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The Problem with Single Sign-In Systems: "One of the more thankless jobs at MSN Windows Live is to work on the Passport team. Many of the product teams that are customers of the service tend to view it as a burden, myself included. One of the primary reasons for this is that instead of simply being the username/password service for MSN Windows Live it is actually a single-sign in system which encompasses a large number of sites besides those owned by Microsoft. For example, you can use the same username and password to access your email, travel plans or medical information. Trevin Chow of the Passport team has written a blog post entitled Why does Passport sign-in suck? where he addresses one of the pain points its customers face due to its legacy as a single sign-in system. He writes Q: Why do you keep asking me to sign in over and over again even though I've checked 'automatically sign me in'?  What don't you understand about 'automatic'?!   One of the biggest problems with see in the network of MSN, Windows Live and Microsoft sites is that Passport sign-in is seen way too often by users.  It appears as if we are disregarding your choice of 'automatically sign me in' and randomly asking you to sign in when we want with no rhyme or reason...   Passport sign-in 101 Passport sign in"