While innumerable factors may impede a former foster student’s educational or vocational success, less empirical attention has focused on systemically exploring psychosocial attributes among this resilient population. Utilizing a Strengths-Based Assessment (SBA) framework, this study expands upon recommendations for holistic and resiliency-informed assessments among former students in foster care. This pilot study informs a longitudinal investigation to systematically identify patterns of well-being among a highly resilient group of students pursuing post-secondary degrees. An exemplar multifaceted, strength-based framework with robust psychometric properties and international applications, known as Covitality, offers a promising framework for measuring well-being from the college student’s perspective. Partnering with a community organization aims of this study include: (a) uncover patterns of well-being among a culturally rich and resilient population using a holistic measure of well-being (i.e., SEHS-HE), (b) identify positive psychological interventions uniquely tied to Covitality data, and (c) highlight qualitative feedback to amplify student voice and well-being promotion. 156 former foster youth responded to the SEHS-Higher Education (SEHS-HE) survey across two periods (Spring 2019, n = 80, and Spring 2021, n = 76). Data analytic methods included (1) descriptive statistics and parametric testing at wave one and (2) longitudinal analyses. Results from wave one participants indicate statistically significant differences (p < .05) in total Covitality by ultimate career goal, and Covitality significantly predicted life satisfaction among former foster youth. Implications for practice, positive psychological interventions, limitations, and future directions are offered to propel efforts towards centering resiliency, well-being, and educational success.