While the past century of neuroscientific research has brought considerable progress in defining the boundaries of the human cerebral cortex, there are cases in which the demarcation of one area from another remains fuzzy. Despite the existence of clearly demarcated areas, examples of gradual transitions between areas are known since early cytoarchitectonic studies. Since multi-modal anatomical approaches and functional connectivity studies brought renewed attention to the topic, a better understanding of the theoretical and methodological implications of fuzzy boundaries in brain science can be conceptually useful. This article provides a preliminary conceptual framework to understand this problem by applying philosophical theories of vagueness to three levels of neuroanatomical research. For the first two levels (cytoarchitectonics and fMRI studies), vagueness will be distinguished from other forms of uncertainty, such as imprecise measurement or ambiguous causal sources of activation. The article proceeds to discuss the implications of these levels for the anatomical study of connectivity between cortical areas. There, vagueness gets imported into connectivity studies since the network structure is dependent on the parcellation scheme and thresholds have to be used to delineate functional boundaries. Functional connectivity may introduce an additional form of vagueness, as it is an organizational principle of the brain. The article concludes by discussing what steps are appropriate to define areal boundaries more precisely.