The most recent network technologies are enabling a variety of new applications, thanks to the provision of increased bandwidth and better management of Quality of Service. Nevertheless, telemedical services involving multimedia data are still lagging behind, due to the concern of the end users, that is, clinicians and also patients, about the low quality provided. Indeed, emerging network technologies should be appropriately exploited by designing the transmission strategy focusing on quality provision for end users. Stemming from this principle, we propose here a context-aware transmission strategy for medical video transmission over WiMAX systems. Context, in terms of regions of interest (ROI) in a specific session, is taken into account for the identification of multiple regions of interest, and compression/transmission strategies are tailored to such context information. We present a methodology based on H.264 medical video compression and Flexible Macroblock Ordering (FMO) for ROI identification. Two different unequal error protection methodologies, providing higher protection to the most diagnostically relevant data, are presented.