When the path of the docBase of an application contains a symbolic link Tomcat still consider the initial targeted folder after a reload. Ex: when file system first contains: /foo/myApp_version1 (dir) /foo/myApp -> /foo/myApp_version1 (symbolic link) Tomcat is started and then application myApp is stopped. Symbolic link is changed to point to myApp_version2: /foo/myApp_version1 (dir) /foo/myApp_version2 (dir) /foo/myApp -> /foo/myApp_version2 (symbolic link) and finally application myApp is started. The problem is that the displayed web application is still the one contained in /foo/myApp_version1 (the initially targeted folder)and not the one contained in /foo/myApp_version2.
This behaviour is by design. You need to undeploy and redeploy your application for the changes to take effect. I have updated the docs in SVN to make this clear. The updated documentation will in included in 5.5.21 onwards.