This qualitative case study investigates challenges faced by educators teaching trigonometry in Grade 12 within the Alfred Nzo West Education District, where persistent underperformance is linked to socioeconomic and resource limitations. Using a constructivist paradigm, six educators from diverse backgrounds participated in semi-structured interviews. Key issues include reliance on traditional, less engaging methods, limited use of technology, and insufficient, sporadic professional development. Findings suggest that while traditional approaches provide structure, they often fail to foster deep student engagement, whereas technology, when accessible, enhances understanding. Professional development lacks specificity to address the unique challenges of trigonometry pedagogy. The study concludes by recommending increased teacher training, improved resource distribution, and greater technology integration to support teaching effectiveness. These changes could help address educational inequalities in the district, promoting better academic outcomes and learner advancement in trigonometry.