This case study investigated the process 119 faculty members underwent as they transitioned from using Desire to Learn (D2L) learning management system (LMS), to using Canvas LMS. Other than analyzing technological issues faculty members encountered while navigating various aspects of the Canvas interface, the study also analyzed technological issues faculty members come across while integrating software applications that work in Canvas. These applications included: Panopto, VoiceThread, Respondus Lockdown Browser, and Turnitin. The study presents implications to faculty members, instructional designers, and administrators.