Maps are the culmination of numerous choices, with many offering multiple alternatives. Not all of these choices are inherently guided by default, clarity, or universally accepted best practices, guidelines, or recommendations. In the realm of cartography, it is a distinct feature that individual decisions can be made, particularly regarding data preparation and selection and design aspects. As each map is a product of a multitude of decisions, the confidence we place in maps hinges on the reasonableness of these decisions. The trustworthiness of maps depends on whether these decisions are sound, unquestioned, readily accessible, and supported by dependable groups of decision makers whose reliability can be assessed based on their track record as an institution, reputation, and competence. The advent of user-friendly map-making software and data manipulation tools has placed some of these decisions in the hands of the general populace and those interested in using maps to convey specific agendas. This mirrors other forms of communication and has given rise to a growing discourse on “fake news”, “fake media”, and “fake maps”, ultimately prompting us to question how we can trust the information being conveyed and how we can differentiate between “fake” and “trustworthy” maps. This paper highlights the fundamental aspects determined by the pure nature of cartographic modeling, which influences every attempt to understand, analyze, and express the context and trustworthiness of maps. It then identifies fundamental aspects of trustworthiness with respect to maps. Combining these two fundamental considerations represents an epistemological attempt to identify a research portfolio. An example of an empirical study on identifying selected aspects of this portfolio demonstrates the potential of gaining a better understanding of the context given.