The COVID-19 pandemic and the subsequent shift to online and hybrid learning brought to the forefront several long-standing issues within the educational domain, including engagement, collaboration, and motivation. During this period, many faculty members and students struggled to find viable solutions to these challenges. Previous studies have explored the use of Computer-Mediated Communication (CMC) to address these issues. In our study, we sought to develop a self-regulated CMC approach that would empower students to take charge of their own learning, engagement, motivation, and peer interaction. To do so, we created a self-regulated implementation to CMC using Slack. The implementation was introduced across four different courses at Pennsylvania State University. These were three undergraduate and one graduate-level course. Each course had its own Slack workspace with four separate channels, each created with its own purpose in mind, from asking questions to assignments and for general conversation. However, despite our initial assumptions, we discovered that adopting these channels fell short of our expectations as volunteers recruited from these courses did not use them beyond a few superficial interactions. To understand why our initial approach failed and to improve future iterations of self-regulated CMC, we conducted twelve 45-minute interviews with students from these four courses. The interviews helped us identify the main challenges that hindered the adoption of our approach, as well as the perceived motivational benefits. Based on these findings, we propose a gamified framework to increase engagement and adoption of self-regulated CMC in future implementations. Additionally, we suggest using emergent technologies for management and moderation to further enhance the efficacy of these approaches. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]