outreach: voice by-purpose (larger sample) + Tier-B Gmail draft creation (v0.1.0:71)
(1) Voice: _voice_examples now picks the sender's prior sent emails OF THE SAME PURPOSE (PURPOSE_PATTERNS keyword cues per outreach type), larger sample (8) weighted by purpose then recency — not just recent. meta carries on_topic for transparency. (2) Tier-B sending (gmail.compose now authorized in Workspace DWD). New email_integration/compose.py create_outreach_draft: mints a compose-scoped DWD token for the sender (credentials._mint/access_token_for parameterized by scope; GMAIL_COMPOSE_SCOPE), builds an RFC822 message, and POSTs gmail.drafts.create into the SENDER's mailbox — as an in-thread reply (threadId + In-Reply-To/References, recipient = matched LP address) when there's an active thread, else a fresh email. NEVER sends — the human sends from Gmail (guardrails #4, #6). Route POST /api/outreach/gmail-draft; UI "Create Gmail draft" button + "Open Gmail Drafts" link. Tests: test_compose.py (parse/reply-target/RFC822+threading). Message construction unit-verified; the live drafts.create runs on the box. Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>
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Keysat
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"""Create a Gmail DRAFT (never send) in the sender's mailbox via domain-wide delegation
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with the gmail.compose scope. Lets an approved Outreach draft land in the user's Gmail
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(and therefore Superhuman) Drafts — as an in-thread reply when there's an active thread,
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or a fresh email otherwise. The human reviews and sends from Gmail (guardrails #4, #6 —
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our code only ever creates a draft, it never sends).
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"""
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import base64
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import email.message
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import json as _json
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import urllib.error
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import urllib.parse
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import urllib.request
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from . import config as _cfg
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from . import credentials as _creds
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def _parse_subject_body(draft_text):
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"""Split a draft of the form 'Subject: ...\\n\\n<body>' into (subject, body)."""
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text = (draft_text or "").strip()
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lines = text.split("\n")
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if lines and lines[0].lower().startswith("subject:"):
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subject = lines[0].split(":", 1)[1].strip()
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body = "\n".join(lines[1:]).lstrip("\n")
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return subject, body
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return "", text
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def _reply_target(conn, investor_id):
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"""LP address + active-thread headers for an in-thread reply, from the most recent
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matched email with this investor. Returns {to, thread_id, in_reply_to} or None."""
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try:
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row = conn.execute(
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"SELECT e.rfc_message_id, e.gmail_thread_id, l.matched_address "
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"FROM emails e JOIN email_investor_links l ON l.email_id = e.id "
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"WHERE l.fundraising_investor_id = ? AND e.is_matched = 1 "
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"ORDER BY e.sent_at DESC LIMIT 1", (investor_id,)).fetchone()
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except Exception:
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return None
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if not row or not row["matched_address"]:
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return None
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return {"to": row["matched_address"], "thread_id": row["gmail_thread_id"],
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"in_reply_to": row["rfc_message_id"]}
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def _build_raw(from_addr, to_addr, subject, body, in_reply_to=None):
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msg = email.message.EmailMessage()
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msg["From"] = from_addr
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msg["To"] = to_addr
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msg["Subject"] = subject or "(no subject)"
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if in_reply_to:
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msg["In-Reply-To"] = in_reply_to
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msg["References"] = in_reply_to
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msg.set_content(body or "")
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return base64.urlsafe_b64encode(msg.as_bytes()).decode("ascii")
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def create_outreach_draft(conn, sender_email, investor_id, draft_text):
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"""Create a Gmail draft in `sender_email`'s mailbox addressed to the investor.
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Returns {status, ...}. Never sends."""
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if not sender_email:
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return {"status": "no_sender"}
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if not _cfg.CONFIG.enabled:
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return {"status": "integration_disabled"}
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subject, body = _parse_subject_body(draft_text)
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if not body.strip():
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return {"status": "empty"}
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target = _reply_target(conn, investor_id)
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if not target:
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return {"status": "no_recipient"} # no email history -> no LP address to draft to
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try:
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provider = _creds.build_provider(lambda: conn)
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token = provider.access_token_for(sender_email, _creds.GMAIL_COMPOSE_SCOPE).token
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except Exception as exc:
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return {"status": "auth_error", "reason": str(exc)}
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raw = _build_raw(sender_email, target["to"], subject, body, target.get("in_reply_to"))
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payload = {"message": {"raw": raw}}
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if target.get("thread_id"):
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payload["message"]["threadId"] = target["thread_id"]
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url = f"https://gmail.googleapis.com/gmail/v1/users/{urllib.parse.quote(sender_email)}/drafts"
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req = urllib.request.Request(url, data=_json.dumps(payload).encode("utf-8"), method="POST",
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headers={"Authorization": f"Bearer {token}",
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"Content-Type": "application/json"})
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try:
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with urllib.request.urlopen(req, timeout=20) as resp:
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_json.loads(resp.read())
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except urllib.error.HTTPError as e:
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return {"status": "gmail_error", "reason": e.read().decode("utf-8", "replace")[:300]}
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except Exception as exc:
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return {"status": "gmail_error", "reason": str(exc)}
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return {"status": "ok", "to": target["to"], "threaded": bool(target.get("thread_id")),
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"gmail_url": "https://mail.google.com/mail/u/0/#drafts"}
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@@ -32,6 +32,9 @@ from . import errors
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GMAIL_READONLY_SCOPE = "https://www.googleapis.com/auth/gmail.readonly"
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# Drafts scope (authorized in Workspace DWD). We only ever CREATE drafts with it; the
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# human sends from Gmail. (Google bundles send into this scope, but our code never sends.)
