Blood-feeding is an ordinary way of life for many insects, but within the butterflies and moths, skin-piercing and blood-feeding are restricted to the genus Calyptra. Of the seventeen Calyptra species distributed throughout Asia, seven have been recorded attacking cattle, elephants, and humans. The remaining ten Calyptra species and closely related genera are obligate fruit-piercers. It has been hypothesized that an evolutionary progression from nectar-feeding to primary and secondary fruit-piercing has culminated in skin-piercing and blood-feeding. This hypothesis has never been tested within an empirical phylogenetic framework, and a directional progression of feeding types cannot be tested formally until the relationships of Calyptra and related genera and are known. To test the hypothesis of a directional progression of feeding types we undertook a phylogenetic analysis of Calyptra and related genera using morphological character systems from male-female pairs of 40 taxa. A preliminary phylogeny of Calyptra and closely related genera will be provided and the comparative morphology of various proboscis types will be discussed.