Contextuality can be understood as the impossibility to construct a globally consistent description of a model even if there is local agreement. In particular, quantum models present this property. We can describe contextuality with the fibration approach, where the scenario is represented as a simplicial complex, the fibers being the sets of outcomes, and contextuality as the non-existence of a global section in the measure fibration, allowing direct representation and formalization of the already used bundle diagrams. Using the generalization to continuous outcome fibers, we built the concept of measure fibration, showing the Fine-Abramsky-Brandenburger theorem for the fibration formalism in the case of non-finite fibers. By the Voroby'ev theorem, we argue that the dependence of contextual behavior of a model to the topology of the scenario is an open problem. We introduce a hierarchy of contextual behavior to explore it, following the construction of the simplicial complex. GHZ models show that quantum theory has all levels of the hierarchy, and we exemplify the dependence on higher homotopical groups by the tetraedron scenario, where non-trivial topology implies an increase of contextual behavior for this case. For the first level of the hierarchy, we construct the concept of connection through Markov operators for the measure bundle using the measure on fibers of contexts with two measurements and taking the case of equal fibers we can identify the outcome space as the basis of a vector space, that transform according to a group extracted from the connection. With this, it is possible to show that contextuality at the level of contexts with two measurements has a relationship with the non-triviality of the holonomy group in the frame bundle. We give examples and treat disturbing models through transition functions, generalizing the holonomy.