This study investigated literacy learning in students with specific kinds of language challenges at a specific stage of schooling--transition to high school--when the language requirements of the curriculum can be especially challenging. For this exploratory research, a case study approach was adopted that compared 2 adolescent boys both with language learning problems but with 2 contrasting disabilities--autism spectrum disorder (ASD) versus oral and written language learning disability (OWL LD)--just before entry to ninth grade. Three research aims compared participants on (a) learning profiles assessed via a comprehensive psychoeducational assessment battery, (b) change in their learning profiles based on response to instruction to a computerized intervention, and (c) change in their personal narrative compositions and use of taught translation strategies collected during 6 lessons of the computerized intervention. Results indicated that participants demonstrated variable psychoeducational profiles and response to instruction that highlighted similar yet distinct patterns of strengths and weaknesses. Personal narrative writing samples showed that participants demonstrated distinct challenges, but only the participant with ASD showed no response to instruction and produced predominantly off-topic text. Results are discussed in reference to educational applications and future research design implications to understand the writing challenges experienced by children with ASD in reference to children with OWL LD or other specific learning disabilities.