This study evaluated the efficacy of video modeling delivered via a handheld device (video iPod) and the use of the system of least prompts to assist elementary-age students with transitioning between locations and activities within the school. Four students with autism learned to manipulate a handheld device to watch video models. An ABAB withdrawal design was used to evaluate a functional relation between video modeling and the percentage of independent transitions by the student. The data indicate that all participants began transitioning more independently after the intervention was introduced and that their performance decreased with withdrawal of intervention. These results are presented in the context of how a portable video delivery system can aid students who spend considerable portions of their day in general education settings where traditional means of delivering video models (e.g., televisions and computers) may not be as accessible.