According to the documentation this is by design, since the tomcat5.5
user does not have the necessary privileges to make the changes:

/usr/share/doc/tomcat5.5/README.Debian

 There is a webapp for basic web-based administration of Tomcat's webapps
  in the tomcat5.5-admin package. You need to add one of the users in
  /etc/tomcat5.5/tomcat-users.xml to the manager role and probably
  set a better password. The "Web Application Manager" can then be accessed
  at http://localhost:8180/manager/html.
  
 There's also a more sophisticated  administration webapp called "admin" in the
 same package but it can't make  permanent changes to the configuration since
 the tomcat5.5 user does not have permission to do this in the default 
configuration.

-- 
Creating a new context using the /admin interface does not commit changes.
https://bugs.launchpad.net/bugs/220871
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