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Anomalous behaviour in Sockets?

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I am trying to connect to a serversocket on a server which is listening for connections.I connect to the serversocket through the GUI(jsp) which can be used to start,pause,stop the different sub-servers.
Whenever I start the main server using the GUI it makes the socket connection and I get the result status in the GUI which works fine for the first connect.
However when I am in the same session(we are not doing session management as yet for this) and if i start-stop and then try to start the server again.I get an anomalous behaviour.
For the first connect, I can see the latest logs which i had put in the connect code which are fine.But,when I try to connect again in the same session.I get a connection but it shows me the logs which were in the previous version of the code which i had changed and re-compiled.I dont get the result status in the GUI which is expected for the n number of times that I would try to re-connect.
I had also deleted all the earlier class files and made a fresh .war archive for deployment but the problem persists.
I am using an IDE for coding and Apache Tomcat ver.5.0.28 for the GUI part.

Anyone any idea why this is happening?
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