The successful teaching of communication skills (CS)—a key competency in medical education—depends on teachers’ expertise. Focusing on the experiences of CS teachers in Sweden, this study aims to explore the challenges they identify in teaching CS and how they adapt their practice accordingly. Individual interviews were conducted with 16 CS teachers, guided by a semi-structured interview guide. Data collection and analysis were iterative, aligning with constructivist Grounded Theory methodology. The teachers experienced a conflict between an idealized view of patient-centered communication taught during CS courses and the actual communication practiced in the clinical context, as well as students’ attitudes. This conflict permeated participants’ perceptions of their teaching goals, the challenges they faced, and the teaching strategies they employed. The teachers’ goals were to convey the purpose of CS, aiming for progress rather than expecting students to reach fixed goals and to promote student ownership in classroom practice. Challenges included students’ negative attitudes towards CS courses, their focus on succeeding rather than developing, and having to teach and examine simultaneously. Strategies focused on supporting learning by transforming negative attitudes towards CS teaching, providing a safe group climate, and offering constructive feedback to reduce defensiveness. This study highlights the need to bridge the gap between idealized CS teaching and clinical practice through institutional support, including curriculum integration, clear assessment frameworks, and recognition of emotional demands on CS teachers.