Critical literacy instruction has been offered as a means of improving the historically low reading achievement of African American boys. This study examined the impact of two strategies, disconnections and problem posing, on the critical literacy development of upper elementary African American boys. The boys were engaged in six instructional sessions using the strategies to foster discussion. Transcripts of the boys’ discussions across the sessions demonstrate that the strategies promoted the boys’ engagement in critical discussion, including comparing the text with their own life experiences, considering relationships between characters, and exploring the potential influence of the author’s gender on the story. In a short time period, the boys made substantial progress toward critical literacy.