Much of early literacy education happens at home with caretakers reading books to young children. Prior research demonstrates how having dialogue with children during co-reading can develop critical reading readiness skills, but most adult readers are unsure if and how to lead effective conversations. We present ContextQ, a tablet-based reading application to unobtrusively present auto-generated dialogic questions to caretakers to support this dialogic reading practice. An ablation study demonstrates how our method of encoding educator expertise into the question generation pipeline can…