The emergence of the COVID-19 pandemic brought into evidence some of the challenges of deploying and managing user studies out-of-the-lab. Satisfying new health guidelines required adapting to remote and contactless procedures, which in turn impacted recruitment, participant involvement, and technology delivery and configuration. Such challenges are endemic to many user studies. However, the emergence of the pandemic forced us to confront them head on in two distinct multidevice deployment studies. Changing research design, deployment strategies, and study management allowed us to reflect on some of the core challenges for all field related technological interventions and provided insight into how researchers might conduct more responsive, flexible, and robust studies outside the lab more broadly. Our reflections suggest simple but important ways that researchers can design flexibility, responsiveness, and empathy into all future user studies in- the-wild.