To date, minimal research has explored the perceptions of secondary school staff regarding their realized and potential contributions to the redress of mental health stigma and support of students with mental health concerns within school environments. The aim of this study was to identify and describe the practicable roles school staff perceive of themselves to hold with respect to promoting mental health, challenging stigma, and responding to student mental health problems. Using an interpretive qualitative approach, semi-structured interviews were conducted following purposive and convenience sampling of school staff (n = 48) including classroom teachers, school counsellors, psychologists, administrators, and various support staff members employed with two secondary schools in southern Alberta, Canada. A structured interview guide was utilized to assess the roles, tasks, and processes school staff undertake to assist students with their mental health concerns. Four main themes inductively emerged from the data: (1) "Relationships matter": Establishing and maintaining strong relationships with students, their caregivers, and other staff members are critical to addressing student mental health issues; (2) "Empathetic and receptive communication is an antidote to stigma": Various communication processes contribute to disclosures of mental health concerns and challenges; (3) "Connecting and facilitating timely access to the right person is key for students experiencing emotional crises"; and (4) "Facilitators and barriers to addressing student mental health concerns." Clinical implications and policy recommendations are provided to inform directions for administrators, educators, and caregivers regarding student mental health supports.