Files in the work and temp directories depend on timestamps to be overwritten.
If you deployed the web app using WAR file originally, then you need to either redeploy the entire WAR file or need to meet any of the conditions listed in the official Apache Tomcat documentation.
Your other two options are:
If you are having trouble with files not updating in the work and temp directory it is possible you may have a conflict with timestamps. The work and temp directory are used for compiled jsp files, so if your compiled jsp files timestamp are newer than the timestamp of your new jsp files then Tomcat will only serve the old files. Therefore, you need to check and compare the timestamp of the newly deployed web app with the in the work or temp directories. If the files in either directory are newer, you’ll need to delete the old web app files in work directory or touch all the new web app files to update their timestamp.