The title is meant as a live question and conversation starter. Where are we going? Are we on the right path? What ecological and other constraints do we need to acknowledge? Now that we know we can make transgenic mosquitoes resistant to transmitting disease—what’s next? What are the questions we need to ask and have answered? What counts as a wise decision? How do we make wise decisions and set appropriate implementation measures? Bringing together ideas and questions from history, decision theory, and the negotiation literature, I wish to spur conversation about where we are headed, or ought to head, with transgenic mosquitoes.