This article reports on a case study of Instant Messaging (IM) in a context of high-school virtual schooling. Data collection relied on interviews conducted with 20 participants in a context of high-school web-based instruction in Newfoundland and Labrador, Canada. The participants included e-teachers as well as other distance education personnel. Inductive analysis of the interview transcripts resulted in the identification of six categories of findings that we have labeled as follows: IM instructional affordances; IM comfort and preference; IM and classroom management; IM and social presence; IM and private versus public conversations; and IM and multitasking. The findings illustrate some of the challenges that can arise when a tool that typically serves solely a social purpose is appropriated into an educational context. Implications include the need for a knowledge base and professional development related to instructional strategies and techniques for managing IM and for capitalizing on the affordances offered by the tool. (Contains 2 figures and 1 table.)