This study aims to measure the magnitude of the cultural factors that affect enrolment and retention in both primary and secondary education levels in Afghanistan and advocate cultural transformation or modification in Afghanistan to enhance enrolment and retention in school. The study uses quantitative and particularly qualitative data regarding cultural constraints to school enrolment and retention in Afghanistan from secondary sources like Afghan government publications, private publications, publications from non-government organizations, journal articles, newspaper articles, newsletter articles, web documents, dissertations, published interviews, database articles, and books. It employs Hofstede’s cultural dimensions model to analyze the cultural factors. However, the study found out that on the scale of Geert Hofstede’s cultural dimensions model, Afghan culture was characterized by high degree of power distance, masculinity, i.e., conventional gender role focus, high level of uncertainty avoidance, and long term orientation that were deterrents to education in Afghanistan. Finally, it recommends a culture with low level of power distance, femininity focus, low degree of uncertainty avoidance, and long term orientation to increase school enrolments and retention in Afghanistan.