This descriptive case study uses self-assessment tools to explore 26 prospective students’ preparedness regarding their knowledge and competencies for entering the first year of engineering programs at a large, research-intensive Canadian university. We aim to provide insight for developing the Brigde2Engg (B2E) Program to empower and support students in their transition to university. Applying Conley’s college readiness model as a theoretical framework, findings from this study reveal that most students appear confident about their knowledge and skill preparedness for the first-year engineering programs, including their critical thinking abilities, problem-solving skills, and understanding of engineering professions. However, they are less confident in physics and the use of engineering tools. Therefore, we suggest that, when they choose to participate in the bridging program, these students should focus mainly on the subject they deem inadequate. Results also show that an introduction to engineering tools is essential to familiarize students with the programming and spreadsheet software they will use throughout their university programs.