This study examined the use of a wearable smartwatch-based intervention to support the executive functioning needs of college students with intellectual disability and autism spectrum disorders. The study was designed to address the universal design for learning guidelines and checkpoints for Provide options for Executive Functions. Three students with intellectual disability, two on the autism spectrum, participated in this multiple-probe across participants with an embedded ABAB design to determine whether a causal relationship exists between the smartwatch intervention and the percentage of tasks completed independently. Students were taught to use a wearable smartwatch device to enter novel appointments for the coming week and the associated tasks. All students self-operated the wearable device to enter appointments, attend appointments on time, and complete associated tasks. Results are discussed in the context of applying new technology applications to assist individuals with intellectual disability and autism to self-manage technological supports to learn new skills, set reminders, and enhance independence.