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It looks like something "brakes" tomcat-users.xml during Mac OS X installation. If you take a look into $CATALINA_BASE/conf/tomcat-users.xml and $CATALINA_HOME/conf/tomcat-users.xml you can tell, that line endings are DOS like: 0000020: 662d 3827 3f3e 0d0a If you take a look at $CATALINA_BASE/conf/server.xml it has Mac OS ending while $CATALINA_HOME/conf/server.xml has DOS endings. The same refers to web.xml file