Mentoring is a common element of new teacher induction aimed at easing beginning teachers' entry into the profession and assisting beginning teacher growth and development. Previous research has shown that mentors are comfortable supporting beginning teachers but are reluctant to provide challenge-activities that will help beginning teachers improve their practice. For optimal growth to occur, mentors should balance support and challenge in their work with beginning teachers. This descriptive study employed multiple cases to examine the relationship of two junior high school mentors with their mentees. The mentors in this study work in a school district with an established and highly supportive mentoring program. Each mentor has received extensive preparation and ongoing support for their mentoring efforts. The purpose of this study was to examine how mentors balanced support and challenge in order to assist their mentees' growth. The relationships of two mentors, working with two beginning teachers each, were examined for elements of support and challenge as well as the ways in which the mentors and mentees positioned each other and were positioned. The mentors in this study strongly favored challenge over support in their interactions with their mentees. Although there were many similarities among the mentoring activities and conversations with the beginning teachers, each mentor had her own mentoring style and adapted their mentoring to meet the needs of the individual beginning teachers with whom she worked. One might expect challenge to be critical or negative, but the challenge found in this study was more nuanced and complex. The nurturing challenge found in this study was paired with support in such a way that the beginning teachers were not overwhelmed by the feedback they received. While the institutional expectations of mentors influenced how they positioned themselves in relation to the mentees, mentors also attempted to position mentees in a position of power within their own classrooms and with respect to their own development as beginning teachers. While at times both mentors and mentees resisted being in the position of dominance, for a majority of the interactions both parties accepted the institutional positions prescribed by the district program.