The Gouterman four-orbital model has long provided a foundation for understanding so-called normal porphyrin spectra. In essence, the model describes two HOMOs and two LUMOs that are energetically well separated from all other molecular orbitals, such that the electronic absorption spectrum can be understood in terms of transitions among these four orbitals. Of course, there are numerous exceptions to the model, most commonly when there are transition metals encapsulated within the porphyrin core and their d orbitals impinge in the same energy space as the four Gouterman frontier orbitals. Hypsoporphyrins exhibit blueshifted spectral features relative to normal porphyrins, while hyperporphyrins exhibit redshifted spectral features and/or extra bands relative to normal porphyrins. There are also many examples of free-base porphyrins that exhibit hyperporphyrin effects, most commonly with strongly electron-donating substituents that can be either protonated or deprotonated. For example, centrally diprotonated meso-tetrakis(4-aminophenyl)porphyrin (H2[TAPP]) exhibits a dramatic hyperporphyrin spectrum with a strong NIR transition attributed to charge transfer from the aminophenyl groups to the dipositive porphyrin core. A qualitatively similar, but weaker, effect is observed for deprotonated meso-tetrakis(4-hydroxyphenyl)porphyrin (H2[THPP]), in which the anionic phenoxide substituents conjugatively inject negative charge into the neutral porphyrin core. These effects can be qualitatively appreciated with simple resonance forms. Gouterman defined three fundamental types of resonance forms for situations in which meso substituents interact with the porphyrin p-system. Type A resonance forms do not show conjugation with meso substituents while Type B or Type C show one or two such interactions, respectively. This led us to consider situations in which there could be as many as all four of the meso substituents engaged in resonance interactions with the porphyrin core. Such structures have been generated with oxidized porphyrin analogs such as oxoporphyrinogens, but are largely unknown for unoxidized porphyrins. With these considerations in mind, one of our research groups synthesized free-base 5,10,15-tris(4-aminophenyl)-20-(4pyridyl)porphyrin (H2[TA3PyP]). The molecule has eight nitrogen atoms, of which the pyridyl nitrogen is most basic, followed by the two unprotonated porphyrin nitrogens. Protonation of these three sites results in a structure for which numerous resonance forms may be written, including the classic Types A, B, and C, as well as a novel form that we have called Type D, in which all four of the meso substituents are involved in resonance. In the Type D form, two aminophenyl groups delocalize as usual to stabilize the protonated porphyrin nitrogens while the third aminophenyl group delocalizes with the pyridinium substituent through the porphyrin core (Scheme 1).