Does OnStart gets called from WebRole.cs in the case of Upgrade deployment?
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Yes, I believe it runs on every reboot. When the machine is rebooted, reimaged or upgraded by Microsoft, the OnStart will run.

ryan1234
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Yes, it does indeed. The problem was due to some code in OnStart that was throwing exception and was getting caught in the exception handling block making rest of the changes not getting executed. This made me feel, OnStart is not getting called at all. – Hrishi Nov 03 '14 at 23:58