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How to Sysprep Windows Server 2008

2008-10-15 james 50 comments

I was going sysprep a base image of Windows Server 2008 this morning and followed my own instructions on sysprepping Windows. I went to the installation DVD and couldn’t find sysprep. A quick google later and a bit of poking around revealed that sysprep is now installed by default on Windwos Server 2008. You can find it at:

c:\Windows\System32\sysprep\sysprep.exe

The experience is also streamlined considerably. Simply run sysprep.exe above and you are presented with:

Check the “Generalize” checkbox (regenerates system SID), change the Shutdown Options to “Shutdown”, and click OK. The system will go through the sysprep process and shut itself down. You can now create cloned servers to your heart’s content simply by creating linked servers and booting the clone as originally documented here.

UPDATE: Benjamin Chau noticed that SIDs weren’t being regenerated. Turns out that you need to check the Generalize checkbox to make that happen.

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Comments (50)

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#1 | Written by Amber about 16 years ago. Reply

Thank you so much! Such a simple solution to hours of aggravation!!
#2 | Written by Nick Marson about 16 years ago. Reply

Thank you once again James!
#3 | Written by Gary Grudzinskas about 16 years ago. Reply

Way to keep it simple James.
#4 | Written by Benjamin Chau about 16 years ago. Reply

I went through the same procedure. I even so far as using this VHD created as a base of a Differencing disk which I built with multiple W2K8 server. The problem is that when I use PSGetSID to look at the servers. All of them share the same SID. That caused a major problem on some security operation.

Anyone has similar experience?
#5 | Written by James Kovacs about 15 years ago. Reply

@Benjamin – I just checked on my VMs and you are correct – the SID isn’t regenerated. I looked around and found that you need to check the "Generalize" checkbox to regenerate the system SID. (Updated above.)
#6 | Written by Roland about 15 years ago. Reply

It’s OK for 32bit.

And x64 version?

Ooops…
#7 | Written by James Kovacs about 15 years ago. Reply

@Roland – The same procedure works for x86 and x64. Are you having an issue with sysprepping a 64-bit OS?
#8 | Written by Ron about 15 years ago. Reply

How can I bypass the activation for a clone?
I need to create several VMs for development purposes.
Thanks
Ron
#9 | Written by James Kovacs about 15 years ago. Reply

@Ron – As far as I know, you can’t bypass activation when sysprepping. The Product Keys that you get with your MSDN Subscription can activate a lot of virtual machines for dev/testing purposes. I don’t know for sure, but I believe that you can call MS product support to request additional activations if you legitimately hit your license activation limit.
#10 | Written by www.google.com/accounts/o8/id?id=AItOawnVK1kfgad_46i5-IJgmsgtlJYhaJAL3XY about 15 years ago. Reply

2008 Server Enterprise 64bit
I tried
C:\Windows\System32\sysprep\sysprep.exe
and
C:\Windows\SysWOW64\sysprep\sysprep.exe
and both of them giving me a message:

======
System Preparation Tool 3.14
——
The 32-bit version of OPK tools does not support WOW64.
Please use the 64-bit version of the OPK tools instead.
======

🙁

Alex.
#11 | Written by joel about 15 years ago. Reply

james, great post.

i googled "sysprep 2008" and the first entry was

http://briandesmond.com/blog/how-to-sysprep-in-windows-2008/

… what a joke.

i almost started that process, and i thought, "wait, i should probably check at least one more link just to see if there wasn’t really a much much simpler solution"

thanks for this.
#12 | Written by Pedro about 15 years ago. Reply

Thanks James!

As far as Joel’s comment on the briandesmond post goes, those steps are still necessary if you’re deploying on a larger scale so that it is more automated as they are there to demonstrate how to generate an answer file. Unless you want to be manually going through the initial setup (Time-zones, etc..) for multiple servers.
#13 | Written by Deeksha about 15 years ago. Reply

Hello,
This info was really useful. But the link you mentioned above in your description doesnt exist.
“I was going sysprep a base image of Windows Server 2008 this morning and followed my own instructions on sysprepping Windows. ”
AND
“You can now create cloned servers to your heart’s content simply by creating linked servers and booting the clone as originally documented here.”

