We present mechanical sympathy as a generative design concept for cultivating somaesthetic relationships with machines and machine-like systems. We identify the qualities of mechanical sympathy using the design case of How to Train your Drone (HTTYD), a unique human-drone research product designed to explore the process by which people discover and co-create the somaesthetic potential of drones. We articulate the qualities – (i) machine-agency, (ii) oscillations, and (iii) aesthetic pursuits – by using descriptive and reflective accounts of our design strategies and of our co-creators engaging with the system. We also discuss how each quality can extend soma design research; conceptualizing of appreciative, temporal, and idiosyncratic relationships with machines that can complement technical learning and enrich human-machine interaction. Finally, we ground our concept in a similar selection of works from across the HCI community.