The Kentucky Valley Educational Cooperative and Green River Regional Educational Cooperative received an Investing in Innovation (i3) development grant from the U.S. Department of Education to implement the Creating College and Career Readiness (C3R) initiative. The initiative offered a suite of software developed by WIN Learning (WIN) to support college and career readiness (CCR) among students in grades 8 through 12. The Kentucky Valley Educational Cooperative engaged RAND researchers to conduct an evaluation of C3R. The evaluation consisted of implementation and impact studies that relied on a variety of data sources. The implementation evaluation focused on how schools planned to use the suite of C3R software, how many students participated in the initiative, levels of participation, and factors that enabled or hindered implementation. This study offered useful insights about planning and implementation to school-based personal and program developers interested in using educational technology in schools. [This study was sponsored by the Kentucky Valley Educational Cooperative (KVEC).]