Reflection is an educative form that encourages thinking and self-analysis, promotes an inquiry-based process, and enables problem-solving. This article focuses on the influence of students' tacit cultural assumptions and understandings in reflection learning. This study developed a context-tailored intervention to guide students' reflection competence development. The development of context-guided framework was supported by different learning models based on the literature. To examine the extent to which context-guided reflection influenced students to critically reflect and addressing tacit context assumptions during their transformative learning, this study used action research approach. The main research question that guided this study was: What is the impact of a tailored context-guided reflection model in students' transformative learning? In addition, this study also used three subquestions that derived from the main question: (1) What are the main characteristics of students' initial reflections?; (2) To what extent have the context-guided reflections influenced students to critically reflect?; and (3) How can context-guided reflection challenge tacit cultural assumptions in students' reflection learning? The study was conducted with a total of 288 reflective writings of Master students enrolled in the 2-year school counseling Master program of the Faculty of Education at the University of Prishtina in Kosovo, during 2017-2018 and 2018-2019 academic years. The results show that, largely, context-guided reflection improved students' reflective writings. The relevance of teaching and learning reflection based on contextual variables (tacit cultural assumptions, context-guided reflection, and program culture) is imperative to improve the quality of education professionals' transformation.