The ‘aegrota species group’ of the Neotropical nymphalid genus Caeruleuptychia Forster, 1964, in addition to three other superficially similar, enigmatic species in the genus, are revised. A lectotype is designated for Euptychia aegrota Butler, 1867, E. aetherialis Butler, 1877 stat. rev., E. helios Weymer, 1911 and E. pilata Butler, 1867, and C. aetherialis is resurrected from its synonymy with C. aegrota. Caeruleuptychia helios caelestissima Brévignon, 2010, syn. nov., and Magneuptychia keltoumae Brévignon & Benmesbah, 2012, syn. nov. are both regarded as junior subjective synonyms of C. helios (Weymer, 1911), as a result of the discovery and first illustration of the female of this taxon. The female of C. aegrota is also described and illustrated for the first time, and three new species, C. trembathi Willmott, Nakahara, Hall & Neild, sp. nov., C. scripta Nakahara, Zacca & Huertas, sp. nov., and C. maryzenderae Lamas & Nakahara, sp. nov. are described and named. We analyze morphological and molecular data separately, in addition to combining morphological data with molecular data, to provide the first phylogenetic hypothesis for the taxa treated in this revision.