In our qualitative study, we interviewed 45 Canadian teachers about mental health issues, taking a leave of absence, and their subsequent return to work. We found that doctors, supportive principals, supportive colleagues, supportive human resource departments, supportive school boards, and the teaching unions were facilitators for taking a leave, while stigma, unsupportive administration, preparation, and the process of taking a leave were barriers. In returning to work, principals and administrators, and preparation to return were cited as barriers, while colleagues, principals and administrators, doctors, unions and a change in work were facilitators. We interpret these findings through a synthesized framework combining Allegro and Veerman's theory of sickness absence and D'Amato and Zijsrtra's theory of work resumption, highlighting individual, organizational, and societal factors shaping leave and return decisions. With the high cost of teacher absences and critical staffing shortages, we discuss the impacts of these facilitators and barriers and make recommendations for practice for a healthy teaching workforce.