The middle school transition has been identified as a difficult time for youths, resulting in adjustment difficulties across a variety of domains. Although some research has examined strategies that are useful for the adjustment outcomes associated with the transition, more research understanding student perceptions of what is helpful in the middle school transition and adjustment correlations of perceived level of difficulty is needed. To this end, the current study surveyed 84 youths approximately 2.5 months after their transition to middle school. Parents were perceived as helpful by almost all students (>90 percent), followed by friends, then teachers. In addition, locker time before the start of school and a tour of the middle school while still in fifth grade were endorsed as helpful by the majority of the students. Approximately 29 percent of students reported that the middle school transition was difficult, and high levels of transition difficulty were associated with poorer adjustment for both boys and girls, specifically high levels of depressive symptoms and schoolwork difficulty. The article concludes with suggestions for transition strategies.