webmail-client/backend/tests/plugins/test_calendar_invitations.py

"""Calendar plugin: invitations received by email (iMIP) — the reading-pane card
and Yes / No / Maybe, through the real HTTP surface.

A Gmail-style invitation (text/calendar METHOD:REQUEST + an invite.ics file) is
stored as a real message; answering must put the event in the calendar (or take
it out) and send the organizer an iTIP REPLY. Outgoing mail is captured, not sent.
"""

from __future__ import annotations

import uuid
from collections.abc import AsyncIterator
from dataclasses import dataclass, field
from datetime import UTC, datetime
from email.message import EmailMessage

import httpx
import pytest_asyncio
from httpx import ASGITransport
from sqlalchemy import delete, text
from sqlalchemy.ext.asyncio import async_sessionmaker, create_async_engine
from sqlalchemy.pool import NullPool

from app.config import get_settings
from app.identity.passwords import hash_password
from app.identity.sessions import create_session
from app.indexer.indexer import persist_message
from app.indexer.mime import parse_message
from app.main import create_app
from app.models import Account, Mailbox, User
from app.plugins import mail as plugin_mail
from app.providers.base import RemoteMessage

CAL = "/api/plugins/calendar"
ME = "me@example.com"
ORGANIZER = "boss@example.org"


def _ics(method: str = "REQUEST", attendees: tuple[str, ...] = (ME,), seq: int = 0) -> str:
    people = "".join(
        f"ATTENDEE;CN=Guest;PARTSTAT=NEEDS-ACTION;RSVP=TRUE:mailto:{a}\r\n" for a in attendees
    )
    return (
        "BEGIN:VCALENDAR\r\nPRODID:-//Google Inc//Google Calendar 70.9054//EN\r\n"
        f"VERSION:2.0\r\nMETHOD:{method}\r\n"
        "BEGIN:VEVENT\r\n"
        "DTSTART;TZID=Europe/Warsaw:20261007T133000\r\n"
        "DTEND;TZID=Europe/Warsaw:20261007T143000\r\n"
        "DTSTAMP:20261006T183413Z\r\n"
        f"ORGANIZER;CN=The Boss:mailto:{ORGANIZER}\r\n"
        "UID:test-invite-1@google.com\r\n"
        f"{people}"
        "X-GOOGLE-CONFERENCE:https://meet.google.com/abc-defg-hij\r\n"
        "LOCATION:Gliwice\r\n"
        f"SEQUENCE:{seq}\r\nSTATUS:{'CANCELLED' if method == 'CANCEL' else 'CONFIRMED'}\r\n"
        "SUMMARY:Maintenance Renewal\r\nEND:VEVENT\r\nEND:VCALENDAR\r\n"
    )


def _email(ics: str, method: str) -> bytes:
    m = EmailMessage()
    m["Subject"] = "Invitation: Maintenance Renewal"
    m["From"] = f"The Boss <{ORGANIZER}>"
    m["To"] = ME
    m["Message-ID"] = f"<{uuid.uuid4()}@example.org>"
    m.set_content("You have been invited.")
    m.add_alternative("<p>You have been invited.</p>", subtype="html")
    m.add_alternative(ics, subtype="calendar", params={"method": method})
    m.make_mixed()
    m.add_attachment(ics.encode(), maintype="application", subtype="ics", filename="invite.ics")
    return m.as_bytes()


@dataclass
class Ctx:
    user_id: uuid.UUID
    client: httpx.AsyncClient
    sm: async_sessionmaker  # type: ignore[type-arg]
    account_id: uuid.UUID
    mailbox_id: uuid.UUID
    sent: list[dict[str, object]] = field(default_factory=list)
    uid: int = 0

    async def message(self, raw: bytes) -> str:
        self.uid += 1
        async with self.sm() as s:
            result = await persist_message(
                s,
                user_id=self.user_id,
                account_id=self.account_id,
                mailbox_id=self.mailbox_id,
                mailbox_special_use="inbox",
                remote=RemoteMessage(
                    uid=self.uid, raw=raw, flags=frozenset(), internal_date=datetime.now(UTC)
                ),
            )
            await s.commit()
        assert result is not None
        return str(result.message.id)


