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There is a thread here http://old.nabble.com/Tomcat6.0.16-is-too-easily-to-be-OutOfMemory-compared-with-Tomcat5.5-td16921744.html

added 1 virtual user per 10 secs.
Only 30 virtual users, OutOfMemory was occured at Tomcat6.0.16,
but Tomcat 5.5.26 was 270 virtual users! 

So is it risky to upgrade from Tomcat 5 to Tomcat 6 as It doesn't seem obvious to configure Tomcat 6 to get the same performance as Tomcat 5 ?

In fact in the thread above nobody was capable of knowing the solution.

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We haven't seen this in our Tomcat 6 setup. That sounds pretty dramatic -- I suspect you have something else going on.

As of Tomcat 6.0.25, there's actually some quite nice capabilities for detecting memory leaks (particularly useful for OOME in regards to the PermGen memory).

http://wiki.apache.org/tomcat/MemoryLeakProtection

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