In this review, we consider the insight that has been gained through theoretical examination of environmental sex determination (ESD) and thermolability - how theory has progressed our understanding of the ecological and evolutionary dynamics associated with ESD, the transitional pathways between different modes of sex determination, and the underlying mechanisms. Following decades of theory on the adaptive benefits of ESD, several hypotheses seem promising. These hypotheses focus on the importance of differential fitness (sex-specific effects of temperature on fitness) in generating selection for ESD, but highlight alternative ways differential fitness arises: seasonal impacts on growth, sex-specific ages of maturation, and sex-biased dispersal. ESD has the potential to generate biased sex ratios quite easily, leading to complex feedbacks between the ecology and evolution of ESD. Frequency-dependent selection on sex acts on ESD-related traits, driving local adaptation or plasticity to restore equilibrium sex ratio. However, migration and overlapping generations ("mixing") diminish local adaptation and leave each cohort/population with the potential for biased sex ratios. Incorporating mechanism into ecology and evolution models reveals similarities between different sex-determining systems. Dosage and gene regulatory network models of sexual development are beginning to shed light on how temperature sensitivity and thresholds may arise. The unavoidable temperature sensitivity in sex-determining systems inherent to these models suggests that evolutionary transitions between genotypic sex determination (GSD) and temperature-dependent sex determination, and between different forms of GSD, are simple and elegant. Theoretical models are often best-served by considering a single piece of a puzzle; however, there is much to gain from reflecting on all of the pieces together in one integrative picture.