Clinical interactions demand a balance of structure and flexibility in response to unpredictable situations. Medical improv is a form of experiential learning that applies techniques from improvisational theater to the healthcare setting, deliberately targeting clinical skills of communication, teamwork, and cognitive abilities. Psychiatry Education through Play and Talk (PEP Talks) is a novel medical improv program designed specifically for psychiatry residents with the goal of improving communication, teamwork, and conflict resolution skills, as well as enhancing residents' well-being and capacity for self-reflection. PEP Talks was delivered virtually by an experienced medical improv facilitator in spring 2021 to a self-selected group of psychiatry residents at a Canadian university. Aligned with the context-input-process-product (CIPP) evaluation model, outcomes were assessed through mixed methods surveys, recorded debriefings, and a focus group. PEP Talks enhanced residents' self-reported well-being, reflective capacity, and communication skills. Participants made qualitative connections between PEP Talks and their well-being, inter- and intra-personal skills, and clinical experiences in psychiatry. Processes in PEP Talks that led to these outcomes included the following: joy, building community, personal reflection and discovery, going off-script, immersion, and virtual engagement. Virtual medical improv offers an innovative solution to the pedagogical challenges of training psychiatrists to be proficient communicators, collaborators, and professionals capable of reflective practice. Additionally, this innovation demonstrates that medical improv can be delivered in a virtual format and may offer a unique solution to support resident well-being and foster connection amid remote learning during a global pandemic.