Over the ages, higher education has been a vehicle for societal change by prompting the development of new ideas and the exchange of knowledge that support personal growth. Online education in Canada, with roots in print-based teacher training for people living in rural areas in the late 1800s, continues to provide an alternative for those living in remote locations and other traditionally under-served individuals. Long before the pandemic caused higher educational institutions to move on-campus courses into the online environment, and make use of synchronous video conferencing tools, online education was a welcome option for many Canadians. However, the flexibility and ease of access afforded by working in digital educational environments was countered by challenges for students who felt isolated and unmotivated. In 2006, a university in Western Canada piloted a not-for-credit module focused on encouraging new students to develop supportive learning communities by deepening their connections to their peers and beginning to build trust. Since its launch in 2006, several programs in the university have adopted the module, and in 2014 to 2021, we conducted a qualitative investigation exploring the experiences of master’s students as they worked together prior to the start of their for-credit course work. After receiving Research Ethics Board approval, focus groups and surveys were used to gather data, and an inductive approach was taken during the data analysis. The findings were organized into three anticipated themes: what worked well, what could be improved, and what could be added, with several emergent themes associated with each anticipated theme. Building on these findings, the recommendations focused on making the module a required component of the program, including both synchronous and asynchronous communication tools, encouraging the development of safe spaces, and considering flexible options for students working in different time zones and those with family and work commitments. These recommendations inform the development of activities for new students to motivate them to connect meaningfully with their peers, thereby reducing feelings of isolation.