Github user aledsage commented on the pull request:

    https://github.com/apache/brooklyn-server/pull/150#issuecomment-222639688
  
    Speaking to @bostko off-line, it seems that things are more complicated 
when it comes to a windows script kicking off a reboot. The reboot might not 
happen immediately.
    
    The install script that triggers the reboot might return, and then we'll 
start executing the subsequent scripts. But in the background, the windows VM 
is doing stuff and is about to reboot. So it's a race as to which script we 
will be executing when the reboot actually happens. If it's not the install 
script, then the configuration option added in this PR will not be enough. The 
provisioning of the windows blueprint might then fail at the post-intall step 
(or uploading of runtime-files, or customize or launch, etc).
    
    If it is a subsequent step that fails, we really would need to retry it. 
But it might well not be idempotent! 
    
    It would be good to have a more holistic approach to fix this (and/or a 
consistent approach applied to all the steps).
    
    Perhaps we need a "reboot expected" configuration option. This would be 
similar to `install.reboot.required`, but would not trigger the reboot. Instead 
it would wait for something that looks like a reboot (i.e it going offline and 
then back online), before continuing with the subsequent tasks.
    
    @nakomis what are your thoughts?


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