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Server service hangs and is unable to stop on Windows SBS 2003

In our office we are running a Small business server 2003. One of our applications runs from (and keeps it's data in) a shared folder on the SBS-server. We are having a problem that the application suddenly won't start. I have even tried to start the application locally on the server, but the .exe file seems sort of locked. Trying to start it fails (not responding). I have then tried to restart the service called "Server", which handles file sharing. This service fails to stop.

Eventually I just have to restart the server to get it right. This have happened a bit too often lately and it is bothersome to have to restart the server all the time. I hope someone can help me.
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plug1
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What is the application? What service pack are you running on the server?

TBH I'd be speaking to whoever developed the software you use in the first instance..
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Well. It is our accounting-software. But I don't think it is really related to it. I think the sharing is failing, causing the file to hang. After a bit of testing, I have the feeling that this especially happens after I have logged on to the server from home (using VPN).
So when the application fails, can you not access any other shared files or print through the server?
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Well.. not quite. The application can fail with the shared files working and the printing working. But sometimes the shared files stop working and printing fails. I don't really think it is linked to the application failing. The application fails a lot more often than all failing.
In that case I wouldnt be looking to the server service as a problem. HAve you monitored processor usages, memory and virtual memory usage when this happens?
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No, I haven't. How would you recommend I do it? After the problem has started? Monitor with what?
The quickest way to do it is with task manger, have a look at the server while its working, watch it for a while to see what is "normal" in terms of memory and processor useage and add an extra column for virtual memory. When it next starts happening take another look at task manager compare and contrast, also if anything is running high then go to the processes tab and order them with the highest first (mem or processor useage) this will tell you whats at the root of the problem.

Alternatively you can monitor it over a period of days using performance monitor but I prefer the easy way.
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