The middle-to-high-school transition and the first year of high school are critical periods in students' lives. According to the Southern Regional Education Board (SREB), "The passage of students from the middle grades to high school is the most difficult transition point in education" (2002, p. 24). Although there are many different types of grade configurations, most students make the transition into high school between eighth and ninth grade. Regardless of grade configuration, many incoming high school students are deciding whether to stay or leave school during the first weeks of the school year (Hertzog & Morgan, 1999). In this article, authors discuss the importance of middle-to-high school transitions and highlight the importance of collaboration between middle and high school teachers as essential for healthy adolescent development beyond the middle grades.