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I did a vanilla apt-get install tomcat on Debian Jessie. When I tried to start the service it failed (silently, even though it said it had succeeded). By doing research online and going through the logs, I was able to determine that tomcat was looking, during startup, in the "BASE" (/usr/share/tomcat7) for a variety of folders (example /server/classes) that exist in /var/lib/tomcat7.

By painstakingly creating manual links in /usr/shared, I was able to successfully get tomcat to start up and serve http requests. My question is, what's the right way to address this? There should be some intelligent way (i.e. smarter than what I'm doing) to configure this...

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If you only had read through Tomcat 7 Introduction, Directory and Files you'd know that this path is set in variable $CATALINA_HOME (as you only have one instance). Then, you wouldn't have bothered to create all these symlinks, but instead tried to find where it was set.

On a totally clean apt-get install the path, set in /etc/init.d/tomcat7 script, would have been correct. Possibly you had an old version e.g. from some previous try. There, you can find a line beginning with CATALINA_HOME= where the variable is set. Or simply --purge remove and install again to ensure you don't have old configuration files.

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