Due to this i am not clearly not understanding the process. Can u help me with the contents ???

Thank you
#14 | Written by Vimal about 15 years ago. Reply

Thanks a lot.. it’s is working fine.
#15 | Written by Richard McBride about 15 years ago. Reply

Can anyone tell me how to run Sysprep on Windows 2008 Server Core?

Thanks
#16 | Written by Walid AlMoselhy about 15 years ago. Reply

Way to go man… I was wondering where the hell did they hide this tool, works also on windows server 2008 R2… .saved me a lot of time buddy
#17 | Written by Sanjay about 15 years ago. Reply

The article on this link http://briandesmond.com/blog/how-to-sysprep-in-windows-2008/ highlights answere file generation using WSIM in WAIK.

You will use this to generate answere file for WINDOWS 7 or WINDOWS 2008 machines from Windows 2003/XP/Vista client machine.

There has been lot of negative comments on Brians article and there are lot of guys who have misunderstood the new way of making Sysprep answere files for Windows 7 and W2K8 o/s.
#18 | Written by Yassen about 15 years ago. Reply

Hi James, the link to an older article of yours, you mention above (http://jameskovacs.com/2008/10/15/how-to-sysprep-windows-server-2008/2007/07/11/How-To-Sysprep-Windows) is broken. Obviously, it must be http://jameskovacs.com/2007/07/11/How-To-Sysprep-Windows; hope you can fix it easily.
#19 | Written by James about 15 years ago. Reply

@Yassen – Thanks for the heads-up. Links fixed.
#20 | Written by pie8ter about 14 years ago. Reply

On the GUI above, when you select the “OOBE”, check the “Generalize” box and select the “shutdown”, you are basically doing this:

sysprep /generalize /oobe /shutdown

When you reboot the PC, you will start from the generalize phase followed by OOBE. The generalize and OOBE installation phases will prompt you with lot of questions. It’s not a big deal if you only have one or two PCs to clone. You can sit in front of the PC and answer the questions. For mass deployments, an unattended answer file will be a huge help. This is true in Windows XP and 2003, too. For XP and 2003, setupmgr.exe is used to create the unattended answer file called “sysprep.inf”. In Windows 7 and 2008, you use the WAIK to create the unattended answer file. The setupmgr.exe is like a wizard in which you answer series of question and it will generate an unattend.txt file. WAIK is modular and requires you to import the install.wim before creating the unattend.xml file.

Brian Desmond was showing how to generate the unattended answer file using WAIK in the following blog:

http://briandesmond.com/blog/how-to-sysprep-in-windows-2008/

I don’t know who Brian is but calling his blog a joke is completely unprofessional.
#21 | Written by OBXMAN007 about 14 years ago. Reply

I agree whole-heartedly with pie8ter – only a feeble-minded little numb nut would put down a fellow I.T. brother – you are a disgrace to all of humanity. Brian’s method is absolutely necessary for creating the unattend.xml needed for mass deployment. I would use many expletives to condemn your behavior, but I will refrain and not get on your low, slime-ball level little child.
#22 | Written by James about 14 years ago. Reply

I’m not one to censor opinions, which is why I’ve published the above comments. I’m sure both my post and Brian’s posts have value. I’m glad that people can find both and decide which method is best for their environment/situation. I would ask that commenters stop the name-calling and go back to focusing on the technical issues. I will delete any further comments on this blog post that do not focus on technical merits or issues.
#23 | Written by Uncle Joe about 14 years ago. Reply

Hi James,
i have a problem using sysprep on a 2008. i ran sysprep /generalize /oobe /shutdown. when the server comes back, it gives response “Windows could not update the computer’s boot configuration”. did you ever hear something about this issue? and perhaps, do you have any solution?
thank you
#24 | Written by James about 14 years ago. Reply

