In this article, we explore findings from a semester-long online mentoring project between graduate students enrolled in a doctoral program and university students observing in local high schools early in their teacher education program. The project's goals were to provide supervised mentoring experiences for doctoral students to better prepare them to mentor future preservice teachers and to provide teacher education students with support during their first school observations. We compare several groups' online discourse strategies and levels of social presence to show how the discourse positively or negatively affected communication between the two groups of students.