Optimizing operations on critical infrastructure networks is key to reducing the impact of disruptive events. In this paper, we explore the potential of having humans and algorithms work together to address this difficult task. For this purpose, we use a gamified experiment to build and assess this potential in the context of the debris collection problem (i.e., “gamesploring”). We developed a digital game where players can request the help of the computer while facing a multi-objective problem of assigning contractors to road segments for clearing debris in a disaster area. Through a within-subjects experimental study, we assessed how players optimized under various circumstances (e.g., initial solution vs. from scratch) compared to the computer on its own. The results are both surprising as well as insightful: they suggest that human-machine collaboration is indeed beneficial but also that more work is needed on how to appropriately guide this form of collaboration.