Employment enhances community integration and overall quality of life for individuals with intellectual and developmental disabilities (IDD). Rapidly evolving and widely used handheld technologies (e.g., tablets and smart phones) may empower improved outcomes of vocational training for individuals with IDD. This systematic review summarizes and evaluates peer-reviewed studies that involved handheld technology to facilitate vocational training in authentic community-based settings for people with IDD. Eleven studies involving 32 participants with IDD were systematically located and analyzed in terms of key variables, study rigor, and Tau-U effect size estimates. Overall, Tau-U score suggested a large to a very large effect for interventions involving handheld technologies to teach vocational skills. Results are used to offer preliminary guidance for practitioners and to suggest directions for future research and practice.