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

Introduction to Dock Red

Every conversation you have with an AI ends in amnesia. The model forgets you. Your history, your preferences, your relationship — gone. Dock Red exists to fix that. Dock Red is fundamentally a research program. We are focused on LLM memory and long context interactions. In this blog I will share our findings and insights. These fall into three fundamental categories, “hard”, “soft”, and “half-baked”. Our “soft science” is really an understanding of the capabilities and limitations of persistent memory AIs and how to work with them in an interactive, relationship-based way. ...

June 27, 2026 · 2 min · Braddock Gaskill