Errors in telephone communication can result in outcomes ranging from inconvenience and anxiety to serious compromises in patient safety. Although 25% of interactions between physicians and patients take place on the telephone, little has been written about telephone communication and medical mishaps. Similarly, training in telephone medicine skills is limited; only 6% of residency programs teach any aspect of telephone medicine. Increasing familiarity with common telephone challenges with patients may help physicians decrease the likelihood of negative outcomes. We use case vignettes to highlight communication errors in common telephone scenarios. These scenarios include giving sensitive test results, requests for narcotics, managing ill patients who are not sick enough for the emergency room, dealing with late-night calls, communicating with unintelligible patients, and handling calls from family members. We provide management strategies to minimize the occurrence of these errors.