I saw this just today. I did some digging and realized that my application context file, usually found under $ CATALNA_HOME/conf/Catalina/localhost was messed up. After I fixed whatever problem it was, I was able to deploy again.
Michal Kwiatek wrote:

Hello,

I have a problem with tomcat 5.5.9 - for some reason tomcat does not
recompile JSPs after I redeploy the application using manager
application.
There's no error message in the logs, tomcat has write access to work
directory and it compiles new jsps. It simply does not recompile the
existing ones.
Have you seen such behaviour in the past?

Thanks in advance,
Michal.

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