The use of telehealth technologies to provide clinical services to families of children with autism and other developmental disabilities is a rapidly growing area of research. In particular, remote training of caregivers via video conferencing appears to be a promising approach for disseminating behavior-analytic interventions (Neely et al. in "J Dev Phys Disabil" 29:849-874, 2017. 10.1007/s10882-017-9550-4; Tomlinson et al. in "J Behav Educ" 27:172-222, 2018. 10.1007/s10864-018-9292-0). Although remote training offers a number of advantages, it brings a variety of challenges that are unique to this modality. The field would benefit from information on problems that practitioners may encounter when providing these services and how to train caregivers effectively. In this paper, we report on the experiences of 18 practitioners who provided caregiver training via telehealth from four different sites across a 4-year period. We describe a variety of technical and clinical issues that arose during service delivery, suggest strategies for preventing and remediating problems, and include case descriptions and data to illustrate our experiences. This information may help prepare practitioners to deliver telehealth services and guide further research in this area.