Effectively handling telephone calls about nursing home (NH) residents is an important skill for healthcare professionals, but little formal training is typically provided. The objective of the current study was to describe and evaluate the effectiveness of a novel structured role-playing didactic session followed by an on-call NH longitudinal clinical experience. The effectiveness of the structured role-playing didactic session was compared in different learners, including geriatric medicine fellows (n = 10), family medicine residents and faculty (n = 14), nurse practitioner students (n = 31), and other learners (n = 7). The curriculum focused on common problems encountered while caring for NH residents during on-call periods. Learners rated themselves using an 18-item pre/post questionnaire including five attitude and 13 skills questions, using a 1-to-5 Likert scale. T-tests were used to compare means before and after sessions. Significant improvements were found in overall mean attitudes and skills scores. For all learners, the greatest improvements were seen in “comfort in managing residents at the NH,” “managing feeding or gastrostomy tube dislodgement,” “identifying different availability of medications, laboratory studies, and procedures in NH,” and “describing steps to send NH residents to the emergency department.” Geriatric medicine fellows' attitudes and skills improved significantly after the longitudinal clinical experience. The faculty survey demonstrated improved documentation, communication, and fellows' management of on-call problems after curriculum implementation. This novel curriculum used role-playing to provide training for on-call management of NH residents. This curriculum has been successfully disseminated on a national geriatrics educational resource website (POGOe) and is applicable to geriatric medicine fellowships, internal medicine and family medicine residency programs, and other training programs.