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While online tutoring programs have shown promising results for students, many use strictly controlled content and lessons. A persistent problem in remote tutoring is how to promote meaningful engagement, effective learning activities, and strong tutor-tutee relationships. Through qualitative analysis of reflections completed by tutoring pairs (a tutor and a middle school student) as part of a remote University-school tutoring partnership, this research explores how tutoring pairs describe their relationship, how they perceive and engage with tutoring activities, and what insights and suggestions they have for improving tutoring. Participants expressed the importance of tutors responding to students’ requests for activities, that relationships were crucial to successful tutor/student relationships, and a preference for engaging, relevant activities.