The Rumsfeld Paradox

Donald Rumsfeld: “there are known knowns; there are things we know we know. We also know there are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns—the ones we don’t know we don’t know. [..] it is the latter category that tends to be the difficult ones.” The Problem Have you ever given an LLM the instruction “If you don’t know something, do a web search!” Or, “If you are uncertain, ask me!” These actually rarely work well. Sometimes an LLM will recognize a SITUATION that might induce a web search, but that is a behavioral training condition more than a recognition of absence. ...

June 28, 2026 · 6 min · Braddock Gaskill