The prevalent use of interactive whiteboards (IWBs) in K-12 classrooms has been met with questions regarding how teachers use such technologies to facilitate student learning. We analyzed recorded observations of 21 ELA middle school teachers over a single academic year as they developed knowledge about and competence with a structured reading programme, Collaborative Strategic Reading (CSR, Klingner, J. K., S. Vaughn, A. Boardman, and E. Swanson. 2012. Now we get it!: Boosting Comprehension with Collaborative Strategic Reading. Hoboken, NJ: John Wiley & Sons) while simultaneously learning IWB technologies. Findings suggest a) the importance of using explicit instructional prompts for facilitating student collaboration and b) the need for adequate time for teachers to gradually incorporate technology into classroom practices over the academic year.