There is an overall lack of training in the communication skills needed by physicians to effectively navigate challenging patient encounters. So-called difficult patients have specific obstructive behaviors that make it challenging to establish a successful doctor-patient partnership and can elicit strong negative emotions in the physician. Instead of labeling the patient as difficult, it is more useful to consider encounters as difficult events and rely on diagnostic and interventional techniques similar to those used in solving any other clinical problem. In difficult interactions, patients may have the perception that the physician is less technically skilled, they were allotted inadequate time, received poor explanations, and were overall dissatisfied with the visit. Physicians who experience difficult encounters may find it difficult to communicate with patients. The physician is often not attuned to the psychosocial aspects of patient care and is frustrated and uneasy with patients. To improve patient and physician satisfaction and healthcare outcomes, it is helpful to review the skills and strategies for delivering bad news, managing angry patients, addressing financial concerns, and dealing with drug-seeking patients.