A single-subject, alternating treatment study compared the impact of two types of photograph displays of contrasting contextual complexity. The study examined the impact of high-context and no-context photographs, displayed on an iPad, on the ability of three preschool children with autism spectrum disorder (ASD) to transition to play activities. The influence of the two photograph types on the children’s duration of transition time, number of prompts required, and type of prompts were measured. Results indicated that both photograph types provided helpful support for the children’s transition time to play activities. Results for duration of transition time and number of prompts required during transitions suggest that the participant with more challenging needs performed more quickly and independently using high-context photographs. Results suggest the photographs that have contextual information matched to a child’s needs can provide salient information and support their transition to activities in familiar settings.