Phenomenon: Communication is a complex and essential element of clinical practice. It is widely accepted that communication skills can be taught and learned, but challenges remain for clinicians in achieving effective communication with patients. This study explored the patient-communication challenges faced by both medical students and experienced clinicians. Approach: Semi-structured interviews were conducted with twenty medical students and nineteen experienced clinicians from a range of medical disciplines. Interviews were recorded and transcribed, and transcriptions subjected to thematic analysis and coding to quantify the challenges discussed. Findings: There was remarkable consistency in the challenges described by both groups of participants, with eight predominant challenges identified: time constraints and chaotic environments, rapport building, patient characteristics, reluctance, omissions, assumptions, decision-making, and keeping conversations focused. Insights: Medical curricula often focus on communication challenges associated with complex or sensitive clinical situations, but many of the challenges identified occur in routine consultations. Both pre-service and post-graduate medical training should adopt strategies to help build students’ and clinicians’ skills in managing these challenges from the outset of training.