Background: Telehealth methods, including video chat counseling, have been growing in popularity within the behavioral health counseling field for over a decade. While video-based counseling methods have been shown to be effective and convenient, they have unique challenges stemming from the technology they use. Technical challenges can negatively impact appointment flow, intervention effectiveness, and the satisfaction of both patients and clinicians. Methodology: The Y2TEC (Youth to Text or Telehealth for Engagement in HIV Care) study is a pilot randomized control trial examining the feasibility and acceptability of a video counseling series provided to young adults (ages 18-29) living with HIV. The study's clinicians provided about 500 video-based counseling sessions through the Zoom videoconferencing platform. The study team then developed recommendations for overcoming technical challenges through a review of the best practice literature, insights from the clinicians and study coordinator, engaging in consultations during supervision meetings, receiving verbal feedback from participants, and reviewing logs of technical challenges. Results: Through our experience, we have found that quality of video-based counseling services can be greatly improved with minor intentional technological modifications in preparation and provision of services. We provide an overview of common challenges and corresponding recommendations to address them. Conclusion: This article can help clinicians improve their quality of telehealth sessions by identifying several common technological challenges that can occur during video chat sessions, exploring the impact of these challenges on session dynamics and providing concise, best practice-based recommendations to mitigate these issues that clinicians face.