Pastoral peer mentoring often benefits both mentors and mentees through promoting a successful academic postsecondary transition. Based on interviews and focus groups with 36 York University mentors and mentees, this qualitative study highlights the successes and challenges of university pastoral peer mentoring and leadership. Major findings suggest that successful mentoring should focus on student-centered social and academic development, which includes supporting critical academic skills. Key components are collaboration and networking; helping students adjust to various academic, social, and bureaucratic aspects of university life; as well as encouraging retention. The research points to the importance of peer mentor and mentee training. In particular, mentee preparation is critical for ensuring that the mentoring process is both engaging and meaningful. Throughout the article, we identify the social, academic, and developmental outcomes that are necessary for positive results in pastoral peer mentoring of re-admitted students.