Windows Service won't automatically start after reboot?

You likely have a race condition with a dependency. You could probably patch around this by configuring your service to have a dependency on another service ( say tcp/ip ) but what I'd really do is rewrite your service to not need to make this call during the criticial execution path of startup. It should instead periodically attempt to make the webservice call at a later point and log useful messages or send messages to a taskbar utility or similar if there is a problem that needs to be addressed.

Look at question http://stackoverflow.com/questions/1986292, it has a solution to your problem.

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