The simplest way to deploy a webapp to Tomcat is to create a WAR file and copy that file to the
TOMCAT_HOME/webapps/ folder. Tomcat will then (by default) unzip it to create a directory subtree with the same name as the WAR file, less the ".war" extension. The URL context assigned to the webapp will be the name of this directory, so if I drop
foo.war into
TOMCAT_HOME/webapps/, then the URL for the webapp would be
http://ipaddress:8080/foo/
You can use the Tomcat Manager webapp to upload the WAR into tomcat using its file-browse based deploy system, but the same effect will occur.
It's important to note that when you use
JEE container security you do NOT invoke the login page directly. The login page is automatically presented when the user is not logged in and has requested a secured URL from the webapp. If you attempt to access the login page via a direct client URL request, it won't work because the necessary security environment has not been set up.
The secret of how to be miserable is to constantly expect things are going to happen the way that they are "supposed" to happen.
You can have faith, which carries the understanding that you may be disappointed. Then there's being a willfully-blind idiot, which virtually guarantees it.