Demonstrations that include virtual reality (VR) technologies are becoming increasingly common in research contexts. All included roles within a demonstration experience (facilitators, participants, and spectators) take up different responsibilities to be able to run through a VR demonstration as intended. VR head-mounted displays (HMDs) are particularly difficult to demonstrate with considering the participant’s restricted vision of their surroundings and the facilitator. There is limited HCI research that has analyzed interactions between the roles of a demonstrations when using VR HMDs. Therefore, this study explores how these roles address the challenges that arise during VR demonstrations. With a video-analytic approach, we gathered data from live demonstrations from an ACM conference in 2024. To articulate the data gathered, we encompass the concepts of breakdown and repair, alignment and common ground, and progressivity. Our findings highlight five forms of alignment work: procedural, technological, conversational, visual, and physical alignment, as well as preemptive repurposed conversational repair strategies. This paper’s main contribution is the forms of alignment that provide discourse tools for analyzing alignment work interactions and understanding them in the context of VR demonstrations. Additionally, this research provides actionable guidelines aiding VR-experience organizers as a way to limit breakdowns and arrested progressivity in their demonstrations, applicable in context from lab-based experiments to public exhibitions. These guidelines include to inform sequentiality, inform about differences in interactions and technologies, preempt physical surroundings, and negotiate touch. We conclude by encouraging future research to explore implications of designing for interactions and designing for specific demonstration roles.