This dissertation examines the salient tensing of /ɪ/ and /ʊ/ in 17 students that study at the University of Puerto Rico at Mayaguez (UPRM). Inspired by Labov’s study of Social Stratification of New York City English (1966), these variables are elicited through a series of tasks that range in levels of formality: minimal pairs, word list, reading passage, and interview tasks. Social factors, such as language identity and educational background are taken into account in search of an indexical relationship between “island identity” and phonetic production. Participants are divided into two groups: (1) those who have received English-bilingual education, and (2) those who have received Spanish-monolingual education. Attitudinal data was collected by means of an attitude survey and an interview task. Results suggest that monolinguals tensed /ɪ/ more than bilinguals and carried a stronger sense of Spanish identity. However, the tensing of /ʊ/ displayed little or no indexical correlation in the data, moreover behaved unpredictably before a lateral. Moreover, attitudinal results also yielded variation within the monolingual group, which challenges previous notions made of “language resistance” (Clachar, 1997; Barreto, 2000; Pousada, 2000; Dubord, 2007).