Background: Mentors guide students in their challenges at school and in life. At-risk students in last-resort programs who are at a high risk of leaving school unqualified are especially in need of highly competent and adaptive mentors. This study therefore aimed to identify mentor qualities as perceived by at-risk students and their mentors that meet students' needs and mentors' capabilities. Methods: Face-to-face individual semi-structured interviews were conducted with students and mentors of two specialized programs in the Netherlands. Sensitizing concepts, derived from literature, were used to identify themes. Data analysis was conducted using thematic analyses and was validated by performing an audit. Results: The mentor qualities that at-risk students and their mentors reported were classified in three different themes. Mentor tasks consisted of guiding and motivating students and providing them with tangible methods of support. Relationships between mentor and student were based on levels of respect, equality, and bonding. Characteristics of mentors related to empathy, care, and trust. Research implications: Emotional responsiveness deserves further exploration as it appears to be an underlying concept of being a good mentor. Future research might explore mentor qualities in the context of other last-resort programs for at-risk students. Practical implications: Findings implicate that mentors have to walk a tightrope between keeping professional distance and being sensitive, suggesting constant attention to their professional development is needed. Originality: In the context of last-resort programs, an alternative perspective on mentoring at-risk students is outlined, based on perceptions of both students and mentors.