(W32Time).
from DCs.
http://support.microsoft.com/kb/816042
PDC Emulators of
other domains in forest Never pull time
pull time from FRD DCs pull time from host if using
PDCE. from PDCEs. virtualization!

28. Time synchronization
- Configuration for FRD PDCE:
w32tm /config /update /manualpeerlist:"timeserver.iix.net.il"
/syncfromflags:manual
net stop w32time && net start w32time
w32tm /resync
- Check HKLM/SYS/CCS/Services/W32Time/Config >
AnnounceFlags = 10 (Decimal)
- If you get an error, check that UDP port 123 is open
through the FW:
portqry -n timeserver.iix.net.il -e 123 -p udp

29. Some additional tips
- Never clone a DC operating system!
- Remember Windows Server 2008 R2
issues a random computer name by default
- Do NOT disable IPv6
http://support.microsoft.com/kb/929852
- Configure Windows Update
- Secure the server(s)

30. Some additional tips
- Configure Anti-Virus exclusions
http://support.microsoft.com/kb/822158
- Configure backups
- Do not use snapshots for virtual DCs
- Do not pause/resume virtual DCs
- If on VMs, exclude DCs from Live
Migration or vMotion

31. Removing old DCs
Take your time If demoting is
to test. If all = ok, demote unsuccessful –
old DCs one by one consider forcing
(dcpromo.exe). (/forceremoval)
Consider shutting
down old DC(s) for If demoting was unsuccessful – you must
a few days (the clean AD from old DC remains
“who did it???!” (ntdsutil.exe)
effect). http://support.microsoft.com/kb/216498

32. Raising DFL and FFL
Domain Function Level:
- Active Directory Users and Computers
Check version:
dsquery * “dc=contoso,dc=com” -scope base -attr msDS-Behavior-Version
(should be 2 for 2003, 4 for 2008 R2)
Forest Function Level:
- Active Directory Domains and Trusts
Check version:
dsquery * “cn=partitions,cn=configuration,dc=contoso,dc=com” -scope base
-attr msDS-Behavior-Version
(should be 2 for 2003, 4 for 2008 R2)

33. Demo
- Adding the first Windows Server 2008 R2 DC.
- Removing the old Windows Server 2003 DC.
- Raising DFL/FFL.

34. Conclusion
Upgrading your
AD to Windows
Server 2008 R2 is Plan and test
important even if before you move.
you do not plan
to use any of the
benefits.
Upgrading is not Verify and clean More sessions on
rocket science. after you move. AD will follow…