I seek one year of support to write a monograph that will explore the implications of convergent evolution for the contingency and replicability of complex life, with a focus on the iterated evolution of robust image-forming sensory modalities and their connection to complex behavior, cognition and consciousness. In Part 1, I present a critical analysis of the radical contingency thesis (‘RCT’), connecting it to contemporary philosophical discussions over the status of biological laws. I then consider a major challenge to the RCT that appeals to the ubiquity of convergent evolution, which I criticize for failing to distinguish between parallelism and convergence—a distinction that I defend from recent objections and show to have significant implications for the contingency debate. This culminates in a partial defense of the RCT, but it also sets the stage for a major critique to follow. In Part 2, I argue that due to constraints of the physical laws, image-forming adaptations have been realized through a diverse but limited set of perceptual-evolutionary pathways, casting doubt on the RCT. In Part 3, I argue that image-forming adaptations are connected to the emergence of cognitive complexity, phenomenal consciousness, and more sophisticated forms of goal-directed behavior. This will lead to the conclusion that, if the emergence of complex multi-cellularity is common in the universe, then cognitively complex and sentient species are probably common as well. However, I conclude in Part 4 that despite convergence on metacognition and limited social learning, technological species are probably rare, due to the peculiar suite of contingencies that underwrite the evolution of cumulative cultural capacities. Relief from teaching/administrative duties will allow me to draft the entire monograph, which will advance a novel thesis and will be accessible to a broad readership. I will also produce two scholarly articles and organize one conference exploring the project themes.