National and state education reforms are centered on developing higher academic expectations and standards to ensure students transitions into postsecondary options, college and career ready. What does this national emphasis signify for urban school districts that are educating a significant proportion of first-generation students and that struggle to produce students ready for the rigor of postsecondary education without remediation? Framed within Karl Weick's (1976) theoretical framework of loose coupling organizational theory, this qualitative study examined the implementation of the pseudonymous ABC High School District college readiness education reform initiative through the lens of district-wide system actors, which included district leadership, school-level implementers and the students as the intended beneficiaries. ABC High School District is the largest non-unified urban school district in a large metropolitan area in the Southwestern United States. I focused specifically on two implementation sites: Blue Sky and Desert Flower High Schools. The system actors expounded on their knowledge and understanding of how they perceived the implementation of the initiative, their interpretations of the district's new policy and initiative, and how this initiative guided their practices based on their respective roles. The findings included the four major themes of (a) building capacity of the actors, (b) communication, (c) policy and politics, and (d) academic rigor and high expectations. Two additional findings specific to counselors and students were also revealed. The counselor-specific experiences revealed the changes in their roles that have created confusion among school staff and their growing responsibilities that may impede the progress of the district initiative. The student-descriptions suggest their knowledge about college and career planning, challenges, and their academic preparedness to successfully transition to a postsecondary institution.