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Mentoring practices occur predominantly “outside” the action of teaching (such as during debriefing sessions) and that mentoring “inside” the action (during classroom instruction) occurs less frequently (Schwille, 2008). This study explores how two mentors and eight new teachers’ in two high poverty urban schools experienced and perceived mentoring “inside” the action. Results indicate that mentoring predominantly occurred “outside” the action, and that mentoring “inside” was an underutilized practice. Furthermore, to maximize the potential of mentoring to improve instruction, new teachers and mentors may need to reconceptualize mentors’ time in the classroom from being an unobtrusive observer to a more active participant.