This document discusses some of the difficult challenges in designing pervasive computing systems, including balancing proactivity and transparency, privacy and trust issues, and the impact on system layering. Specifically, it notes that balancing proactivity and transparency requires finding the proper level of transparency that does not annoy users. It also discusses the privacy challenges from systems that continuously monitor users and the need to establish trust between users and infrastructure while minimizing intrusiveness. Finally, it acknowledges the need for layering in systems but also the challenges this poses when more information sharing across layers is required for pervasive systems.