Social skills training for youth with learning disabilities in transition from school to work is of substantial importance. To examine the generalization of such training to real employment settings, this study used a multiple-baseline design to investigate the effects of 12 measured behaviors (3 behaviors per student) on four high school seniors. An initial simulated social skills package delivered at school led to generalization in 8 of 12 behaviors. Subsequently, in situ training at the work site produced generalization in 4 of 6 behaviors. This two-phase model appears to be a powerful way to promote generalization of behavioral skills.