v0.18.0 Slice 1: build_envelope helper + unit tests

Per the v0.18.0 email + webhook hygiene proposal (~/git/ohm-infra/RFC-APP-EMAIL-HYGIENE-PROPOSAL.md §1), this is the shared envelope builder every send path will call in Slice 2. No call-site changes yet — Slice 2 migrates email_otc / email_invite / email._deliver / email._send_bundle to use it. The helper centralizes the deliverability-critical headers (Date, Message-ID, Auto-Submitted) and exposes per-kind unsubscribe semantics (none for OTC, mailto: for invites, full one-click for watcher notifications) as explicit kwargs rather than buried in each call site. 15 new unit tests covering: always-present headers, Auto-Submitted toggle, the three List-Unsubscribe shapes, plain-only vs multipart/alternative body. Full suite: 267 passed (was 252).
2026-05-28 07:15:06 -07:00
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+"""Unit tests for `app.email_envelope.build_envelope` (v0.18.0 Slice 1).
+
+These tests don't spin up the FastAPI app or touch the DB — they
+exercise the helper directly. The integration tests in
+test_otc_vertical / test_admin_create_user_invite_vertical /
+test_notifications_vertical exercise the helper's *use* via the
+shared `_SENT` buffer (the send path appends the envelope dict
+before invoking the helper).
+"""
+from __future__ import annotations
+
+from email.utils import parsedate_to_datetime
+
+from app.email_envelope import build_envelope
+
+
+def _base_kwargs(**overrides):
+    base = dict(
+        to_address="recipient@example.com",
+        from_address="notifications@ohm.wiggleverse.org",
+        from_name="OHM",
+        subject="A test subject",
+        body_plain="Hello, world.\n",
+    )
+    base.update(overrides)
+    return base
+
+
+# ---------------------------------------------------------------------------
+# Always-present headers
+# ---------------------------------------------------------------------------
+
+
+def test_envelope_sets_from_to_subject():
+    msg = build_envelope(**_base_kwargs())
+    assert msg["To"] == "recipient@example.com"
+    assert msg["Subject"] == "A test subject"
+    # `From` is the display-form: "OHM <notifications@ohm.wiggleverse.org>".
+    assert "OHM" in msg["From"]
+    assert "<notifications@ohm.wiggleverse.org>" in msg["From"]
+
+
+def test_envelope_sets_date_header_parseable():
+    msg = build_envelope(**_base_kwargs())
+    raw = msg["Date"]
+    assert raw, "Date header must be set"
+    # parsedate_to_datetime raises ValueError on malformed input.
+    dt = parsedate_to_datetime(raw)
+    assert dt is not None
+
+
+def test_envelope_sets_message_id_with_from_domain_by_default():
+    msg = build_envelope(**_base_kwargs())
+    mid = msg["Message-ID"]
+    assert mid, "Message-ID must be set"
+    # Shape per RFC 5322 / make_msgid: <random@domain>
+    assert mid.startswith("<") and mid.endswith(">")
+    assert "@ohm.wiggleverse.org>" in mid
+
+
+def test_envelope_message_id_domain_override():
+    msg = build_envelope(**_base_kwargs(msgid_domain="example.test"))
+    assert "@example.test>" in msg["Message-ID"]
+
+
+def test_envelope_message_id_falls_back_to_localhost_if_from_has_no_at():
+    # Defensive: a malformed from_address shouldn't crash the helper.
