A multiple probe design across participants was used to evaluate the effectiveness of progressive time delay (PTD) during small group instruction to teach social problem-solving to preschoolers and to assess generalization to novel contexts. PTD was used to teach children to both name and use a variety of problem-solving solutions. Target participants, all of whom exhibited challenging behavior or were at risk for social skill deficits, were paired with a typically developing peer for small group instructional sessions. During sessions, children were presented with scenarios involving simple social problems and were asked, “What could you do?” After naming an appropriate solution, participants were prompted to use the solution. Results indicate the use of PTD during small group instruction was effective for teaching social problem-solving to preschoolers, generalized to novel contexts and maintained following the withdrawal of the intervention. Limitations, areas for future research, and implications for practice are discussed.