Digital assessment has become central to Open Distance e-Learning (ODeL), yet its implementation often assumes equitable access to digital resources, potentially disadvantaging students studying in diverse geographical and socio-economic contexts. This study examined how students’ living contexts influence their experiences of digital assessment in undergraduate mathematics education at a South African distance education institution. An explanatory sequential mixed-methods design was employed. Survey data were collected from 253 undergraduate students, with 251 participants included in the inferential analyses after excluding two respondents who selected “Other” as their living area category. Quantitative data were analysed using chi-square tests, binary logistic regression, and ordinal logistic regression, while qualitative responses were analysed thematically. The findings revealed that living context was significantly associated with reliable internet access, and internet reliability significantly associated with students’ experiences of typing and submitting digital assessments as well as their perceptions of assessment inclusivity. Qualitative findings further highlighted challenges relating to connectivity, device limitations, mathematical representation, and the need for more flexible assessment practices. The study advances Contextualized Digital Assessment as a conceptual framework for designing equitable digital assessment that recognises students’ diverse technological, geographical, disciplinary, and socio-economic realities. The findings provide practical guidance for higher education institutions seeking to design more inclusive and context-sensitive digital assessment within ODeL environments.