@Uncle Joe – No, I’ve never encountered this error. I would ask on serverfault.
#25 | Written by alaa about 14 years ago. Reply

dear james,
i need to ask you concerning my issue which is , i made installation for windows server 2008 on hp proliant BL 460 blades, but the problem i used the cloning method but i didnt take the CID for each blade which can and for sure affect on the active directory that will run soon on these blades, so what shall i do concerning that?i must run sysprep on each one or also by cloning method? please i need your help as soon as possible.
#26 | Written by Travis about 14 years ago. Reply

Also, if you have forgotten to check the generalize button you can poke around the internet and download NewSid.exe. It use to come packaged in SysInternalsSuite, but they have since removed it from the suite. I have have used it several times in my VM’s and it works like a charm.
#27 | Written by James about 14 years ago. Reply

@Travis – The reason that NewSID.exe is no longer available in the sysinternals Suite is that it is not necessary. Check out Mark Russinovich’s detailed analysis and explanation of why NewSID is basically a NOP and not necessary. (N.B. Mark was the original author of the NewSID tool.)

http://blogs.technet.com/b/markrussinovich/archive/2009/11/03/3291024.aspx
#28 | Written by James about 14 years ago. Reply

@alaa – I’m not a sys admin and don’t pretend to be. I know enough about system administration to manage my own small network and set up virtual networks for software development. I would recommend asking your question on serverfault where you can get a much better answer from real sys admins who have dealt with this problem before.
#29 | Written by Dan about 14 years ago. Reply

James,
Thank you for sharing your expertise. Your article has been extremely helpful to us.
#30 | Written by Perry about 14 years ago. Reply

Hello, James. Thanks for this discussion; it’s been very helpful.
So, I had two questions. I am creating clones of a master Virtual machine, WS 2008 R2 64 bit, that is running on Citrix Xen Center.
So, I run Sysprep on the master before making a clone.
1) Do I need to run Sysprep before each clone I make of the master? Or only once?
2) Is it possible to turn the master on again after sysprepping and cloning it, and update it or add applications, if necessary, and then clone it again? If I can clone it again after altering it, do I have to run sysprep again?
Thanks for your time.
- #31 | Written by James about 14 years ago. Reply
  
  You only need to sysprep once, but will need to sysprep again if you modify the image. Note that if you have VMs based off this image, modifying the base image will not work.
#32 | Written by Mark about 14 years ago. Reply

I am cloning Windows Server 2008 R2 64-bit VM’s and found that newSID.exe corrupts the images. So I tried out SYSPREP using the OOBE and Generalize settings. After the reboot and going through the initial setup I ran psgetsid only to find out that the SID had not changed.

Am I missing something?

Thank you!
- #33 | Written by James about 14 years ago. Reply
  
  Turns out there is no need to change the SID. Mark Russinovich (creator of NewSID) discusses why duplicate SIDs are not actually a problem, contrary to what he initially thought: http://blogs.technet.com/b/markrussinovich/archive/2009/11/03/3291024.aspx
#34 | Written by Will about 14 years ago. Reply

James,

Thanks for the article. I was curious to know if sysprep will include imaging the current networking drivers, and some other various drivers that are installed after my first initial installation.

I am starting off with a basic install of 2008 x64 and then installing the necessary drivers / components and finally then running sysprep. Will my drivers be included with the image?
- #35 | Written by James about 14 years ago. Reply
  
  Yes, your drivers should be included as sysprep is typically the process that OEMs such as Dell use to install the OS and drivers before shipping you your computer. When you turn on your new computer for the first time, you get the usual “Starting Windows for the first time…” experience.
#36 | Written by Bryan Lawrence about 14 years ago. Reply

Thanks for the info. I have found it helpful so far, but I have a couple of questions about sysprepping in my environment. Server 2008 R2 x64 – citrix XenApp5. I’m going to use XenappPrep on server “A” to remove all specific citrix info from that server. That process should basically take it out of the farm as far as I can tell. After doing the XenAppPrep, I plan to run Sysprep, and then shut that server down, then create an image of it by booting to my shadowprotect cd and using the image backup function. Then I plan to copy that image to another server and my hopes are that I can get it up and running, on the domain and in the farm without any software installs necessary. I then want to be able to bring server A back up as a server in the domain and also in the farm. My questions are…
1. Do I need to remove Server A from the domain before I sysprep it?

