The effect of tautomerism on the aromaticity was studied for the free base triazoleporphyrazine at the Density Functional Theory level, using double-zeta double polarized basis sets. The porphyrazine (1), the three tautomers (2a, 2b and 2c) as well as the Ni complex (3) of triazoleporphyrazine were examined. Two independent aromaticity criteria, the geometry-based index HOMA and the magnetic properties-based index NICS, were used to estimate the aromaticity of the complete and selected fragments of the above compounds. Results show that structure 2a, which has the H atom in position 1 of the triazole ring, has low aromaticity, although it contains structural fragments with large conjugation. The aromatic character of both tautomers 2b and 2c is similar to that of both the porphyrin and the porphyrazine. The central ring contour was found to be the most aromatic part of the triazoleporphyrazine tautomers. Occupancy of the central position of the macrocycle cavity of the triazoleporphyrazine by a metal atom increases the aromaticity of the macrocycle as a whole, but reduces the conjugation of the central cross sub-unit. In conclusion, both criteria can be used confidently for evaluating the aromaticity for the studied systems.