Drones are currently an indispensable tool for emergency response teams performing wilderness Search And Rescue (SAR), as they can cover large and possibly inaccessible areas efficiently. It is, however, still unclear how a drone operator can effectively engage and control a system composed of multiple autonomous robots, especially in unstructured and outdoor environments. This paper reports on ongoing work in the project HERD—Human-AI Collaboration: Engaging and Controlling Swarms of Robots and Drones [6], in which we focus on how to enable an operator to control multi-drone systems. We present a tool for generating tasks and plans for multiple drones in wilderness SAR scenarios. The central aspect of our approach is to improve the search quality by automatically generating tasks to ensure timely coverage of high-risk areas, such as ditches, lake/sea banks, and beneath tree lines, where distressed people are likely to be found.