Friendships between students with and without intellectual and developmental disabilities (IDD) remain infrequent, especially at the secondary level. However, when friendships between students with and without IDD have developed, direct support from parents and teachers has been a critical facilitator. Thus, this qualitative study examined parent (n = 10) and teacher (n = 20) perspectives on friendships and social interactions of middle and high school students with IDD receiving special education services in inclusive settings at least part of the day. The data were collected through semi-structured interviews with each participant and analyzed inductively using a multistage process of open and then thematic coding. The thematic findings suggest that the challenge of friendship development between students with and without IDD is ongoing, though there may be potential in focusing more explicitly and intentionally on increasing social interaction opportunities both in and out of school. Implications for future research and practice are described in the context of supporting students with and without IDD to increase social interactions and develop friendships.