Add per-room opt-in email notifications on mention (#67)

Lets a member subscribe to email when they're @mentioned in a room while offline, alongside #66's always-on DM email. Debounced the same way #66 is (one email per unread burst, not one per mention), and deliberately scoped to regular rooms only -- DMs already have #66's automatic offline email with no separate toggle needed. Co-Authored-By: Claude Sonnet 5 <noreply@anthropic.com>
2026-08-28 19:45:04 -06:00
parent 3dabf0022c
commit 250bb862f6
10 changed files with 441 additions and 6 deletions
@@ -0,0 +1,225 @@
+import uuid
+
+from app.models import SmtpSettings
+from app.schemas.user import UserCreate
+from app.services.auth_service import register_user
+
+
+def _unique(prefix: str) -> str:
+    return f"{prefix}-{uuid.uuid4().hex[:8]}"
+
+
+def _fake_smtp(monkeypatch):
+    calls = []
+
+    async def fake_send(message, **kwargs):
+        calls.append({"message": message, **kwargs})
+
+    monkeypatch.setattr("app.services.email_service.aiosmtplib.send", fake_send)
+
+    # See test_dm_email_notifications.py's identical helper for why this
+    # monkeypatches get_smtp_settings directly instead of configuring a real
+    # row through the admin endpoint.
+    fake_settings = SmtpSettings(
+        host="smtp.example.com",
+        port=587,
+        username="bot",
+        password_encrypted=None,
+        from_address="noreply@example.com",
+        use_tls=True,
+    )
+
+    async def fake_get_smtp_settings(db):
+        return fake_settings
+
+    monkeypatch.setattr("app.services.email_service.get_smtp_settings", fake_get_smtp_settings)
+    return calls
+
+
+def _register_ws(ws_client, username: str) -> dict:
+    async def _seed():
+        async with ws_client.session_factory() as session:
+            await register_user(
+                session,
+                UserCreate(username=username, email=f"{username}@example.com", password="password123"),
+            )
+
+    ws_client.portal.call(_seed)
+    resp = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": "password123"}
+    )
+    assert resp.status_code == 200, resp.text
+    return resp.json()
+
+
+def _send_and_sync(ws, room_id: str, content: str) -> dict:
+    """See test_dm_email_notifications.py's identical helper -- the
+    "message" ack alone proves nothing about whether the email step
+    (awaited afterward in the same handler) has finished; a second,
+    idempotent join's ack only arrives once the whole frame is done."""
+    ws.send_json({"type": "message", "room_id": room_id, "content": content})
+    message = ws.receive_json()
+    ws.send_json({"type": "join", "room_id": room_id})
+    assert ws.receive_json()["type"] == "joined"
+    return message
+
+
+def _subscribe(ws_client, room_id: str, username: str, password: str = "password123") -> None:
+    login = ws_client.post(
+        "/api/auth/login", json={"username_or_email": username, "password": password}
+    )
+    assert login.status_code == 200, login.text
+    resp = ws_client.patch(f"/api/rooms/{room_id}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 204, resp.text
+
+
+def test_room_mention_emails_offline_subscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+    # bob never connects via WS -- genuinely offline.
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], f"hey @{bob['username']}, look at this")
+
+    assert len(calls) == 1
+    email = calls[0]["message"]
+    assert email["To"] == bob["email"]
+    assert f"New mention in #{room['name']}" in email["Subject"]
+    body = email.get_body(preferencelist=("plain",)).get_content()
+    assert alice["username"] in body
+    assert f"/rooms/{room['id']}" in body
+
+
+def test_room_message_without_mention_does_not_email_subscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], "hello room, no mention here")
+
+    assert calls == []
+
+
+def test_room_mention_does_not_email_unsubscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    alice = _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    # bob never opts in -- email_notifications defaults to False.
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], f"hey @{bob['username']}")
+
+    assert calls == []
+
+
+def test_room_mention_does_not_email_online_subscribed_member(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance2.websocket_connect("/ws/chat"):
+        # bob has an open connection -- genuinely online -- even though he
+        # never joins this room's own channel.
+        with instance1.websocket_connect("/ws/chat") as alice_ws:
+            alice_ws.send_json({"type": "join", "room_id": room["id"]})
+            assert alice_ws.receive_json()["type"] == "joined"
+            _send_and_sync(alice_ws, room["id"], f"hey @{bob['username']}")
+
+    assert calls == []
+
+
+def test_room_mention_email_debounced_to_first_unread_then_resets_after_read(ws_client_factory, monkeypatch):
+    calls = _fake_smtp(monkeypatch)
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+    instance2.post(f"/api/rooms/{room['id']}/join")
+    _subscribe(instance2, room["id"], bob["username"])
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+
+        _send_and_sync(alice_ws, room["id"], f"@{bob['username']} first mention")
+        assert len(calls) == 1
+
+        # A second mention while bob still hasn't read the first -- no
+        # second email for the same burst.
+        _send_and_sync(alice_ws, room["id"], f"@{bob['username']} second mention")
+        assert len(calls) == 1
+
+    instance2.post(
+        "/api/auth/login", json={"username_or_email": bob["username"], "password": "password123"}
+    )
+    read_resp = instance2.post(f"/api/rooms/{room['id']}/read")
+    assert read_resp.status_code == 204
+
+    with instance1.websocket_connect("/ws/chat") as alice_ws:
+        alice_ws.send_json({"type": "join", "room_id": room["id"]})
+        assert alice_ws.receive_json()["type"] == "joined"
+        _send_and_sync(alice_ws, room["id"], f"@{bob['username']} third mention")
+
+    assert len(calls) == 2
+
+
+def test_enabling_notifications_rejected_for_dm(ws_client_factory):
+    instance1 = ws_client_factory()
+    instance2 = ws_client_factory()
+
+    _register_ws(instance1, _unique("alice"))
+    bob = _register_ws(instance2, _unique("bob"))
+    dm = instance1.post("/api/rooms/dm", json={"other_user_id": bob["id"]}).json()
+
+    resp = instance1.patch(f"/api/rooms/{dm['id']}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 400
+
+
+def test_notifications_setting_reflected_in_my_rooms(ws_client_factory):
+    instance1 = ws_client_factory()
+    _register_ws(instance1, _unique("alice"))
+    room = instance1.post("/api/rooms", json={"name": _unique("general")}).json()
+
+    rooms = instance1.get("/api/rooms/mine").json()
+    mine = next(r for r in rooms if r["id"] == room["id"])
+    assert mine["email_notifications"] is False
+
+    resp = instance1.patch(f"/api/rooms/{room['id']}/notifications", json={"email_notifications": True})
+    assert resp.status_code == 204
+
+    rooms = instance1.get("/api/rooms/mine").json()
+    mine = next(r for r in rooms if r["id"] == room["id"])
+    assert mine["email_notifications"] is True