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The synthesis and redox properties of first generation S-confused isophlorins are described. Despite structural resemblance to a confused porphyrin, spectroscopic and computational studies reveal weak paratropic ring current effects in these 20π macrocycles. They display redox properties atypical of parent tetrathia isophlorins. Experimental evidence supports the oxidation of an unstable 19π neutral radical, as a transient intermediate, for the formation of a unique 18π aromatic monocationic species. Spectroscopic and structural characterization revealed the substituent dependent macrocycle oxidation unfamiliar to the chemistry of antiaromatic isophlorinoids.