Using Bourdieu's theoretical model as a lens for analysis, we sought to understand how students experience the undergraduate medical education (UME) milieu, focusing on how they navigate transitions from the preclinical phase, to the major clinical year (MCY), and to the preparation for residency phase. Twenty-two medical students participated in this longitudinal case study. Students had similar preclinical and post-MCY experiences but different MCY experiences (rotational vs. longitudinal tracks). We interviewed students every 6 months in the preclinical phase, mid-way through MCY, and 7-8 months before graduation (101 total interviews). We inductively created codes, iteratively revised codes to best-fit the data, and thematically clustered codes into Bourdieu-informed categories: "field" (social structures), "capital" (resources) and "habitus" (dispositions). We found that students acclimated to shifts in the UME field as they moved through medical school: from medical school itself to the health system and back. To successfully navigate transitions, students learned to secure capital as medical knowledge and social connections in the preclinical and preparation for residency phases, and as reputable patient care and being noticed in the clinical phase. To obtain capital, and be well-positioned for the next phase of training, students consistently relied on dispositions of initiative and flexibility. In summary, students experience the complex context of medical school through a series of transitions. Efforts to improve UME would be well-served by greater awareness of the social structures (field) that students encounter, the resources to which they afford value (capital), and the dispositions which aid acquisition of these resources (habitus).