Telehealth-based care models are being widely adopted by primary care providers and large healthcare institutions. Drawing on data collected at an international conference on the theory and practice of telechaplaincy, this article identifies and discusses how chaplains navigate various telechaplaincy-related challenges. A thematic analysis identified 49 codes and 11 themes at the individual-, organizational- and population levels. Presenters reported facing novel and qualitatively distinct challenges spanning an array of telechaplains’ professional activities, including the structure of work routines, the types of interventions used, the ways provider-patient connections are established and experienced, the strategic positioning of chaplains, their role in the model of care, and ultimately, the populations served. It is argued that, though telechaplaincy has gained prominence since the Covid-19 pandemic, the maintenance of professional standards in digital care settings is a systemic challenge related to long-term trends towards outpatient care.