The author describes how, during the COVID-19 pandemic, clinicians embraced telehealth for vulnerable children struggling with intense feelings, learning challenges, and isolation. She suggests that generating playful engagement, however difficult without the toys and comforts of the traditional office, remains crucial. She discusses the stresses of the telehealth experience and the importance of identifying and mobilizing a child's initiative and agency in this setting. She asserts that, when clinicians maintain empathy and share how they imagine children's experiences, a joining can occur that lessens the children's sense of isolation and emotional hurdles. She then concludes that, if a clinician's imaginative self becomes engaged with that of a child, spontaneity and forward movement are possible even when employing the medium of telehealth.