The perspectives of both teachers and principals are valuable in understanding to what extent recent graduates from formal educator preparation programs are ready to take on teaching roles and tasks as a teacher. The understanding gained may contribute to bettering initiatives targeted on teacher retention, particularly in those critical beginning years of practice. This study examined the perceived effectiveness of first-year teachers' preparation from the perspectives of the teachers and the principals, utilizing three-year survey data of 644 first-year teachers who graduated from a higher education institution and 497 hosting principals in a Midwest state. The findings note that the first-year teachers and principals, in general, had similar views regarding the preparation of the teachers. Significant differences were found related to certain competency domains as identified in the state's teaching standards. Also discussed in the article are longitudinal trends and recommendations for addressing noted challenges faced by first-year teachers.