@pytest_asyncio.fixture
async def ctx(monkeypatch) -> AsyncIterator[Ctx]:  # type: ignore[no-untyped-def]
    engine = create_async_engine(get_settings().database_url, poolclass=NullPool)
    sm = async_sessionmaker(engine, expire_on_commit=False)
    async with sm() as s:
        user = User(
            handle=f"inv{uuid.uuid4().hex[:8]}@test.local", password_hash=hash_password("pw")
        )
        s.add(user)
        await s.flush()
        account = Account(
            user_id=user.id,
            email=ME,
            display_name="Me Myself",
            imap_config={"host": "imap.example.com", "port": 993, "tls": "ssl"},
            smtp_config={"host": "smtp.example.com", "port": 465, "tls": "ssl"},
            secret_ct=b"",
            discovery_src="manual",
            state="live",
        )
        s.add(account)
        await s.flush()
        inbox = Mailbox(account_id=account.id, user_id=user.id, path="INBOX", special_use="inbox")
        s.add(inbox)
        await s.commit()
        ids = (user.id, account.id, inbox.id)
    token = await create_session(ids[0], "pytest")
    client = httpx.AsyncClient(
        transport=ASGITransport(app=create_app()),
        base_url="http://testserver",
        cookies={"session": token, "csrf": "csrf"},
        headers={"X-CSRF": "csrf"},
    )
    c = Ctx(user_id=ids[0], client=client, sm=sm, account_id=ids[1], mailbox_id=ids[2])

    async def fake_send(self, user_id, **kw):  # type: ignore[no-untyped-def]
        c.sent.append(kw)

    monkeypatch.setattr(plugin_mail.PluginMail, "send", fake_send)
    try:
        yield c
    finally:
        await client.aclose()
        async with sm() as s:
            await s.execute(
                text("DELETE FROM plg_calendar_calendars WHERE user_id = :u"), {"u": str(ids[0])}
            )
            await s.execute(delete(User).where(User.id == ids[0]))
            await s.commit()
        await engine.dispose()


async def _policy(c: Ctx, policy: str, **more: object) -> None:
    """Settings → Calendars → Invitations."""
    r = await c.client.patch("/api/settings", json={"invitation_policy": policy, **more})
    assert r.status_code == 200 and r.json()["invitation_policy"] == policy


async def _arrives(c: Ctx, raw: bytes) -> str:
    """A message stored and announced, as the sync engine does (message.new)."""
    from webmail_plugin_calendar.hook import on_message_new

    mid = await c.message(raw)
    await on_message_new({"user_id": str(c.user_id), "message_id": mid})
    return mid


async def _calendar_events(c: Ctx) -> list[dict[str, object]]:
    r = await c.client.get(
        f"{CAL}/events", params={"start": "2026-10-07T00:00:00Z", "end": "2026-10-08T00:00:00Z"}
    )
    return r.json()["events"]


async def test_invitation_card_and_answers(ctx: Ctx) -> None:
    mid = await ctx.message(_email(_ics(), "REQUEST"))

    # Something already in the calendar at that time: a conflict.
    cal_id = (await ctx.client.get(f"{CAL}/calendars")).json()[0]["id"]
    await ctx.client.post(
        f"{CAL}/events",
        json={
            "calendar_id": cal_id,
            "summary": "Design review",
            "dtstart": "2026-10-07T11:00:00Z",  # 13:00 in Warsaw
            "dtend": "2026-10-07T12:00:00Z",
        },
    )

    card = (await ctx.client.get(f"{CAL}/invitations/{mid}")).json()
    assert card["method"] == "REQUEST" and card["summary"] == "Maintenance Renewal"
    assert card["start"] == "2026-10-07T13:30:00+02:00" and card["tz"] == "Europe/Warsaw"
    assert card["organizer"] == {"email": ORGANIZER, "name": "The Boss"}
    assert card["location"] == "Gliwice"
    assert card["conference_url"] == "https://meet.google.com/abc-defg-hij"
    assert card["me"]["email"] == ME and card["response"] == "needs-action"
    assert card["in_calendar"] is None
    assert [c["summary"] for c in card["conflicts"]] == ["Design review"]

