Purpose: This study addressed the current policy push to improve students' college and career readiness (CCR) as manifested within the Every Student Succeeds Act (ESSA) and examined CCR policy in the state of Illinois as a case study, noting ways in which provisions for CCR programs prepare all students, including those historically underserved by higher education, to be prepared for education and employment post-high school. Research Methods: A critical analytic approach was undertaken, foregrounding equity. We conducted thematic content analysis of ESSA and Illinois policy, employing a CCR accountability paradigm. Findings: CCR-related content was contained throughout ESSA. Although content varied, themes were identified. Dual enrollment provisions were prominent in ESSA but not the Illinois' CCR laws; however, science, technology, engineering, and mathematics was emphasized in both. ESSA introduced but did not fully clarify what constitutes a well-rounded education and did not identify particular reporting and accountability provisions, whereas two Illinois' CCR bills focused on remedial education and the third evidenced a more comprehensive and integrated CCR approach. These findings suggest distinct federal and Illinois' CCR visions. A more systematic equity focus was evident within ESSA. Implications for Research, Policy, and Practice: ESSA provisions providing new flexibilities to states portend wide variation in emphasis toward, and accountability for, long-standing equity issues. District officials will also likely have substantial flexibility in their administration, design, and implementation of ESSA-funded CCR programming, which may affect educational equity in ways that advantage and disadvantage. We thus provide several cautions and recommendations.