Objective: This study aims to examine the technical quality of videoconferencing used in hospice to engage caregivers as "virtual" members of interdisciplinary team meetings and their impressions of telehealth. Furthermore, it aims to compare the quality of plain old telephone service (POTS) and Web-based videoconferencing and provide recommendations for assessing video quality for telehealth group interactions. Materials and Methods: Data were obtained from an ongoing randomized clinical trial exploring Web-based videoconferencing and a completed prospective study of POTS-based videoconferencing in hospice. For the assessment of the technical quality, an observation form was used. Exit interviews with caregivers assessed impressions with the use of telehealth. A retrospective analysis of video-recorded team meetings was conducted rating attributes essential for the quality of videoconferencing (e.g., video artifacts, sharpness). Results: In total, 200 hospice team meetings were analyzed, including 114 video-recorded team meetings using Web-based videoconferencing and 86 meetings using POTS videophones. A direct comparison between the two modalities indicates the superiority of Web-based video in image quality but less so in audio quality. Transcripts of 19 caregiver interviews were analyzed. Caregivers found the use of videoconferencing to be a positive experience and a useful and essential tool to communicating with the hospice team. Conclusions: This study highlights the potential of telehealth to improve communication in hospice and the need for new tools that capture the quality of video-mediated communication among multiple stakeholders and strategies to improve the ongoing documentation of telehealth group sessions' technical quality.