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We have a custom service that runs on Windows Server 2008 R2 64 bit. It has startup type of "Automatic". However, after a reboot, the service does not start automatically. It does start if we manually start it from the service control panel. What are some possible causes of this, and how can I debug it? I examined the even log and didn't see anything special.

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Sounds like a service dependency issue to me. What type of service is it? If you can think of any dependent services that must start first, add them to the dependency list on service properties from services.msc

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You can try to modify the log on user. Right click on the Windows Services item then select "properties", click tab "log on", in "log on as" select "This Account" then fill in the system Administrator user name and password. It's possible the account assigned to the service does not have the correct permissions to fulfill the functionality of the service. For example, if the service has to write data to a drive but the id used for the service does not have this permission, therefore causing the service to fail upon start up.

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Similar to floyds answer, this could be because of a service dependency, or because a resource it relies on is not ready during boot (like a network resource). You could try setting its startup type to delayed start to see if that helps.

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Delayed start may only be an option if the OS is 2008 or later. – Mark Jun 19 '14 at 21:33

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