2. If I don’t have to remove it from the domain before I sysprep it, will I be told that Server A is already a member of the domain?

3. If I have to remove it from the domain will I be able to get it rejoined to the domain before my XenAppPrep kicks in and tries to join the farm? I know this question may be a bit off topic but it is related to the whole sysprep process and maybe someone has been through it.
#37 | Written by sudhakar about 14 years ago. Reply

Hi James,

I did sysprep in my windows 2008 R2 VM. And after sysprep, i see that the new image is not booting up. I followed all the steps correctly.

During bootup i see one cmd prompt window opens up during setting up services screen, throws some red colored text in the cmd prompt and then reboots. After reboot also same issue continues. Could you pls let me know why the sysprepped image is not booting up? how to figure this out?
#38 | Written by Shery about 14 years ago. Reply

Thanks Jack,
That helped.
— Shery
#39 | Written by Ryan about 14 years ago. Reply

I’m a little confused since this is the first time I’m trying to use sysprep. I hope you can clarify how to use the sysprep tool for cloning an OS. I want to take an image of a Windows Server 2008 and copy it onto other servers. I have already created the image of the server. Do I load the image onto another server and then once loaded and installed, I run sysprep to change SIDs, computer name, activation code, etc.?

Or do I run through sysprep steps first on the host I want to clone, then create an image, then copy the image to a server and the sysprep will guide me through the first time booting up?
- #40 | Written by James about 13 years ago. Reply
  
  You set up the initial server, run sysprep to re-seal the OS, and then transfer it to another server. Note that the servers need to have identical hardware (or close to it) otherwise the sysprepped image won’t boot.
#41 | Written by William Hatten about 13 years ago. Reply

I trying to sysprep a 2008 server and use Imagex to get the image file but it keeps failing as it does not find the image file. Could you please help with that process.
#42 | Written by Joseph about 13 years ago. Reply

Hi James,

i did a sysprep using the sysprep in windows 2008 R2 sysprep.exe in the system32 folder. I clicked (OOBE) and shutdown option i selected “Quit” and i rebooted my machine manually . It prompted me to change password when i entered my old password it said “Access Denied” . What exactly happened ? i am lost , and i did not clone the syspred image from that machine as i was afriad it would happen to all my machines if i cloned it. Would you advise me ? Thanks.
#43 | Written by NoCertsJustLife about 13 years ago. Reply

A note to the cloners – Failure to change the SID, although not required, will make a WSUS database fail. Near as I can tell WSUS (Windows Server Update Services) has a SQL database that is key’ed on the machine SID and it ignors domain SID.

If you clone server “A” to make “B”, “C”, etc., you may only find server “A” in your WSUS database. If you group your servers in WSUS to allow/deny selected updates, you may be selecting all type “A” servers by selecting just “A”. Always “Generalize” your clone source, or find and use NewSID.

And oh, by the way, if your source computer is already joined to a domain, remove it from the domain (make it a workgroup computer) before SYSPREP. This is another source of pain.
#44 | Written by Hayden Hancock about 13 years ago. Reply

I’ve tried performing this method in a virtual environment (VirtualBox). Everything seems to work fine except that my VHD changes what I had in my domain. For instance, I used company.com as my domain but after sysprep, it put that into the WORKGOUP field.

