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The purpose of this research full paper is to investigate issues facing very early-stage master’s students as they transition into a degree program at a large research-intensive university. While there is an increasing focus on graduate and doctoral engineering education, few studies have sought to focus specifically on master’s students, treating them from a research perspective as miniature doctoral students, though it is documented that MS students in engineering have different goals and motivations for pursuing graduate study than PhD students, as well as different anticipated career trajectories. To further compound these gaps in the literature, most studies assume that doctoral students in engineering come from historically privileged socioeconomic backgrounds. National conversations are clear that to broaden participation in engineering, the educational community must attend to the specific needs of students from low-income backgrounds. These students may also not have access to the social and cultural capital required to navigate graduate school, since many are first-generation graduate students and because systems of education are traditionally designed for students from upper class backgrounds. To this end, this study explores the experiences of first-semester graduate students supported in part by funding aimed to support master’s students and have demonstrated unmet financial need. Interviews were conducted with six first- and second year master’s students and analyzed using thematic analysis methods employing Posselt’s Framework for Doctoral Student Support—here, extended to master’s students—to elicit information about surprises, expectations, and unanticipated issues facing this special population of students. Findings indicate that there are several easily implemented structural modifications programs and faculty can take that can facilitate the transition to graduate school for graduate students, low-income and otherwise.