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As education policies evolve to address workforce demands, College, Career, and Military Readiness (CCMR) has become a cornerstone of accountability frameworks in Texas. This study examines the shifting landscape of CCMR policies within the state’s A-F accountability rating system, analyzing their implications for equity and postsecondary preparedness. Through document and narrative analyses of legislative records and advisory committee discussions from 2015 to 2024, we explore how Texas policymakers and education leaders have defined and measured CCMR over time. Findings reveal that CCMR expansion has been shaped by legislative mandates, evolving federal requirements, and stakeholder input, often balancing transparency with complexity. Equity concerns emerged as a key theme, particularly regarding access to career and technical education pathways, military enlistment, and industry-based certifications. However, persistent challenges—such as disruptions from the COVID-19 pandemic, inconsistencies in measuring readiness, and disparities in resource availability across districts—highlight the need for more targeted and adaptable policies. This research contributes to ongoing discussions about how states can design accountability systems that equitably and effectively prepare students for diverse postsecondary opportunities.