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What do Claude's permission modes actually gate, from always-ask to skip-everything?

Last updated 2026-08-17 · Confidence: documented — Claude Code’s permission docs, the auto-mode announcement, and the Cowork/connector help center; whether Cowork’s skip mode overrides a per-tool “Needs approval” is inferred.

Both surfaces run the same ladder — manual approval per action, an auto mode where a second model reviews actions instead of you, and a skip mode with no checks — and connector write actions plus org-required approvals keep prompting on every rung.

Cowork’s three modes:

  • Manually approve — pauses for each action.
  • Automatically approve — Claude keeps working while it reviews each action for data exfiltration and prompt injection, blocking what looks unsafe — the “another model watches” mode; it consumes extra usage.
  • Skip all approvals — no pauses, no review; earlier labeled “act without asking”.

Whatever the mode, Cowork only reads and writes folders you’ve connected — its file sandbox.

The permission-modes doc: Manual (default), acceptEdits (file edits and common filesystem commands in the working folder run unprompted), read-only plan, auto, dontAsk (auto-denies anything not pre-approved — for CI), and bypassPermissions (--dangerously-skip-permissions), which the docs reserve for isolated containers and VMs.

Auto’s classifier blocks actions like curl | bash, force pushes, and sending sensitive data out. Announced March 24, 2026, generally available July 10, it became the built-in starting mode on Pro, Max, and Team on August 14, 2026 — before that, sessions started in manual.

  • Connector tools an org set to ask, and MCP tools marked requiresUserInteraction, prompt in every mode — bypass included. Deny rules block everywhere too.
  • Connector write actions (send email, share or trash Drive files) ask by default; per-tool choices — Always allow / Needs approval / Blocked — persist as settings across sessions. Whether Cowork’s skip mode overrides a per-tool Needs approval is undocumented.

Admins hold the scoping levers: managed settings can disable auto and bypass org-wide; on the desktop app, bypass needs a settings toggle on Pro/Max but org policy on Team/Enterprise; owners decide whether members may set write actions to run unprompted.

Does skip mode stop the Asana permission prompts? The routine ones, yes — but the targeted fix is setting that connector’s tools to Always allow, which kills the prompts without dropping every other check. Approvals your org requires survive every mode.