Future astronauts living and working on the Moon will face extreme environmental conditions impeding their operational safety and performance. While it has been suggested that Augmented Reality (AR) Head-Up Displays (HUDs) could potentially help mitigate some of these adversities, the applicability of AR in the unique lunar context remains underexplored. To address this limitation, we have produced an accurate representation of the lunar setting in virtual reality (VR) which then formed our testbed for the exploration of prospective operational scenarios with aerospace experts. Herein we present findings based on qualitative reflections made by the first 6 study participants. AR was found instrumental in several use cases, including the support of navigation and risk awareness. Major design challenges were likewise identified, including the importance of redundancy and contextual appropriateness. Drawing on these findings, we conclude by outlining directions for future research aimed at developing AR-based assistive solutions tailored to the lunar setting.