I cannot tell if you mistyped the file names (you mention both Login/.jsp and Login.jsp, which one is correct?) in your post, or if your mistyped you configuration (for example, the file is really named Login.jsp but you have indicated Login/.jsp in the web.xml).
In my application, my login JSP is called login.jsp, so there is no issue with using that name.
Perhaps you should post the security settings within your web.xml file.
yes it is Login.jsp it was a typo for the slash in the name, saw it after I posted it. well as weird as it sounds login.jsp (note the lower case L) works and Login.jsp (the cap letter one) does not.. the lower case one without any security setting works ok.. I did see some verbiage online that someone else ran into some problem similar to this because of some conflict with root context having something similar..not sure how they got around it.