Drawing on employment records, qualitative interviews, and a survey, we explore the experiences of apprentices in the highway trades in Oregon. We demonstrate that female and racial/ethnic minority apprentices have lower rates of recruitment and retention and disproportionately face challenges with interpersonal interactions, hiring practices, and supervisory practices. Yet, we find a pervasive narrative that attributes apprentices' success to “hard work,” which contributes to the legitimacy of these inequalities. Consistent with the conceptualization of work organizations as inequality regimes, we argue that the apprenticeship system has policies, practices, and ideologies that are on the surface gender and race/ethnicity neutral, yet lead to the perpetuation of inequalities.