In the Too Smart City section of the exhibition The Sentient City which takes place in New York between September 17th and November 7th, a series of artworks explore potential technological failures of augmented objects. The artworks embed concerns related to the loss of control of human beings in favor of technology, in line with Rich Gold’s witty and humorous critical interrogation into augmented spaces and objects, How smart does your bed have to be, before you are afraid to go to sleep at night? The exhibited pieces of sentient urban furniture, such as technologically augmented trashcans which would throw back at you pieces of trash which don’t match its intended content, are meant to generate reflection about the transformations and effects of living in an intelligent urban environment. Augmented urban furniture, such as the sentient trashcan or the smart bench have the capacity to become agents capable to regulate public behavior and impose sanctions. Public behavior is already regulated through urban design, rationalist and functionalist modern architecture towards passivity, uniformity, non-intervention and observation to replaced the previous ritualized modes of interaction in public space. Should sentient technological applications in public space be used to further regulate public behavior or to foster creativity and influence individual consciousness and public behavior towards imaginative and playful practices?