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Generalizing is a fundamental practice in mathematical reasoning. Yet, research has highlighted mathematics teachers’ challenges engaging students in generalizing activity. This study explores an innovative professional development workshop designed to support secondary mathematics teachers to learn about selecting tasks that foster generalization by making connections to generalizing as a mathematical practice. I investigate changes in three secondary mathematics teachers’ knowledge of generalizing as a mathematical practice and as a teaching practice following their participation in the workshop. Participants engaged in more sophisticated generalizing actions as the workshop progressed and revised tasks in ways that engaged students in similar generalizing activity. These findings contribute to the field’s understanding of developing teaching practices for secondary mathematics by making connections to advanced mathematics.