A back-pressure ladder with three named rungs

Osmani decomposes a loop into five primitives plus state: automations, worktrees, skills, connectors, subagents, and somewhere to keep what is done across runs. He builds a three-rung ladder on top. Rung one is interactive, with a human in the inner loop. Rung two is supervised autonomy, where you approve the plan once and the agent implements every task, pausing on failures. Rung three is an unattended loop with a separate checker grading the result and a human reviewing evidence at the boundary. The rule for moving between them: "hand a loop only as much autonomy as you can cheaply and reliably verify, and not one inch more."

He then makes the dark factory a per-loop switch rather than a setting. "A dark factory ships code no human has read, verified only by other machines." Lights out is fine where the check is a cheap, hard-to-fake oracle and the loop is roughly three to ten steps. Lights stay on for auth, secrets, public contracts, migrations, and behaviour that "lives in the scars, not the code." Three costs are named as growing with smoothness: cognitive surrender ("a loop that runs itself makes it tempting to accept whatever it returns"), comprehension debt, and the orchestration tax. The piece opens with a quote attributed to Boris Cherny, who leads Claude Code at Anthropic, about writing loops rather than prompts. It carries no first-party link, so treat it as Osmani's attribution.

Why it matters: the ladder converts "how much autonomy" from a taste question into a verification question, which is the only version of it that can be answered. Read it knowing it is documentation for the author's own MIT-licensed skills pack, and that nothing in it is measured.