This study seeks to extend wicked problems analysis within the context of a library’s support for virtual reality (VR) and the related extended reality (XR) emerging technologies. The researchers conducted 11 interviews with 13 librarians, embedded IT staff, and/or faculty members who were involved in administering, managing, or planning a virtual reality lab or classroom in a library (or similar unit) in a higher education setting. The qualitative analysis of the interviews identified clusters of challenges, which are categorized as either emergent (but solvable) such as portability and training; complicated (but possible) such as licensing and ethics: and/or wicked (but tameable). The respondents framed their role in supporting the wickedness of VR/XR in three basic ways: library as gateway, library as learning partner, and library as maker. Five taming strategies were suggested from this research to help librarians wrestle with these challenges of advocating for a vision of VR/XR on their respective campuses. This research also hints at a larger role for librarians in the research of technology diffusion and what that might mean to their role in higher education in the future.