Some instructors seek to craft assignments that guide students in surpassing what AI can do. Others see that as a fool’s errand—one that lends too much agency to the software. As faculty members ponder academe’s new ChatGPT-infused reality, many are scrambling to redesign assignments. Some seek to craft assignments that guide students in surpassing what AI can do. Others see that as a fool’s errand—one that lends too much agency to the software. Either way, in creating assignments now, many seek to exploit ChatGPT’s weaknesses. But answers to questions concerning how to design and scale assessments, as well as how to help students learn to mitigate the tool’s inherent risks are, at best, works in progress.