IIS v7 VMWare Cloning for Test Purpose

iisiis-7vmware-vspherewindows-server-2008-r2

We have production Server 2008R2 VMs running IIS v7. The app pools have their own AD service accounts (not anonymous IUSR).

Will there be issues cloning these IIS machines into a stage environment? I'm assuming we'll have to sysprep them, which maybe difficult to automate (we're planning to do the cloning via PowerCLI and the nic setup via PowerCLI as well.)

As far as I can tell, the only real issue with cloning IIS v7 is if anonymous account was still in place.

Best Answer

Yes. You are correct you will need to SysPrep (Sysprep, Machine SIDs and Other Myths) your servers.

You can apply your Customizations (i.e., SysPrep settings) when cloning your machines using PowerCLI like so:

C:\PS>$specification = Get-OSCustomizationSpec -Name WindowsSpec

New-VM -VM VM1 -Name VM2 -OSCustomizationSpec $specification


As for how SysPrep will effect IIS, I got conflicting answers doing a bit of research. The challenge I always have with SysPrep is that, I know it changes a lot of things during the generalize process but I always have difficulty finding documentation on what exactly it changes. It looks like that in Windows Server 2008, IIS is now supported by SysPrep (Sysprep Support for Server Roles) with the exception of instances where encrypted credentials have been stored the Applicationhost.config file. Previously with Windows Server 2003 and IIS 6.0 SysPreping was not a supported configuration (KB326779).

You take a good hard look at Web Deploy which will probably accomplish what you want to do with IIS in a more elegant fashion.

You really should follow @HopelessN00b's advice and test and document this process prior to committing to a plan that requires SysPrep.