Advancements in converged networks, technologies, and IP-based multimedia communications are pushing the boundaries of when, where, and how people are able to communicate. As a negative repercussion, the lack of automatic behavior adaptation in wireless communication services is resulting in decreased levels of privacy, safety, security, and overall quality. Such a repercussion can be rectified through the evolution of information technology towards more aware, proactive, reactive, and generally more intelligent mobile devices. The Session Initiation Protocol (SIP) plays a large role in the development and exploration of this idea. We describe a contextaware SIP-based multimedia communication prototype that aims to enable locations to enforce communication policies on mobile devices and allow mobile devices to automatically adapt and negotiate the attributes of a communication session with other communication devices 'on the fly', both pre-session and midsession. Through experimentation we strive to identify the feasibility of such a system and discuss the practical considerations involved.