The goal of this study was to gain student-centered insights to better understand the challenges of transitioning from undergraduate to dental education. To this end, questionnaires were designed and distributed to incoming dental students, as well as second-, third-, and fourth-year students in the same year for a cross-sectional assessment in 2015/2016. The same questionnaires were also distributed to those same incoming students when they were in their second, third, and fourth years for a longitudinal assessment (2015-2019). There were both open-ended and Likert scale-type questions about expectations (incoming students) and experiences (years 2-4) in dental school compared to undergraduate education. Accordingly, data analysis involved a combination of qualitative and quantitative statistical approaches. Cross-sectional and longitudinal analyses showed that incoming students expected an increased workload in dental school, but also more attention, support, and access to faculty than they received as undergraduates (i.e., they expected a stronger academic support system). All students also reported experiencing more stress and greater difficulty managing their time than expected when compared to their undergraduate experiences. Thus, our study highlights areas of discrepancy between dental students' initial expectations and their lived experience. Importantly, dental schools can take measures to address these discrepancies, foster a better learning environment, and improve students' overall experience to help pave a smooth path for students to become successful and well-prepared oral health care providers.