Through several prototypes of a roof aperture for passive cooling in a desert climate, the relationships between design, thermal performance, and measurement are explored. Optimization of both day and night cooling modes within the same device requires the kinetic transformation of the aperture from a narrow downdraft chimney into an open radiation apparatus. Different methods are examined, from premeasured geometric optimization with constrained motion to a generalized design that can acquire numerous configurations and deploy algorithmic controls with live sensing to measure optimized performance during operation. The results are evaluated based on the structural-mechanical operation of the prototypes as well as the cooling effect they produce. Future steps and the implications for open-ended feedback-based design approaches are discussed.