This bug only occurs with with tomcat5.5_5.5.23-1 (lenny/sid), not with 5.5.20-2 (stable).
Maybe moving the configuration files from /var/lib/tomcat5.5/conf to /etc/tomcat5.5, or the switch from ${catalina.home} to ${catalina.base} causes this. Thanks for your report, I will look into it. Jan-Pascal