Background: Individuals with intellectual disabilities (ID) show difficulties with everyday planning. A tablet-based training program for everyday planning may be a suitable intervention, but its feasibility must be evaluated. This study evaluated how behavior changes during training and if individuals with ID can use technology by themselves. Method: Thirty-three adolescents with ID and 30 younger children with a typical development were recruited. The participants were instructed to train in school for a total of 300 minutes. After the intervention, the participants were matched on mental age (MA). Results: Only 16% of the participants trained for all 300 minutes. Participants in the MA group trained for a longer time than the ID group. Both groups made fewer errors per task at the end compared to the beginning. Individuals with ID started off making less attempts per task and increased their activity during the training. This pattern was not seen in the comparison group. Conclusions: Both groups used the program independently, without adult supervision. However, a large group of participants in the ID group had a low usage time. Thus, the program might not have been feasible for that subgroup. The ID group increased their activity during the training which might mirror a strategy development of how to use the program. The change in behavior in activity on task attempts can be interpreted such that individuals with ID need a longer time to get familiarized with the technology. Tablet-based training programs are feasible for individuals with ID, but it is necessary to follow up on usage time.