The centralization of the low upgliding diphthong (typically called Canadian Raising, here just Raising), is frequently cited as an example of phonological opacity. Conditioned by a following voiceless segment, Raising continues to apply when an underlying unstressed /t/ is flapped on the surface. Dialects which have both Raising and Flapping, then, maintain the distinction between "writer" and "rider" in the quality of the vowel, rather than the voicing of the stop. Exceptions to the simplest formulation of Raising have been reported on in the past. Underapplication of Raising in pre-voiceless environments can possibly be accounted for by prosodic structure (Chambers, 1973, 1989; Jensen, 2000; Vance, 1987). However, a few reports from the Inland North (Vance, 1987; Dailey-O’Cain, 1997) and Canada (Hall, 2005) suggest that the regularity of Raising’s conditioning has deteriorated, allowing raised nuclei before underlyingly voiced segments. The distribution of these raised variants is unpredictable within a speaker’s phonology, but stable for given words, suggesting that Raising has lexicalized, and is undergoing diffusion to new environments. This paper focuses on the phonological status of Raising in Philadelphia. Raising was identified as an incipient sound change in progress in the LCV study of the 1970s, and has been revisited for study in connection with its masculine association (Labov, 2001; Conn, 2005; Wagner, 2007). After examining data from 12 boys, ages 14 through 19, it appears that Raising has lexicalized here as well. [^y] frequently appears before underlyingly voiced stops, as well as before nasals, but not in a phonologically predictable manner. Certain words seem to be selected for consistent overapplication however. "Spider" and "cider" are lexical items with raised nuclei for which there is broad agreement between speakers. However, there are also a number of lexical items which show more interspeaker variation, such as "tiny", produced variably as [tayni] or [t^yni]. Importantly, across all of the data, the effect of the lexical item on overapplication of Raising is stronger and more significant than the effect of surrounding phonological environment.