Microsoft Windows 2000 & 2003
Domain to Windows 2008 Upgrade Procedure
& Things to Know in General About Server 2008
Prepared by Ian Matthews September 21, 2008,
last updated October 6, 2008
Server 2003 upgrade process, I have attended no Windows 2003 to 2008
Microsoft presentations (live or on-line). This is very
unusual for Microsoft but the process is easier than it was
from 2000 to 2003.
I have now completed five Sever
2008 installs, some on existing domains, some on new domains and I
have learned a few things which will make your life easier. I
primarily create this type of documentation for me to use on future
installs but I will do my best to not gloss over what I think are
NOTE: This process below
is offered with no guarantees and we accept no liability.
To keep an otherwise complex
process simple, it is provided in a terse point form.
Windows Server 2000 / 2003 to 2008 Domain Upgrade
DNS servers to "scavenge" every 7 days
If you are
upgrading Window 2000, make sure they are running
Service Pack 4
Make sure the servers being upgraded
have 1GB of RAM or better (512MB works but it is damn slow).
HERE for Microsoft's complete list of official hardware
Make sure the
rest of your hardware, software, and BIOS can run Server 2008 by
downloading the Microsoft Deployment 2008
I have installed and run this
tool on my 32 bit Vista domain connected PC and then had it
check my servers which I planned to upgrade to 64 Bit 2008.
It is easy to use, quick, and provides understandable output.
On 2003 there was a
great little to
which would tell you all about your situation but 2008 has no
such tool built in
If you are concerned with your software, you
can user Microsoft's searchable
2008 Compatibility Catalog .
Note that only "local" (LPR) and "Standard
TCP/IP" printer ports work under 2003 and 2008
Flash update EVERYTHING you can; BIOS, FRU/SDR,
If you are upgrading and existing
domain. try to first upgrade has server that has the PDC Emulator and Domain
Naming Master & RID Master FSMO's.
STOP and DISABLE any services you don't need
(i.e. the FAX Service, Windows Audio...)
Take a backup of your SYSTEM STATE (and
everything else, if you can find the time).
I use NT Backup for this because it is quick,
easy and NEVER lets me down
sadly, NT Backup is been replaced in 2008
with some massively limited garbage called
Windows Server Backup .
if you are upgrading a print server,
and you have 30 minutes, backup your
printers using PRINTMIG 3.1 which you can get
set your Domain/Forest to the highest level
possible via ACTIVE DIRECTORY DOMAINS AND TRUSTS. Click the
pictures below if you are confused.
for the DOMAIN LEVEL, right click on the
domain and for the FOREST LEVEL, right click on the FOREST.
HERE for more details
you must allow time for these changes to
replicate to the other servers on your domain/forest. For
most smaller networks this will be less than 10 minutes, if not
Make sure you have an internet
connection on at least one of your network cards because the install
process will check for critical updates during the install.
IF you have
customized Active Directory rules (i.e. Modified Group Policy .ADM
file to include blocking of more hard drives than A: B: C: D: [which
is available by default] then you need to migrate your Active
Directory ADM files to the new ADMX format. This is a complex
area which is fully explained
Reboot and do a common sense check:
resolve any service errors
check for major event viewer errors relating to key AD
components like FRS and DNS
verify their is a pile of hard
drive space (like 1GB+)
ACTUAL UPGRADE STEPS:
Insert the Windows Server 2008 DVD and go to
the \SOURCES folder. You need to run three Adprep commands
(separately but in the order shown) to update the old 2000/2003
schema's to the most current:
Adprep /domainprep /gpprep
Some of these are fast and some are take
some time. I have not had a failure or error yet so just
give it the time it needs to upgrade.
If you are planning to upgrade your domain
Windows to 64bit Windows, you must use 32bit ADPREP (i.e. go get
a 32Bit Windows Server 2008 disk, to complete this step.)
If you try to use your 64bit version, not much happens.
You can not a "Upgrade Server 2003 32 Bit to
Server 2008 64 Bit". You must do a bare metal install.
