Studying historically underrepresented populations can be challenging, especially for doctoral students or early career scholars, who have often been taught more "traditional" research methods. In this article, we outline challenges that we faced when conducting qualitative research on three different historically underrepresented populations, i.e., Asian/American gay, lesbian, bisexual students, doctoral students of color, and Black students at HBCUs, and how we addressed those challenges in order to complete our respective research studies. Some of these issues include recruitment of participants, maintaining confidentiality, and gaining participant trust. We conclude by discussing implications and suggest strategies for future researchers who wish to conduct similar studies.