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I realize this is a very open ended question, and for that I apologize. I just need some ideas.

The service is set to start automatically, and when I reboot the server, the service does not start. I can start it manually, but I shouldn't have to. What are some ways to diagnose this? Where can I look?

I've looked at ISAPI filters, thinking this could prevent the service from starting, but everything checks out so far.

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Have you checked the event logs? –  DanBig Jun 28 '12 at 13:01
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Can you give us a little more detail of your environment? OS/IIS version, any other services running? Sometimes when I've had this it's been because something else had a hold of the port IIS was trying to bind to. –  squillman Jun 28 '12 at 13:16
    
Yes. I don't see anything specific regarding that service. DCOM service had some issues, but that was it. –  Jeff Jun 28 '12 at 13:17
    
@Jeff, You did not find anything in the System Log besides DCOM errors in the relevant time frame? –  Somantra Jun 28 '12 at 13:22
    
2k3 OS @Somantra, I just found one a bit later that said "At least one service or driver failed during startup. Use event viewer to examine the log for details." (which is where I am finding this entry). –  Jeff Jun 28 '12 at 13:29
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