Answers below :- 

(1) If you want to use JAAS for authentication, YES
(2) Passwords are NEVER stored in request. Principal can be got from the 
request after successful authentication by calling anonymous wrote : 
request.getPrincipal().
(3)After successful authentication Principal is cached till the expiry of 
HttpSession. Yes no, need for extra authentication till session expires.
(4) Can be used from JSP's and Servlets,. For that matter any web based client 
is fine this way.
Not Swing. You'll need to a typical JAAS login (with CallbackHandlers and 
config files) for that. No .NET client cannot do a JAAS login. 



Hope this helps


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