As one of the most prominent trends in higher education, the appeal of online learning has been highly influenced by its potential to expand global access to high-quality education. However, many studies have shown that online learning programs paradoxically exacerbate the exclusion of socioeconomically under-resourced and culturally minoritized learners while widening educational disparities. Some researchers have attributed the inability of online learning to reach its potential to the prevalence of design choices that create cultural barriers to accessing content for participants who do not identify with the "normative" construction of the learner. The barriers emphasized in these studies include linguistic and communication challenges faced by non-native English speakers, the utilization of pedagogical frameworks unfamiliar to minoritized learners, and the deployment of content knowledge that predominantly draws on examples they deem unrelatable. Researchers have referred to these barriers to explain Arab learners' inferior online learning completion metrics compared to their peers globally, with many Arab learners challenged by program designers' deficit assumptions concerning their lived experiences. However, despite the underwhelming completion rates among Arab learners, nations in the Arab region are making significant investments in online learning for their potential to "democratize education" and support youth employability. Through a year-long ethnographic case study of the course design process of Edraak, the largest online learning provider for Arab learners, this study examines the cultural responsiveness of Edraak's online learning design process by exploring how course designers navigate the tension between designing culturally responsive online learning programs for all Arab learners and the multicultural diversity of "Arab" learners' lived experiences and aspirations. It also investigates how Edraak's learning community of learners, instructors, and program designers perceive the effectiveness of Edraak's culturally responsive design model in advancing their learning and engagement. Drawing on ethnographic observations, in-depth interviews with different learning community members, and Computer-Mediated discourse analysis (CMDA) of online engagement, this study shows the complexity of designing cross-cultural learning programs while navigating the tension between the assemblages of socioeconomic, cultural, and political factors influencing online learning design. The study uncovers the perennial tensions over the purpose of online learning and its affordances for advancing equitable learning and how these tensions manifest themselves and are perceived by the different learning community members. The dissertation concludes with recommendations for how online learning providers can design cross-cultural programs that help advance equitable learning and engagement.