This chapter critically analyses common challenges in Interprofessional Education and Collaborative Practice (IPECP) clinical supervision. Through a structured examination of theoretical foundations and empirical evidence, the chapter explores four fundamental challenges: resistance to feedback, balancing support with accountability, supervisory conflict, and burnout and stress. The analysis adopts a multilevel conceptual framework that recognizes the complex interplay between individual, interpersonal, professional, organizational, and systemic factors. Drawing on established frameworks including Proctor's Three-Function Model and the IPEC Core Competencies, the chapter examines each challenge through multiple lenses, considering contemporary manifestations, influencing factors, impacts on learning and practice, and evidence-based solutions. Additionally, the chapter addresses cross-cutting considerations including power dynamics, diversity and inclusion, technological transformation, and organizational contexts. By integrating research evidence with practical insights, this analysis provides actionable guidance for improving IPECP supervision effectiveness in preparing collaborative healthcare practitioners for complex, team-based care delivery.