I currently do consulting for a small business that has multiple applications that they need to login too.

I'm trying to get them to start using Basecamp and Zendesk to make all of our lives easier when it comes to collaboration on big projects and quick helpdesk ticket items.

However, I have recently been informed that it is difficult for them to remember all of these websites etc... to login too. However the login information is the same.

Right now they have to login to:

Windows Login Gmail

I want them additionally to login to Basecamp Zendesk

This is just a generation or two gap between myself and them, so I'm wondering what others do to solve these problems.

Is there some way we could configure USB thumbdrives that somehow have Lastpass or something on that when plugged into the computer automatically log them into their Windows account, then when they were to say visit the Basecamp account would automatically log them into that?

I think the security risk (of a list thumbdrive) is well worth the ability to use these extra applications.

Unless anyone else has any other ways for making it easier for users to login to multiple sites.