Any suggestions on what I am doing wrong? Thanks!
#45 | Written by David Nilson about 13 years ago. Reply

@NoCertsJustLife
You are correct that duplite WSUS SIds will cause one and only one of the machines with duplicates to show up in WSUS at one time.
But thats a different SID and is easily solved by deleting the WSUS SID fro mthe registry, it will auto-create on next boot.
Try this in a .CMD file on an effected machine or in logon scripts:

net stop wuauserv

REM — Clear out history and downloaded updates – start Fresh
cd %windir%\SoftwareDistribution
del DataStore /q
rmdir Download /S /Q

REM – Normal
:SUS_normal
Reg DELETE “HKLM\Software\Microsoft\Windows\CurrentVersion\WindowsUpdate\Auto Update” /v LastWaitTimeout /f
Reg DELETE “HKLM\Software\Microsoft\Windows\CurrentVersion\WindowsUpdate\Auto Update” /v DetectionStartTime /f
Reg Delete “HKLM\Software\Microsoft\Windows\CurrentVersion\WindowsUpdate\Auto Update” /v NextDetectionTime /f

REM – d.a.n. To regenerate SUSclientID
reg delete “HKLM\Software\Microsoft\Windows\CurrentVersion\WindowsUpdate” /v SusClientId /f

net start wuauserv

:SUS_end
wuauclt /resetauthorization /detectnow /reportnow

:SUS_End2
#46 | Written by David Nilson about 13 years ago. Reply

@Hayden Hancock
That is the EXPECTED behaviour of Sysprep . Read “What is Sysprep” at:
http://technet.microsoft.com/en-us/library/cc783215(WS.10).aspx
#47 | Written by Nathan Boyd about 13 years ago. Reply

Thanks James, for the nice concise explanation!

@Hayden: That’s by design. Sysprep returns the installation to the “first reboot after installation” but with the whatever updates installed. Typically any customizations and/or settings will be wiped during sysprep. If you want customization after Sysprep, then look for the link to Brian Madden’s blog above.
#48 | Written by Jeff about 13 years ago. Reply

James, thanks for the article, BUT you make a statement that is not entirely correct – stating it is the same for 64-bit and 32-bit – not necessarily true. For one thing, there is a Hotfix / patch of sorts that ‘allegedly’ puts on the 64-bit Sysprep tool and the accompanying deploy.cab file for 64-bit versions (especially W2k3 R2 64-bit; the install of the w2k3 o/s does not automatically install sysprep); next, for whatever reason, W2k8 also does NOT always install sysprep – don’t ask why – i’m not sure. So, there are some subtle syswow64 differences and along those lines; wow6432 also maybe?

AND, last but not least, you never answered “Alex’s” comment, which is the issue I am having:

2008 Server Enterprise 64bit
I tried
C:\Windows\System32\sysprep\sysprep.exe
and
C:\Windows\SysWOW64\sysprep\sysprep.exe
and both of them giving me a message:

======
System Preparation Tool 3.14
——
The 32-bit version of OPK tools does not support WOW64.
Please use the 64-bit version of the OPK tools instead.
======
🙁

Alex.
#49 | Written by Alessandro Feltrin about 13 years ago. Reply

Hi Folks. I have a question for you … Hope that someone will be able to help me …
My customer has cloned a Windows 2008 Server R2 three times in order to have some lab machines. Now he has attempted to join them to the Active Directory where two Domain Controllers exist. One of them is the machine from which the others W2K8 systems have been cloned with VMWare. Now he gets some problems that seems due to the fact that Systems have the same SID.
Does anybody know a correct way to renew the SID in these VMs? Is not a license problem, customer has the right license for each server. It’s just a need to have more than one system working in a few time.
Hope someone can give me some suggestion
Thanks.
Alessandro
#50 | Written by James about 13 years ago. Reply

Please note that I am a developer, not a sysadmin. I have some familiarity with sysprep for getting testing/dev VMs up and running, but do not purport to be an expert. I would recommend asking your questions on ServerFault.com so that you can get answers from real experts.

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