In the following position paper we introduce the use of AR HMD for remote instruction in healthcare and present the challenges our team has faced in achieving this application in two contexts: surgical telementoring and paramedic teleconsulting. After the presentation of how these challenges come to be and indications on how to address them, we argue that those who wish to pursue this area of research must be grounded in best practices from the field of CSCW integrated with technical innovations in AR interaction development. This is a truly interdisciplinary research and development area that has many challenging topics to tackle through collaborative efforts