Many current HCI, social networking, ubiquitous computing, and context aware designs, in order for the design to function, have access to, or collect, significant personal information about the user. This raises concerns about privacy and security, in both the research community and main-stream media. From a practical perspective, in the social world, secrecy and security form an ongoing accomplishment rather than something that is set up and left alone. We explore how design can support privacy as practical action, and investigate the notion of collective information-practice of privacy and security concerns of participants of a mobile, social software for ride sharing. This paper contributes an understanding of HCI security and privacy tensions, discovered while “designing in use” using a Reflective, Agile, Iterative Design (RAID) method.