Recent technological advances have witnessed the rapid encroachment of computing systems into our social spaces. Their acceptance in these social spaces by other occupants, however, might be mostly contingent on their social appropriateness. Notions of social appropriateness might seem vague but even people who don’t act on this commonsense knowledge, and accord to social norms, can sometimes find themselves ostracized from society. It is reflected in behavior that supports a sense of successful engagement and connection. Such behavior communicates a desire to be accepted and a willingness to engage, as opposed to inappropriateness that conveys indifference, rejection or even danger. As social actors, how can systems improve their interactions with us in order to better succeed at their tasks? Perhaps, more interestingly, how might they even improve our communications with each other? In this thesis we describe a framework to identify opportunities to design systems that can begin to act appropriately in social settings, which we call Considerate Systems. It includes a design process and guidelines, which allows an interaction to be viewed from the perspectives of the user, system and task. It also includes an architecture that guides the addition of productive social responses to interactive systems. We demonstrate the utility of this framework by exploring two types of scenarios that impact social interactions in contrasting ways. Remote interactions (such as on a conference call) suffer from an impinging of social cues that people rely on while communicating. On the other hand, situated multitasking interactions (such as texting while driving) can easily overwhelm users and detract from their performance. The framework is applied towards the design of autonomous agents tackling problems endemic to such scenarios. We evaluate their success with respect to specific scenario goals. We conclude by noting that while the challenges of instilling computing systems with a sense of appropriateness seem daunting, our productive use of systems can be enhanced with them.