A sample of 356 children recruited from Head Start (58% European American, 25% African American, and 17% Hispanic; 54% girls; M age = 4.59 years) were followed longitudinally from prekindergarten through fifth grade. Latent profile analyses of teacher-rated inattention from kindergarten through third grade identified four developmental trajectories: stable low (53% of the sample), stable high (11.3%), rising over time (16.4%), and declining over time (19.3%). Children with stable low inattention had the best academic outcomes in fifth grade, and children exhibiting stable high inattention had the worst, with the others in between. Self-regulation difficulties in preschool (poor executive function skills and elevated opposition-aggression) differentiated children with rising versus stable low inattention. Elementary schools characterized by higher achievement differentiated children with declining versus stable high inattention. Boys and children from single-parent families were more likely to remain high or rise in inattention, whereas girls and children from dual-parent families were more likely to remain low or decline in inattention.