The proliferation of screens, satellites, and sensors presents new methodological challenges and possibilities for geography. This article provides a heuristic to guide empirical research that engages combinations of digital and material topics and tools. Analytically separating objects of analysis and methods of inquiry and locating them “on the ground” and “in the cloud” enables researchers to chart a pathway through complex digital geographies and research processes. Drawing on my own research in Myanmar farmers’ fields and Facebook groups, I demonstrate how iteratively combining in situ and digital ethnography, social media analysis, and interviews enabled me to understand agrarian and technological change, formulate new research questions, and adapt to acute constraints. As a strategy within growing methodologies for digital geography, moving from ground to cloud and back is a device for navigating empirical research that relies on an ethos of experimentation and an ethic of care.