Privacy invasion, surveillance and profiling are some identified vulnerabilities as a consequence of trusting context-aware technologies such as smart-phones. With PC-enabled e-commerce transactions, the technological ecosystem was smaller with a corresponding simpler chain of trust. Context-aware technologies such as smart-phones are increasingly being used in initiating and completing commercial transactions. It is argued that newer and richer understanding of the issue of trust informed by mobile commerce is important. Research is needed to understand the nature of trust in context-aware technologies. This might lead on the one hand to valuable insights into the effect of the awareness of risks on user behavior and on the other hand, to suggestions on what can or should be done from the retailer or provider’s side to enhance the communication of risks and privacy issues to users.