Student teaching is a powerful formative experience for special education teacher candidates. Crucial to candidate success in student teaching is the effectiveness of their mentor teacher. However, the role of mentor teacher does not occur in a vacuum and context factors into the quality of the experience. A growing body of research indicates that a placement school's working conditions may also contribute to candidate outcomes. Yet, prior research provides little insight into how these elements may interact and relate to candidates' development. This study investigates this potential relationship and the ways in which they may shape candidate development. Results suggest mentor teachers' available planning time and collaborative relationships with general education colleagues are important working conditions in supporting relationships between mentors and candidates, candidate development, and candidates' future career plans. Implications and future directions for mentorship research are discussed.