This study explores digital divide issues that influenced online learning activities during the COVID-19 lockdown in five developing countries in South Asia. A multi-layered and interpretive analytical lens guided by three interrelated perspectives—structure, cultural practices, and agency—revealed various nuanced aspects across location-based (i.e., rural vs. urban) and across gendered (i.e., male vs. female) student groups. A key message that emerged from our investigation was the subtle ways in which the digital divide is experienced, specifically by female students and by students from rural backgrounds. Female students face more structural and cultural impositions than male students, which restricts them from fully availing digital learning opportunities. Rich empirical evidence shows these impositions are further exacerbated at times of crisis, leading to a lack of learning (agency) for women. This research has provided a gendered and regional outlook on digital discriminations and other inequalities that came to the forefront during the COVID-19 lockdown. This study is especially relevant as online learning is being touted as the next step in digitization; therefore, it can inform educational policymaking and help build inclusive digital societies and bridge current gender and regional divisions.