This study examined students' attitudes toward distance learning, and its relationship with the duration of using Telegram and schooling. It specifically explored students' experiences of the challenges and opportunities that distance learning created during the COVID-19 pandemic. Accordingly, two null hypotheses were formulated: (1) there is no significant relationship between students' attitudes toward distance learning and the duration of using Telegram; and (2) there is no significant relationship between students' attitudes towards distance learning and the duration of schooling. Data were collected from a survey questionnaire and in-depth semi-structured interviews with students from the English Department of Herat University, Afghanistan. The quantitative data were analyzed using SPSS, an independent samples t-test, and ANOVA. The results of the t-test showed that the first hypothesis should be accepted, meaning there is no relationship between students' attitudes toward e-learning and years of Telegram use. Further, the one-way ANOVA test showed that the second null hypothesis was affirmed. Moreover, the qualitative findings indicated that distance learning via Telegram is associated with context-specific challenges and several opportunities.