Restaurant and grocery delivery apps are racing to turn ordering into a conversation, but early AI shopping assistants reveal a more basic challenge: chat is only as useful as the commerce infrastructure beneath it. While Instacart has had three years to learn how its users interact with its AI-based search tools, both Gopuff and DoorDash have launched conversational AI assistants over the past two weeks. These voice and text-prompted chatbots are promising to help consumers translate vague intent into completed carts. But in testing, the strongest experiences were not the ones with the most conversational UI. They were the ones with the best underlying structure: recipes, product metadata, preference capture, and retrieval logic that could actually turn a prompt into something shoppable.