If you do have ADPREP weirdness or errors,
you will find
If you want to the option to have a cool new
Server 2008 feature called a READ ONLY DOMAIN CONTROLLER, you must
also run the following:
If you choose not to follow step two (which I
usually skip) will see the following error message which you can
safely ignor during the install process:
Force replication to all DC's via Active
Directory Sites & Services
and then wait a
MINIMUM of 20 minutes before starting the Windows 2008 upgrade.
If you did not wait long enough you will see the following error
Disable all anti-virus and non-windows applications like
event log trackers and 3rd party FTP servers
IF YOU ARE
insert the W2008 DVD, let it autoplay, and select INSTALL then
ARE INSTALLING ON A FRESH SERVER: Boot off the W2008 DVD and
answer the obvious questions
the upgrade process which will take less than an hour for most
No, you will NOT be asked for
a "CD KEY". You will have to enter the key AFTER the
install is complete as part of the "activation" process.
See the end of
THIS if you want more information.
You may see "This computer has
dynamically assigned IP address(es)..." relating to your network
configuration. Personally, I disabled IP v6 along with all
unused Network Cards, then set static IP's on the only in-use
cards but still had this message.
You will almost certainly see
"a delegation for this DNS server cannot be created because the
authoritative parent zone cannot be found...". I
understand this has to do with rDNS (reverse lookups) but my
servers have rDNS configured and I still see this error.
This can be safely ignored.
After you have completed your install, you will
be presented with the Initial Configuration Wizard. You should
click on and set, ALL five items in section 1 and 2. There are some
important things to note:
I strongly recommend you approve sending
I strongly recommend you NOT approve
Automatic Updating. You should choose, "Automatically
download but do NOT install".
If you choose the default setting of
"Automatically Download and Install Updates", your server
WILL reboot itself sometime after 3am when updates are
complete. Not to mention that YOU should be in control
of your servers updates, not Microsoft. I recommend
you wait 2 weeks after release before you install server
updates; this gives Microsoft enough time to correct or
remove "bad" patches.
You should check for and
install all Windows Updates immediately
After the upgrade is complete, check event viewer for key
errors - ignore Event ID 1931
Check DNS and AD replication
Check DEVICE MANAGER (which is now
under SERVER MANAGER, DIAGNOSTICS, DEVICE MANAGER) to confirm all of
your hardware is functional under Server 2008.
Unlike its predecessors, Server
2008 does not have "Support Tools" (from the DVD) or a "Resource
Kit" so you have nothing extra to install.
Unlike its predecessors, you do not have to copy
the install files from the DVD to a directory on your server (i.e.
the i386 directory) on Server 2008.
Like Vista, the install files are stored in the Windows\WinSXS
You will need to go to System
Properties to manually activate Server 08.
Re-enable Antivirus and another of
3rd party services disabled before the upgrade
usual system maintenance routine
temp files and old profiles, emptying the Recycle Bin...
Most sub 500 seat companies will
want to enable Automatic Defragmentation. To do this just
click START and type DEFRAG in the search bar and do what is
Most companies will want to spend
the 10 seconds to enable Shadow Copies (if they are not already
enabled) by right clicking on any drive and selecting the Shadow
astounded at how many IT "Professionals" either don't use or
don't know about Shadow Copies. They are SOOOOO easy to
setup and use. They will save you many many hours
performing tape restores. Read
THIS if you
want more details
Server 2008 includes the
ability to revert an entire partition to a PREVIOUS VERSION
relevant steps for all DC's
After all DC's are upgraded, increase "Functional Mode" via Active Directory
Domains & Trusts to 2008 NATIVE MODE. See Step 11 in PreWork near the top of this page.
Things to Know About Windows Server 2008:
You can/should read about the 2008
Windows Recovery Environment at the bottom of
If you ran
IIS 5 or 6, you are in for a surprise... lots of changes:
FTP is still available as a ROLE FEATURE under IIS but there is
a new FTP for IIS7 from Microsoft you can download
Desktop's "Console Mode"
has changed to /ADMIN mode. Click
HERE for details.