QGR visitor and friend Michel Planat (Senior Research Scientist, University of Franche-Comte, FEMTO-ST) posits the geometry of cosets in the subgroups of the two-generator free group nicely fits, via Grothendieck’s dessins d’enfants, the geometry of commutation for quantum observables. In previous work, it was established that dessins stabilize point-line geometries whose incidence structure reflects the commutation of (generalized) Pauli operators. Now we find that the nonexistence of a dessin for which the commutator precisely corresponds to the commutator of quantum observables on all lines of the geometry is a signature of quantum contextuality. This occurs first at index : in Mermin’s square and at index in Mermin’s pentagram, as expected. Commuting sets of -qubit observables with are found to be contextual as well as most generalized polygons. A geometrical contextuality measure is introduced.