Critical approaches to smart technologies have emerged in HCI that question the conditions necessary for smart technologies to benefit people. Smart services rely on a relation of trust and sense of security between people and technology requiring a more expansive definition of security. Using established design methods, we worked with two residents' groups to critically explore and rethink smart services in the home and city. From our data analysis, we derive insights about perceptions and understandings of trust, privacy and security of smart devices, and identify how technological security needs to work in concert with social and relational forms of security for smart services to be effective. We conclude with an orientation for HCI that focuses on designing services for and with smart people and things.