Vending machines are often considered mere dispenser facilities that elicit only low engagement in their users. Instead, it is a market that is not only growing and expanding, but also evolving from a technological as well as service point of view. The City of the Future Living Lab in Milan has designed alongside its users an interactive Internet of Things vending machine based service which has been successfully deployed and is being tested in a public space within the Living Lab. This paper would like to present this as a case studies of designed experiences for behavior change.