The human experience is marked by constant learning. Moments of contention, when new experiences conflict with prior knowledge, often lead to the most meaningful learning. How do we successfully navigate these moments and gain new knowledge? In the current project, we aim to answer this question by characterizing (1) how individuals differ in their ability to learn in different situations and (2) the specific brain structures and pathways that guide new learning. We focus on the hippocampus, a brain region known to support memory and learning by connecting elements of experience across time and space. Here, we test the prediction that differences in individuals’ learning abilities arise due to differences of information pathways within the hippocampus. In other words, we predict that the flow of information through the hippocampus dictates how and what people learn from new experiences. We combine behavioural, brain imaging, and neural network modelling methods to investigate the structure of the hippocampus and how it supports the formation of rich knowledge in adults. Our multifaceted approach will provide novel insight into how the brain’s memory system supports learning and inform our understanding of disorders that impact learning (e.g., autism, schizophrenia).