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That is because your web application has a memory leak.
A common issue are "PermGen" memory leaks. They happen because Because the Classloader (and the Class objects it loaded) cannot be recycled unless some requirements are met (*). They are stored in the permanent heap generation by the JVM, and when you redeploy a new class loader is created, which loads another copy of all these classes. This can cause OufOfMemoryErrors
eventually.
(*) The requirement is that all classes loaded by this classloader should be able to be gc'ed at the same time.
Starting with Tomcat 6.0.25 there is a tool in the Manager webapp to help diagnose such misbehaving applications. See FAQ/Memory and MemoryLeakProtection.
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