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The COVID-19 pandemic and ensuing social distancing requirements resulted in an abrupt transition in the provision of most mental healthcare to telehealth; yet it was, at first, unclear whether patients’ emotional expressions – of great import to the success of many psychodynamic therapies – could be facilitated using teletherapy. This article first presents a targeted literature review focused on emotional expressions in psychotherapy and implementing psychodynamic therapy over telehealth and then describes our clinical experience transitioning a psychodynamically-informed, evidence-based, and experiential group treatment for chronic pain, emotional awareness and expression therapy (EAET), to video telehealth at VA Greater Los Angeles Healthcare System. We discuss barriers we encountered in our implementation of EAET over video telehealth but also illustrate the ultimate success of the approach using verbatim excerpts from our therapeutic work, which aim to demonstrate the potential to facilitate powerful emotional expressions over video telehealth when conducting a psychodynamically-informed treatment. We examine the possible applications for video telehealth to maintain emotionally focused, psychodynamic psychotherapy administration and enhance its teaching and training. Although we describe limitations of our specific approach, ultimately, our experience supports the potential efficacy of experiential, emotion-focused psychodynamic therapies in a telehealth setting.