The genus, Pupulanella, Adamski and Nishida, n. gen. is proposed, and synapomorphies are given as supportive evidence. All life stages of P. gemma Adamski and Nishida, n. sp. (Lepidoptera: Gelechioidea: Depressariidae) are described, and observations of its natural history are provided. The eggs are saddle-shaped, with several rows of shallow, parallel, and alternating longitudinal ridges and furrows, each contiguous with a transverse crest on opposing polar ends that are steeply sloped. Each egg is laid singly on the underside of leaves along the veins, and occasionally on stems or leaf petioles of the host plant, Rivina humilis L. (Petiveriaceae). The first instar and early second instar live within a weblike silken tunnel on the undersurface of leaves along the leaf veins while later instars construct and live within a partially-rolled shelter along the outer margin the leaf. Pupation occurs within a dried leaf fold in litter on the ground. The pupa is covered with short hairs, is deeply excavated between the labrum and the proximal margins of the maxillae, and possesses a ridgelike structure (= cocoon cutter) on the dorsolateral area of the prothorax. Adult moths exhibit an unusual survival behavior in microlepidoptera, by resting conspicuously on the upper surfaces of leaves exposing a “false head” and eye-spot patterned on the apical part of the forewings, on each side of the posterior end of the insect. Additionally, the terminal portions of the antennae and hindlegs extend well beyond the posterior wing margins contributing to a more realistic headlike mimic. Males and females are crepuscular, exhibiting short distance flights among host plants. Pupulanella brunniceps (Felder and Rogenhofer, 1875), n. comb. is transferred from Filinota..