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Provisioning of server...

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When we create a new cloud service I have written scripts that automatically installs IIS and other application on the server using a worker role. This works fine when I re-image the server or reboots the server. But, when Microsoft patches the server and re-provisions the server some part of the scripts fail. I want to debug the script and want to know how can I mimic what Microsoft does while re-provisioning the server after patches are applied. There is an option of Reboot and Re-Image the server  but this doesn't seem to be the same as when Microsoft patches the server. Is there some documentation or someone who can tell me how to mimic re-provisioning a server?


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