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Over the years there have been a number of newsgroup posts about using System Cloning with IIS. Some customers have cloned the image and then found that IIS service will not restart on the cloned image when it boots up.
There are a number of issues that may have an impact here. The most common one to be aware of is that fbreseal.exe does not support cloning an image more than once. Cloning an image numerous times can lead to data loss and image corruption of user settings, IIS & database settings, domain memberships and local & group policies.
Even on image sealed just once the IIS service may not start, due to a timing issue with services restarting on the cloned image. Brad Combs explained it this way in a newsgroup post: