Leaving old JARs in the WEB-INF/lib directory would not be an issue - if those 
classes are not used then all the file is doing is taking up disk space.

Of course, that tactic fails if you do something like combine all of the 
classes in one.jar and two.jar into one-two.jar. Then you would have one.jar, 
two.jar and one-two.jar in WEB-INF/lib which is guaranteed to be a mess.

I imagine you could code up you own classloading to load the client's custom 
JAR file so that file could be located anywhere, but that seems like a lot of 
work and fairly error prone. Some kind of deployment strategy seems easier to 
me, even if it is that you supply your customers with a deployer (which could 
be a script file) that does what you mentioned.

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