Is there something like a Virtual Reality documentary or is VR already leaving the realm of filmic representation? Where is the difference between a VR film and a VR experience, how can the 360-degree film be classified in this spectrum? Can both real-life VR and computer-generated projects be labelled as documentaries? Is non-fictional VR also allowing a kind of collaboration or cooperation as known from web documentaries, or are the projects finished works that exhaust themselves in the unique reception? Are VR projects used for exchange between human individuals or only for interaction between humans and machines (and their program flow)? The paper would like to pursue these fundamental questions, as they have not yet been fully clarified and repeatedly lead to irritation when dealing with individual examples. The method of the talk is an evaluation and comparison of publications from the field of VR studies, integrating information science (Gutierrez 2016), media psychology (Jerald 2015, Slater et al. 2019), and film studies (Tricart 2018, Dooley 2021). In doing so, three areas should be addressed: First, the style and design of the projects (computer-generated, real, hybrid), second, how the user is addressed and incorporated (as viewer, as interactant, as collaborator) and third, the question of experience should be clarified in connection to the further development of documentary film theory, also taking into account the role of new technologies and the possibility of collaboration between users. To this end, various approaches are called for and combined into a cohesive design. In the second step, different projects as examples are used to test the design, most of which come from the collection of DOK Leipzig, the documentary film festival in Germany, having a section called Neuland dealing with digital forms. The aim is to explore the limits of the theoretical and analytical definition with the practice of producing and curating projects. As a result of this discussion, an open matrix of possibilities with different levels of categorization will be proposed. The aim is not to find a fixed all-encompassing definition but rather to create a framework in which very different projects at the intersection of “reflection about the real world” and “use of a head-mounted display” can be integrated. One hypothesis is that such a multi-level, eclectic approach is more successful than just finding a large-scale definition that must be adapted individually for every project. This analytical matrix should serve for the further examination of examples on the different levels of design, address, and the emerging development of exploring reality via digital media concerning design and possibilities of collaboration. I want to discuss with others about this proposal to clarify the question of whether it is possible to define similarities and differences to deal with the works both in artistic and scientific discourses.