The purpose of this article is to investigate the potential role of parent involvement and parent expectation in postschool outcomes for individuals who are d/Deaf or hard of hearing (DHH). Students who are DHH have lower retention and employment rates than their peers. Recognizing the importance of family in developmental outcomes for all individuals, this article focuses specifically on the role of parents in facilitating postsecondary outcomes. In an effort to address gaps in the literature in this area, this study utilizes the National Longitudinal Transition Survey 2 (NLTS-2) dataset to measure the effect of parental involvement and expectations as individuals who are DHH transition from secondary grades into a variety of postschool settings. Overall, none of the parental involvement variables were statistically significant when controlling for student and parent demographics. The parental expectation variables that had a statistically significant impact on outcomes included expectations to live independently, to be employed, and to pursue postsecondary education. This article discusses findings in the context of operationalization of study constructs in the NLTS-2 and literature related to transition and parental involvement for students who are DHH.