External-recipient draft SOP

Hardwired 2026-05-11 PM after a full-day session that burned through 8+ failed draft attempts to ship one email to the Devine prospects. Every failure shape in that session is now structurally blocked by one of the 6 gates below. An agent that follows this SOP in order cannot reproduce any of today's failures.

The six gates

Each gate produces or consumes a cert file. The Claude Code PreToolUse hook at ~/.claude/hooks/gmail_draft_audit_gate.py blocks create_draft unless ~/Library/Application Support/SkyRun/draft_audit_pass.json is current AND was produced by claim_audit_passer.py with ALL gates satisfied.

The full workflow

STEP 1 — Compose body
  Write the body text to disk at /tmp/<deal>_body.txt
  Body must contain ZERO forward commitments unless each has a verified
  deliverable file/data/capability that exists right now.

STEP 2 — Identify every factual claim
  Write claims JSON to /tmp/<deal>_claims.json with each claim mapped to
  a primary source citation (gmail:, transcript:, hs:, sot:, track:,
  keydata:, calendar:, sms:, walkthrough:, operator_directive:,
  public_record:, sla_capability:, or memory_file:+verified).

STEP 3 — Latest-inbound cert
  Call Gmail MCP get_thread on the candidate thread to verify the
  most-recent inbound message ID. Run:
    latest_inbound_check.py
      --recipient <email>
      --expected-msg-id <msg_id>
      --out /tmp/<deal>_inbound_cert.json

STEP 4 — No-stacking cert (MCP-AUTHORITATIVE — NOT UI-based)
  Call Gmail MCP list_drafts with query "to:<recipient>".
  Persist the JSON response to /tmp/<deal>_mcp_drafts.json.
  If the response shows ANY existing drafts: operator deletes them manually
  via Gmail UI, then re-fetch list_drafts and re-persist.
  Then run:
    gmail_draft_purge.py
      --recipient <email>
      --thread-id <thread_id>
      --gmail-mcp-drafts-json /tmp/<deal>_mcp_drafts.json
      --out /tmp/<deal>_nostack_cert.json

STEP 5 — Full 5-gate audit
  Run:
    claim_audit_passer.py
      --body-file /tmp/<deal>_body.txt
      --claims-file /tmp/<deal>_claims.json
      --to <to_email>  --cc <cc_email>
      --reply-to-message-id <msg_id>
      --latest-inbound-cert-file /tmp/<deal>_inbound_cert.json
      --no-stacking-cert-file /tmp/<deal>_nostack_cert.json
      --no-forward-commitments  (if body has zero forward commits)
      OR --commitments-backing-file /tmp/<deal>_backing.json
  Audit-passer writes draft_audit_pass.json valid for 180s.

STEP 6 — create_draft within 180-second pass window
  Hook checks pass file; if valid, allows create_draft.
  Returns Gmail draft ID.

STEP 7 — POST-create body persistence verification
  Call Gmail MCP get_thread (FULL_CONTENT) on the thread.
  Persist response to /tmp/<deal>_thread_postcreate.json (<120s).
  Run:
    draft_body_verify.py
      --expected-body-file /tmp/<deal>_body.txt
      --thread-json-file /tmp/<deal>_thread_postcreate.json
      --draft-id <draft_id>
      --out /tmp/<deal>_body_verify_cert.json
  Three possible statuses:
    verified — plaintextBody matches; safe to send
    lagging  — plaintextBody not yet indexed but snippet shows match;
               operator visually verifies in Gmail UI
    empty    — body did NOT persist; delete draft, retry or pivot to
               manual-paste path

STEP 8 — Operator opens Gmail UI, eyeballs, sends
  Never assert "the draft is in Gmail and complete" until operator
  visually confirms.

Anti-patterns this SOP closes (today's failures, indexed)

What to do when a gate refuses

• Gate 1 refusal → either find a primary source for the claim or remove the claim from the body.
• Gate 2 refusal → re-query Gmail MCP get_thread for the recipient, find the actual latest inbound, regenerate cert with correct msg_id.
• Gate 3 refusal → existing drafts present. Operator manually deletes via Gmail UI, re-fetch list_drafts, re-run purge script.
• Gate 4 refusal → rewrite the offending phrases. The error message names every phrase + the structural reason. Convert section labels to prose; replace performative phrases with direct statements.
• Gate 5 refusal → either remove the forward commitment from body OR produce a verified deliverable + add it to a commitments backing file.
• Gate 6 empty status → delete the draft (operator-side), switch to manual-paste path: print body inline in chat, operator pastes into Gmail Web reply UI directly.

What this SOP does NOT cover

• Calendar conflict pre-check before proposing meeting times. If a body proposes specific meeting times, the agent should ideally query Calendar via the Calendar MCP to verify Joseph isn't already booked. This is a known gap — should be added as a Gate 0 pre-flight if it becomes a recurring failure shape. (Today's draft proposed times without verifying availability; Joseph can self-correct if conflicts exist.)
• Operator-side chat-output discipline. R-29 covers the agent's chat responses to Joseph (mandatory verified_this_turn block, zero guessing words, inline citations). R-31 specifically covers methodology claims in chat. Together they discipline what the agent says to Joseph, but response_gate.py is the operator-runnable audit, not a structural gate.

Maintenance

• Any new failure shape that slips through these 6 gates → add to the failure inventory in this file + identify which gate should have caught it + extend or add a gate.
• Gate scripts live at ~/Library/Application Support/SkyRun/:

• Hook script at ~/.claude/hooks/gmail_draft_audit_gate.py
• Audit history at ~/Library/Application Support/SkyRun/audit_history/ (every audit pass record preserved)

Cross-references

• RULES.md — R-23 (primary source), R-29 (mandatory response format), R-30 (KeyData access), R-31 (no invented methodology)
• pre_task_checklist.md — pre-task 5-question gate
• feedback_drafting_standard.md — Phase 1/2/3 drafting discipline (Phase 2 freshness re-sweep, Phase 3 linter chain)
• reference_voice_anti_patterns.md — canonical anti-pattern catalog