Introduction: In-service teacher training that explicitly addresses metacognitive and socio-emotional dimensions is essential for reimagining mathematics teaching in the 21st century. This multiple case study examines how a situated professional development program in mathematics education fosters reflective practice, emotional engagement, and didactic-mathematical competencies in two primary school teachers working in rural and semi-urban schools in Panama. Methods: Within the framework of the EDEM diploma program, based on the Didactic-Mathematical Knowledge and Competencies Model (DMKC) and the Onto-Semiotic Approach, we implemented a qualitative multiple case study design. Data included written responses to pedagogical tasks in four modules, reflective essays, video presentations of each teacher's final project, and institutional feedback. A deductive coding scheme based on the six dimensions of the DMKC (epistemic, cognitive, affective, interactive, mediational, and ecological) was combined with an inductive thematic analysis of metacognitive regulation (planning, monitoring, and evaluation) and socio-emotional practices (empathy, resilience, and classroom climate). Three researchers independently coded the corpus and achieved inter-rater reliability (Cohen's kappa > 0.85). The study received approval from institutional ethics committees and the Panamanian Ministry of Education. Results: Both teachers showed development in epistemic, cognitive, and affective dimensions, with more modest progress in the mediational and ecological dimensions. They increasingly articulated self-regulated teaching cycles by planning lessons aligned with learning objectives, monitoring student thinking, and evaluating their pedagogical decisions. Socio-emotional evidence indicated greater empathy, concern for students' emotional safety, and resilience in the face of infrastructural and curricular barriers. The cross-case analysis revealed distinct DMKC profiles: one teacher excelled in maintaining classroom dialogue and developing strong relationships with students, while the other showed more pronounced progress in the cognitive and mediational dimensions, particularly in lesson design and the strategic use of teaching resources. Discussion: These findings suggest that professional development experiences based on daily practice and theory can jointly strengthen metacognitive self-regulation and socio-emotional competence in mathematics teachers. This growth appears to strengthen teachers' sense of empowerment and emotional commitment to their work. The study illustrates how contextualized programs like EDEM can foster systematic reflection on teaching and offer an analytical and humanizing process through which teachers examine their decisions, emotions, and interactions to strengthen their professional capacity and improve student learning experiences.