I figured it out. I had to start
Tomcat in debugger mode. To do this I had to add a few parameters to catalina.bat:
set _EXECJAVA=%_RUNJAVA%
set MAINCLASS=org.apache.catalina.startup.Bootstrap
set ACTION=start
set SECURITY_POLICY_FILE=
set DEBUG_OPTS=-Xdebug -Xnoagent -Djava.compiler=NONE -Xrunjdwp:transport=dt_socket,server=y,suspend=n,address=5005
set JPDA=
Also, if you run Tomcat using the jar, it will not pick up these changes. You would have to start Tomcat using startup.bat.