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So yesterday I asked this question: How to create a single image of Windows Server 2008 R2 to use on a Azure Virtual machine

I was told by multiple sources I need to run sysprep against the machine, which I did with the following settings: enter image description here

The machine will not boot back up now.

So a system engineer drove to the Colocation and reported first: "There was windows 2008 r2 enterprise setup process which I stopped by manually rebooting server not sure whats you've been doing. Server is coming back up now"

And then he said: " I'm getting windows server installation prompt?"

What is the server installation prompt here, does it want the windows server installation CD? I do not have one, its an ISO, do I need to burn it, seriously?

The following was suggested to me from this Serverfault question:

"just go through install prompts of windows and use disk2vhd without sysprep. Microsoft built sysprep into disk2vhd, don't know why they said those things in that article"

I do not fully understand this statement, is there any opportunity left to cancel sysprep process I kicked off?


So the question I was trying to get an answer to was if, once you ran Sysprep with "Enter System Out-of-Box Experience (OOBE), is there anyway to cancel the Sysprep process, the answer is No:

"Sysprep restores your system back into the disk image when you first run the computer... All data will be lost since the old disk image have been overwritten by the default disk image or factory default image"

Referenced here

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YOU RAN SYSPREP ON A PRODUCTION MACHINE?! Dear lord, you need to learn reading manuals – Mathias R. Jessen Jan 16 '15 at 20:53
Also, you did this on a machine you don't have remote console access to? Lesson number 3 or 4, right there. IP KVMs are cheap and out of band management (IPMI/iLO/iDRAC/whatever) comes standard these days. For a reason. – HopelessN00b Jan 16 '15 at 21:07
Its not really production anymore, it is my bankrupt startup and I am just migrating to Azure for cheaper hosting – Brian Jan 16 '15 at 21:11
up vote 6 down vote accepted

From the appropriately named (and fairly SEO-friendly) TechNet article "What is Sysprep?":

[...] Sysprep also enables you to prepare an image to be delivered to a customer. When the customer boots Windows, Windows Welcome starts.

Then, follows a general notice about appropriate usage:

Sysprep must be used only to configure new installations of Windows. You can run Sysprep as many times as required to build and to configure your installation of Windows. However, you can reset Windows activation only up to three times. You must not use Sysprep to reconfigure an existing installation of Windows that has already been deployed. Use Sysprep only to configure new installations of Windows.

The third introductory paragraph even dives into why that is:

If you intend to transfer a Windows image to a different computer, you must run sysprep /generalize, even if the computer has the same hardware configuration. The sysprep /generalize command removes unique information from your Windows installation, which enables you to reuse that image on different computers. The next time you boot the Windows image, the specialize configuration pass runs. During this configuration pass, many components have actions that must be processed when you boot a Windows image on a new computer. Any method of moving a Windows image to a new computer, either through imaging, hard disk duplication, or other method, must be prepared with the sysprep /generalize command. Moving or copying a Windows image to a different computer without running sysprep /generalize is not supported.

Sorry to say this, but ... you shouldn't have done that, it's time to restore from backup

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Any suggestions on restoring from backup if I cannot boot the machine? I have Windows Server Backup vhds of the server but if I cannot boot the server I am not sure how I can do this – Brian Jan 16 '15 at 21:08
Just finalize the Windows Welcome configuration and grab them from the disk, sysprep reconfigures the OS and pertaining files, but leaves the rest of the file system alone. You will need remote console access, remote hands or physical access to the machine in any case – Mathias R. Jessen Jan 16 '15 at 21:35
You didn't really answer my question and you were kind of rude too. But have some points anyway! – Brian Jan 20 '15 at 5:23
Yup, sorry about that. It really is about getting my point of "don't just do, read the docs first" across, nothing personal. Thanks for the points! – Mathias R. Jessen Jan 20 '15 at 12:47
you are welcome ;) – Brian Jan 20 '15 at 22:06

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