A conversation for simulation by an artificial intelligence-based tutor is automatically generated. The conversation relates to content on which the artificial intelligence-based tutor is being trained. The automatically generating the conversation includes automatically generating inputs from a simulated student regarding the content, and automatically generating on behalf of the artificial intelligence-based tutor expected responses to the inputs generated from the simulated student. The conversation is provided as an output to be input to the artificial intelligence-based tutor for simulation by the artificial intelligence-based tutor.