The stratosphere is under rising pressure from two converging forces — climate influences and the rapid expansion of human activity in near-space. Satellite deposition and rocket traffic are introducing novel pollutants, with uncertain impacts on the ozone layer and broader environment, while mega-constellation plans accelerate. Emerging efforts to disperse material into the stratosphere to reflect sunlight, among the fastest-acting climate responses, raise new questions about environmental safety and new imperatives for governance. Navigating these challenges depends on our ability to monitor and characterize stratospheric conditions. Yet the world's advanced capabilities for measuring the stratosphere are sparse, aging and financially insecure. Just as the stakes rise, the data available to us could go dark. Featuring highlights of a new NOAA SABRE aircraft campaign and proposed STRIVE satellite mission, with the backdrop of the New York skyline, this dialogue will explore where we stand, critical gaps, and what can and should come next.