Many historically underrepresented students enroll in online classes because they need the flexibility to balance work, family, and coursework (Phirangee et al., 2016). However, community college students are less successful in online classes than they are in face-to-face classes (Xu & Jaggars, 2014). Feelings of isolation and disconnectedness are barriers to successfully completing online courses (Athens, 2018; Rovai, 2001; Shea & Bidjerano, 2010a). The purpose of this explanatory single case study was to understand the mediating role of experiencing a sense of community in asynchronous online courses for historically underserved college students at a minority-serving institution. The population for this study included five students and five instructors at a large minority-serving community college. Data were collected from semi structured interviews, research memos, and course syllabi, as well as written text from discussions and announcements in the learning management system (LMS). Findings showed that supportive and caring interactions in online classes create a safe space for students to be vulnerable, which promotes a sense of community in online learning environments for historically underrepresented students. Content analysis from discussion boards, as well as participant data, indicated that most participants find asynchronous discussions in the LMS to be inauthentic. The results also suggested that inclusive course design, e.g., incorporating multiple means of access and supportive teaching practices, plays a crucial role in supporting historically underrepresented students in online courses. Based on these results, the implications for practice are that faculty need to prioritize relational aspects when teaching online and promote academic interactions that foster a safe and caring asynchronous learning environment. [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.]