History teaching in secondary school is intended to be a source of knowledge, hastening the nation-building process and enhancing the critical thinking and analytical skills of youth. It can serve as a tool for promoting peace and social cohesion within a nation. However, in Ethiopia, it has become a source of controversy, suspicion, hostility, and disharmony. This study investigates why history teaching in Ethiopia has not achieved its intended results, specifically its failure to prepare secondary school students to be critical thinkers and interpret the significance of the past. The study utilizes descriptive and historical research designs to explore this issue. Data were collected from primary and secondary sources, and the researchers employed the document analysis method to analyze them thematically and chronologically. The finding reveals that two main sets of 'conundrums', both external and internal, have prevented history from playing its desired role. These factors are interdependent: the internal issues stem from the external ones, and the external ones create fertile ground for the internal ones. Externally, factors such as foreign influences, foreign authors, and teachers played a role. Internally, factors like curriculum-based factors, disciplinary issues, ethnocentrism, the existence of competing narratives, and the state ideology of various regimes have impacted the direction of history teaching. Therefore, the combined influence of these internal and external dynamics has generally hindered the secondary school history teaching of the country from fulfilling its intended roles.