In this study, we describe participant characteristics, conversation content, and program success of an online mentoring program for northern Canadian youth. We investigate the associations between demographics and program success. The profiles and conversations of students and mentors that participated in the program between 2009 and 2013 were analyzed. Students were categorized into two groups (high and low engagement) based on the number of words written to their mentors. The high group contained proportionally more urban than rural students and equal proportions of Aboriginal and non-Aboriginal students, while the low group contained equal numbers of rural and urban students and proportionally more Aboriginal than non-Aboriginal students. This study provides valuable information on the use of online mentoring in northern communities.