First-generation and rural college students are considered by many retention theorists and practitioners to be an at-risk population. This study examined the details of the first semester in postsecondary education from the perspective of a group of students who met the demographic criteria of being first-generation to go to college, from rural geographical areas, and from agricultural backgrounds. It focused on the first semester experience, during its occurrence, and how six students of this specific population viewed that phenomenon. A secondary objective was to determine if the understandings that issued from the research could form a foundation from which first semester retention strategies for this particular population could be configured.