In this study, the magnetic anisotropy of metal complexes is explored for its crucial role in the development of molecular materials for cutting-edge applications in spintronics, memory storage, and quantum computing. The challenge of achieving maximum magnetic anisotropy for paramagnetic single nickel ion sites is addressed and realized through an on-surface thermally induced planarization reaction in tetraphenylporphyrin, which maintains the nickel species in a square planar coordination environment. At the same time, the effective ligand field reduction due to the increased π-conjugation results in a lower reactivity of the molecular species. The results herein reported showcase the synergy between magnetic anisotropy and chemical robustness in single-site magnetic materials, thus opening exciting prospects for the development of stable uniaxial anisotropy in these materials. Such a finding represents a relevant advance in the field and validates a protocol for exploring magnetic anisotropy in metal complexes.