This phenomenological study investigates teacher experiences using i-Ready's literacy-based software with Black male fifth-grade students in an urban school district in the Northeast region of the United States. The participant's knowledge about i-Ready is fundamental to understanding the program's impact on Black male fifth-grade students. This phenomenological study examines teacher experiences with i-Ready software and the program's use of culturally responsive education to understand literacy achievement among urban fifth-grade Black males. The researcher analyzed teachers' experiences working with fifth-grade Black males in this study. Teachers have a wealth of knowledge that will contribute to improving i-Ready's literacy-based software's impact on Black male urban fifth-grade students. Fifth grade is a transitional year into middle school, and data from the National Center for Educational Statistics (2019) and the National Assessment of Educational Progress (2022) suggest that literacy outcomes have decreased for Black male students after the fourth grade. Black males have the lowest literacy outcomes compared to other ethnic groups (National Center for Educational Statistics, 2019). Literacy-based software is heralded as an innovative and effective way to improve student literacy rates. School districts have poured thousands of dollars into programs like i-Ready to increase performance outcomes. Nevertheless, in urban school districts, the literacy rates for Black males still lag behind all gender and ethnic groups (Husband, 2012). This phenomenological study takes an intersectional look at teacher experiences using i-Ready literacy-based software and the program's cultural responsiveness. Husband (2021) tells us that culturally relevant pedagogy is crucial to developing improved literacy rates among Black males. Increasing i-Ready's cultural responsiveness will increase engagement (Frederick et al., 2009). This study will allow Curriculum Associates, developers of i-Ready, and urban school districts across the country to identify essential concepts in culturally responsive education and add them as fundamental components to the program. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]