With advancement in modern technology, it is now possible for student teaching supervisors to virtually observe lessons remotely through the use of live video remote supervision. This innovation requires less overall funding (i.e., travel costs) and allows for highly qualified university professionals to provide direct feedback to student teachers. A phenomenological case-study approach was used to explore university supervisors’ perceptions and experiences with live remote supervision. Data from post-observation survey logs and a culminating focus group were collected from current physical education teacher education (PETE) program university supervisors (n = 3) from two separate higher education institutions. An interpretive phenomenological analysis (IPA) was conducted to best find meaning in the participants’ personal experiences. Qualitative results showed: (a) the iPad’s field of vision restricted the university supervisor from viewing all student teacher actions, though this was offset by increased ability to hear teacher through the Bluetooth, (b) initial and continual connectivity was problematic at times, (c) university supervisors rated the ability to hear every word the student teacher says to be very helpful (even more so than in live observations), (d) supervisors rated the quality of pre/post conferences and quality of observation to be high, though (e) this format did lose some of the personal touch of on-site visits. The findings suggest that remote supervision may prove to be a practical and cost-efficient way to facilitate supervision of field experiences in physical education and can potentially help shift towards a new paradigm of supervision in teacher education.