A person’s spoken language variety affects many aspects of their life, one of which is their educational experience and school trajectory. The variety a student uses may impact their academic success, especially when the variety is considered non-standard. For example, a student may fail a language test for using non-standard expressions that are generally considered incorrect despite being valid dialectal variations of the language. This dissertation focuses on the language practices and ideologies shown by Puerto Rican youth in Hampden County, MA, where we see some of the highest populations of Puerto Ricans in the mainland U.S. Furthermore, Hispanic students represent 81% of the total student population in the Holyoke Public School system, making it crucial to have a better understanding of how students’ linguistic practices may affect their educational experiences and success. Because Puerto Rican Spanish often diverges from ‘standard’ Spanish, high school students who use this variety, whether they are heritage or firstgeneration speakers, may experience discrimination or be subject to certain ideologies around their language. This dissertation has two main aims: first, to describe the language uses of youth speakers of Puerto Rican Spanish in Western Massachusetts according to salient linguistic features traditionally documented in this Spanish variety. The linguistic features under analysis are phonological –/s/ weakening, lateralization of coda /ɾ/, and velar realization of /r/–, morphosyntactic –the presence or absence of subject pronouns, uninverted wh-questions, and pre-posed infinitives–, and lexical. The second aim of this dissertation is to examine the language ideologies of these speakers, as well as the ideologies encountered in academic settings, to understand how these linguistic practices are tied to their educational experiences in relationship to Spanish. A sociolinguistic interview and two production tasks –a map task and a wh-question task– were designed and used to collect data. Nineteen participants were recorded averaging 40 minutes for each recording, resulting in a total of 8,601 tokens of /s/, 2,842 tokens of coda /ɾ/, 651 tokens of /r/, 4,044 instances of possible subject pronouns, and 190 wh-questions. For the linguistic ideologies analysis, the sociolinguistic interviews were analyzed using Critical Discourse Analysis.