+    msg = build_envelope(**_base_kwargs(from_address="bare-no-at-sign"))
+    assert "@localhost>" in msg["Message-ID"]
+
+
+# ---------------------------------------------------------------------------
+# Auto-Submitted (RFC 3834)
+# ---------------------------------------------------------------------------
+
+
+def test_envelope_sets_auto_submitted_for_transactional_default():
+    msg = build_envelope(**_base_kwargs())
+    assert msg["Auto-Submitted"] == "auto-generated"
+
+
+def test_envelope_omits_auto_submitted_when_transactional_is_false():
+    msg = build_envelope(**_base_kwargs(is_transactional=False))
+    assert msg["Auto-Submitted"] is None
+
+
+# ---------------------------------------------------------------------------
+# Reply-To
+# ---------------------------------------------------------------------------
+
+
+def test_envelope_sets_reply_to_when_provided():
+    msg = build_envelope(**_base_kwargs(reply_to="ohm@wiggleverse.org"))
+    assert msg["Reply-To"] == "ohm@wiggleverse.org"
+
+
+def test_envelope_omits_reply_to_when_absent():
+    msg = build_envelope(**_base_kwargs())
+    assert msg["Reply-To"] is None
+
+
+# ---------------------------------------------------------------------------
+# List-Unsubscribe (the headers RFC 8058 / Gmail-Yahoo care about)
+# ---------------------------------------------------------------------------
+
+
+def test_envelope_no_list_unsubscribe_when_neither_given():
+    """OTC mail: the recipient explicitly requested the code; no
+    unsubscribe semantics. The header MUST be absent (presence would
+    imply OHM has the recipient on a list, which it doesn't)."""
+    msg = build_envelope(**_base_kwargs())
+    assert msg["List-Unsubscribe"] is None
+    assert msg["List-Unsubscribe-Post"] is None
+
+
+def test_envelope_mailto_only_list_unsubscribe():
+    """Admin invite / per-RFC invite: `mailto:` form only, no URL.
+    The recipient isn't a user yet, so there's no per-user opt-out
+    URL to flip; the operator handles ad-hoc opt-outs manually."""
+    msg = build_envelope(**_base_kwargs(
+        unsubscribe_mailto="ohm@wiggleverse.org?subject=remove",
+    ))
+    assert msg["List-Unsubscribe"] == "<mailto:ohm@wiggleverse.org?subject=remove>"
+    # NO List-Unsubscribe-Post when only a mailto is present — the
+    # one-click semantic requires a URL the MUA can POST to.
+    assert msg["List-Unsubscribe-Post"] is None
+
+
+def test_envelope_full_one_click_list_unsubscribe():
+    """Watcher notification / bundle: `mailto:` + signed-URL +
+    `List-Unsubscribe-Post: List-Unsubscribe=One-Click`. Gmail and
+    Yahoo enforce this for bulk-adjacent mail per RFC 8058."""
+    msg = build_envelope(**_base_kwargs(
+        unsubscribe_mailto="ohm@wiggleverse.org?subject=remove",
+        unsubscribe_url="https://ohm.wiggleverse.org/api/email/unsubscribe?t=abc",
+    ))
+    lu = msg["List-Unsubscribe"]
+    assert "<mailto:ohm@wiggleverse.org?subject=remove>" in lu
+    assert "<https://ohm.wiggleverse.org/api/email/unsubscribe?t=abc>" in lu
+    assert msg["List-Unsubscribe-Post"] == "List-Unsubscribe=One-Click"
+
+
+def test_envelope_url_only_list_unsubscribe_still_sets_post():
+    msg = build_envelope(**_base_kwargs(
+        unsubscribe_url="https://ohm.wiggleverse.org/api/email/unsubscribe?t=abc",
+    ))
+    assert msg["List-Unsubscribe"] == "<https://ohm.wiggleverse.org/api/email/unsubscribe?t=abc>"
+    assert msg["List-Unsubscribe-Post"] == "List-Unsubscribe=One-Click"
+
+
+# ---------------------------------------------------------------------------
+# Body shape — plain-only vs multipart/alternative
+# ---------------------------------------------------------------------------
+
+
+def test_envelope_plain_only_body_is_text_plain():
+    msg = build_envelope(**_base_kwargs())
+    # No HTML alternative -> single-part text/plain.
+    assert msg.get_content_type() == "text/plain"
+    assert msg.get_content().strip() == "Hello, world."
+
+
+def test_envelope_with_html_is_multipart_alternative():
+    msg = build_envelope(**_base_kwargs(body_html="<p>Hello, <b>world</b>.</p>"))
+    assert msg.get_content_type() == "multipart/alternative"
+    # Two parts: text/plain first (so plain-text clients picking the
+    # first part get the readable text), text/html second.
+    parts = list(msg.iter_parts())
+    assert len(parts) == 2
+    assert parts[0].get_content_type() == "text/plain"
+    assert parts[1].get_content_type() == "text/html"
+    assert "Hello, world." in parts[0].get_content()
+    assert "<b>world</b>" in parts[1].get_content()