Why will tomcat not serve newly created files?

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After updating a webapp I noticed that tomcat (5.5.23) won't serve any newly uploaded/created files even though the application creates and stores them. On trying to view the files I get a 404 error with the correct path name to the file listed. I however can browse to the file and open it. I redployed the app and then noticed that it serves an older version but I have no idea where the version it is serving is located and I have searched. It's like it's cached the version somewhere invisible and will only serve that version, like the context root is being changed to somewhere else. I am completely stumped as to why this is.

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The reason for the occurrence of the problem was not identified but the solution is here.

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developer On

Could be the erroneous attempt to replace a system file of code that is not overwritable, or the file cannot be accessed during your development session only after it is ended, or the environment has accepted your files and it may not have written them to disk at the server yet and updated the filestore or catalog, or there is a misspell of the filename.