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GMAIL_COMPOSE_SCOPE = "https://www.googleapis.com/auth/gmail.compose"
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GOOGLE_TOKEN_URL = "https://oauth2.googleapis.com/token"
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@@ -61,13 +64,14 @@ class DWDCredentialProvider:
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self._cache: dict[str, AccessToken] = {}
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self._lock = threading.Lock()
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def access_token_for(self, email_address: str) -> AccessToken:
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def access_token_for(self, email_address: str, scope: str = GMAIL_READONLY_SCOPE) -> AccessToken:
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key = f"{email_address}|{scope}"
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with self._lock:
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cached = self._cache.get(email_address)
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cached = self._cache.get(key)
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if cached and cached.expires_at - time.time() > 60:
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return cached
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token = self._mint(email_address)
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self._cache[email_address] = token
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token = self._mint(email_address, scope)
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self._cache[key] = token
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return token
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def revoke(self, email_address: str) -> None:
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@@ -78,7 +82,7 @@ class DWDCredentialProvider:
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# ------------------------------------------------------------------ helpers
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def _mint(self, subject_email: str) -> AccessToken:
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def _mint(self, subject_email: str, scope: str = GMAIL_READONLY_SCOPE) -> AccessToken:
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try:
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from cryptography.hazmat.primitives import hashes, serialization # type: ignore
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from cryptography.hazmat.primitives.asymmetric import padding # type: ignore
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@@ -92,7 +96,7 @@ class DWDCredentialProvider:
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claim = {
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"iss": self._client_email,
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"sub": subject_email,
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"scope": GMAIL_READONLY_SCOPE,
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"scope": scope,
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"aud": GOOGLE_TOKEN_URL,
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"iat": now,
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"exp": now + 3600,
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@@ -0,0 +1,62 @@
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#!/usr/bin/env python3
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"""Test the Gmail-draft message construction (the part that doesn't need live Gmail):
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subject/body parsing, reply-target resolution, and the RFC822 build incl. threading
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headers. The actual drafts.create call is exercised on the box. Synthetic data only.
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Run: cd backend && python3 email_integration/test_compose.py
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"""
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import base64
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import os
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import sqlite3
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import sys
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sys.path.insert(0, os.path.dirname(os.path.dirname(os.path.abspath(__file__))))
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from email_integration import compose as cp # noqa: E402
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FAILS = []
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def check(cond, msg):
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print((" PASS " if cond else " FAIL ") + msg)
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if not cond:
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FAILS.append(msg)
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def main():
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s, b = cp._parse_subject_body("Subject: Following up\n\nHi Sarah,\n\nthanks for the call.")
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check(s == "Following up" and b.startswith("Hi Sarah"), "parses 'Subject:' line + body")
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s2, b2 = cp._parse_subject_body("No subject prefix here")
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check(s2 == "" and b2 == "No subject prefix here", "no subject line -> empty subject, full body")
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c = sqlite3.connect(":memory:")
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c.row_factory = sqlite3.Row
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c.executescript("""
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CREATE TABLE emails(id TEXT, rfc_message_id TEXT, gmail_thread_id TEXT, sent_at TEXT, is_matched INT);
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CREATE TABLE email_investor_links(email_id TEXT, fundraising_investor_id TEXT, matched_address TEXT);
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""")
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c.execute("INSERT INTO emails VALUES('e1','<m1@x>','t1','2026-06-01',1)")
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c.execute("INSERT INTO email_investor_links VALUES('e1','inv1','lp@harborvine.example')")
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c.commit()
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t = cp._reply_target(c, "inv1")
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check(t and t["to"] == "lp@harborvine.example" and t["thread_id"] == "t1" and t["in_reply_to"] == "<m1@x>",
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"reply target resolves LP address + thread + in-reply-to")
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check(cp._reply_target(c, "nope") is None, "no history -> no reply target")
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raw = cp._build_raw("grant@ten31.xyz", "lp@x.example", "Hi", "Body text here", "<m1@x>")
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dec = base64.urlsafe_b64decode(raw).decode("utf-8", "replace")
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check("From: grant@ten31.xyz" in dec and "To: lp@x.example" in dec, "RFC822 has From + To")
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check("Subject: Hi" in dec and "Body text here" in dec, "RFC822 has Subject + body")
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check("In-Reply-To: <m1@x>" in dec and "References: <m1@x>" in dec, "threading headers set for replies")
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raw2 = cp._build_raw("a@b.co", "c@d.co", "", "body", None)
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dec2 = base64.urlsafe_b64decode(raw2).decode("utf-8", "replace")
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check("Subject: (no subject)" in dec2 and "In-Reply-To" not in dec2, "no subject / no thread -> fresh email")
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if FAILS:
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print(f"\nFAILED ({len(FAILS)})")
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for f in FAILS:
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print(" - " + f)
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sys.exit(1)
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print("\nALL PASS (gmail compose message construction)")
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if __name__ == "__main__":
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main()
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