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Social support has been identified as an important component of planning for careers among high school students. Lent, Brown, and Hackett (2000) advocated for the importance of this support within Social Cognitive Career Theory (SCCT). These authors identified a need for further research with better measurement for examining contextual support and its connection to career decision-making. Ali et al. (2011) developed a set of measures to address this need for better measurement, but identified the need for more nuanced examination of specific types of contextual support. The current study was designed to assess the importance of nuanced measuring of different types of support in career-decision making. Specifically, two scales, School Personnel and Community, from the Contextual Support of Post Secondary Planning Scales (CSPSPS) are analyzed using confirmatory factor analysis to force the scales into the factor structures proposed by Ali et al. (2011). Additionally, exploratory factor analysis was used to further examine the school personnel scale. Finally, interventions to aid School Personnel and Community in ways to support students in career decision-making are considered.