This study assessed the effects of portable video modeling on social interactions of four children with autism, three boys and one girl, 4- to 5-year-olds, in preschools in Iceland. Participants were shown 1-min videos on a small handheld device where a peer model initiated social interactions and played with two peers. A multiple-probe-across-participants design showed that video modeling reduced latency to social initiation and increased reciprocal play and language use per 5-min play sessions. Improvements generalized to other peers, a larger group, and to the main classroom and were maintained post intervention. These preliminary findings suggest that video modeling with a handheld device could support the acquisition and generalization of social play of preschool children with autism in natural settings.