Purpose of Review The purpose of this paper is to review key lessons when using telehealth within the context of mental health and homelessness. We examine technological and bandwidth issues the homeless population might face when getting telehealth services, discuss clinical process adaption needed for working remotely, and highlight the lessons learned when leveraging mental health services to homeless patients across telehealth platforms. Recent Findings Homelessness is associated with chronic, mental health disparities and access to mental health services is often less accessible among communities with unstable housing. Telehealth provides “OnDemand” treatment options while removing specific barriers found with in-person health care such as transportation, overwhelmed mental health facilities, i.e., appointment availability, and office hour limitations while reducing costs for both providers and patients. Summary We provide two case examples to demonstrate successful delivery of telemental health services to homeless patients and review lessons learned when leveraging care.