I had a problem the other day where Tomcat would not redirect users to the HTTPS version of the login page (I am using the Spring Security plugin). It worked in development mode, but not in production.
The trick was to set both the grails.plugins.springsecurity.portMapper.httpPort
and grails.plugins.springsecurity.portMapper.httpsPort
properties to sensible values. Defaulting to 8080 and 8443 it makes sense they wouldn't work on prod. I found the answer via this Stack Overflow question