There is urgency for minority serving rural hybrid community colleges for innovation in offering cybersecurity education to local high school students who have no access to these emerging occupations. Focusing on high school women and minorities, this case study uses field experiences to drive an iterative improvement process that enhances the delivery of online pedagogical and learning design in a tri-island county. Beginning in Fall 2016, the project, implements an early college cybersecurity career pathway, targeting the low access of women and minorities at the high schools pursuing higher education cybersecurity programs by: enrolling 84 high school students in an online sequence of college cybersecurity courses over four semesters. The intent of the case study is to determine how and why things work (including identifying the contextual constraints) within university-high school partnerships aimed at closing the skills gap for women and minorities for cybersecurity jobs while in high school. Our iterative effort has led us to explore deeper issues around innovation in online pedagogies while focusing on the underrepresentation in cybersecurity. This paper serves as an example of an exploratory researcher-practitioners and iterative design specifically within an early college context across educational sectors (e.g., high school and college). The study promotes a better understanding of how to embrace discovery to provide all high school students access to advanced technology educational opportunities like cybersecurity.