For decades schools have struggled with how to teach and increase the learning of mathematics in children. It has been the focus of multiple federal programs and funding agency (NSF, NIH, IES, and Gates Foundation) initiatives. Even with all of this focus and research dollars, we see very few changes in children increasing their ability in mathematics especially in foundational skills like fractions. This presentation will review my research over the last few years on trying to understand the developmental pathways of math achievement. I will explore both individual characteristics (self-concept) and contextual influences (parenting, socioeconomic status) that may relate to the early development of math skills and the long-term outcomes related to these skills. Current issues involving the struggle with learning loss after the COVID-19 pandemic will also be highlighted.