When the author first started teaching twenty years ago, he thought that as long as he was using dynamic geometry software (DGS) for students to "discover" conjectures instead of them learning the conjectures from a lecture or the textbook, he was maximizing their learning potential because they were using technology. Over the years, he realized that using DGS was much more nuanced than that. Particularly the kind of tasks he had students complete was an important factor in student learning. This article describes how the Dynamic Geometry (DG) tasks that he uses with his students has evolved over his career and what he wish he had known about implementing DG tasks when he began teaching.