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The COVID-19 pandemic provides a real-world opportunity to explore the Winnicottian concepts of transitional objects and transitional phenomena in the context of online or distance treatment. The capacity for transitionality, delineated by Angela Joyce, may be an important element in determining a patient’s ability to use remote therapy. The case report of a young child’s pre-pandemic and interpandemic remote psychoanalytic treatment is used to illustrate the developing capacity of transitionality and possible technical interventions to promote its elaboration.