The purpose of this paper is to critically explore factors affecting Native Hawaiian college-going to reconceptualize and improve early college programs serving Native Hawaiians. Survey and focus group data from an internal evaluation of early college summer programs at the University of Hawai'i--West O'ahu (UHWO) provide insight into Native Hawaiian student experiences in early college and their perceptions of college-going and college readiness. Three questions guided this inquiry: (1) What kind of expectations about college do Native Hawaiian high school students see or hear in their home and community? (2) What obstacles do these students perceive in going to college? and (3) What does being college-ready mean to Native Hawaiian high school students? Starting with a reframing of the issue of the achievement gap, this article reviews literature regarding early college models, college readiness, and Indigenous experiences of college-going. It then introduces Kanaka 'Oiwi Critical Race Theory or Kanaka'OiwiCrit (Wright & Balutski, 2016; Cristobal, 2018), which provides a culturally grounded framework to analyze data and consider how systemic issues in the form of external, settler colonial consequences affect student understanding, articulation, and actions in higher education.