Telemedicine applications on a medical practitioner's mobile device should be context-aware. This can vastly improve the effectiveness of mobile applications and is a step towards realising the vision of a ubiquitous telemedicine environment. The nomadic nature of a medical practitioner emphasises location, activity and time as key context-aware elements. An intelligent middleware is needed to effectively interpret and exploit these contextual elements. This paper proposes an agent-based architectural solution called Context-Aware Mobile Medical Devices (CAMMD). This framework can proactively communicate patient records to a portable device based upon the active context of its medical practitioner. An expert system is utilised to cross-reference the context-aware data of location and time against a practitioner's work schedule. This proactive distribution of medical data enhances the usability and portability of mobile medical devices. The proposed methodology alleviates constraints on memory storage and enhances user interaction with the handheld device. The framework also improves utilisation of network bandwidth resources. An experimental prototype is presented highlighting the potential of this approach.