Artificial intelligence (AI) tools permit humans to make bigger and more grandiose mistakes—and, so, incur new kinds of liability. Consider the attorney who used ChatGPT to generate a brief, which cited multiple nonexistent court decisions. Analyze the liabilities that may arise out of such errors—allegations of malpractice, defamation, copyright infringement, fraud and even bodily injury. Predict how insurance might respond based on real intelligence and long experience that suggest insurance companies may get creative to exclude novel claims. Examine the relevant policies that you may want to consider and the coverage defenses that you will likely find yourself resisting.