    # Yes: in the calendar, and the organizer gets an iTIP REPLY.
    r = await ctx.client.post(f"{CAL}/invitations/{mid}/respond", json={"response": "accepted"})
    assert r.status_code == 200
    card = r.json()
    assert card["response"] == "accepted" and card["in_calendar"]["calendar"] == "Personal"
    assert card["reply_sent"] is True
    reply = ctx.sent[-1]
    assert reply["to"] == [ORGANIZER] and reply["from_email"] == ME
    assert reply["ics_method"] == "REPLY" and reply["subject"] == "Accepted: Maintenance Renewal"
    ics = str(reply["ics"])
    assert "METHOD:REPLY" in ics and "UID:test-invite-1@google.com" in ics
    assert "PARTSTAT=ACCEPTED" in ics and f"mailto:{ME}" in ics
    events = [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    assert len(events) == 1 and events[0]["my_partstat"] == "accepted"

    # Maybe: the same event, answer updated.
    r = await ctx.client.post(f"{CAL}/invitations/{mid}/respond", json={"response": "tentative"})
    assert r.json()["response"] == "tentative" and "PARTSTAT=TENTATIVE" in str(ctx.sent[-1]["ics"])
    events = [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    assert len(events) == 1 and events[0]["my_partstat"] == "tentative"

    # No: out of the calendar — and still shown as the answer given.
    r = await ctx.client.post(f"{CAL}/invitations/{mid}/respond", json={"response": "declined"})
    assert r.json()["in_calendar"] is None and "PARTSTAT=DECLINED" in str(ctx.sent[-1]["ics"])
    assert r.json()["response"] == "declined"
    assert (await ctx.client.get(f"{CAL}/invitations/{mid}")).json()["response"] == "declined"
    assert not [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]

    # Changing one's mind back to Yes: in the calendar again, "No" forgotten.
    r = await ctx.client.post(f"{CAL}/invitations/{mid}/respond", json={"response": "accepted"})
    assert r.json()["response"] == "accepted" and r.json()["in_calendar"] is not None


async def test_organizers_cancellation_is_applied_on_arrival(ctx: Ctx) -> None:
    from webmail_plugin_calendar.hook import on_message_new

    invite = await ctx.message(_email(_ics(), "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "accepted"})
    assert [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]

    # The organizer calls it off: gone as the email arrives, nothing to click.
    cancel = await ctx.message(_email(_ics("CANCEL", seq=1), "CANCEL"))
    await on_message_new({"user_id": str(ctx.user_id), "message_id": cancel})
    assert not [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    card = (await ctx.client.get(f"{CAL}/invitations/{cancel}")).json()
    assert card["method"] == "CANCEL" and card["cancellation"] == "removed"
    # A cancellation cannot be answered.
    no = await ctx.client.post(f"{CAL}/invitations/{cancel}/respond", json={"response": "accepted"})
    assert no.status_code == 400


async def test_older_cancellation_is_applied_when_opened(ctx: Ctx) -> None:
    invite = await ctx.message(_email(_ics(), "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "tentative"})
    cancel = await ctx.message(_email(_ics("CANCEL", seq=1), "CANCEL"))  # no hook ran
    card = (await ctx.client.get(f"{CAL}/invitations/{cancel}")).json()
    assert card["cancellation"] == "removed"
    assert not [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]


async def test_cancellation_not_from_the_organizer_is_ignored(ctx: Ctx) -> None:
    invite = await ctx.message(_email(_ics(), "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "accepted"})
    forged = _ics("CANCEL", seq=1).replace(f"mailto:{ORGANIZER}", "mailto:prankster@example.com")
    cancel = await ctx.message(_email(forged, "CANCEL"))
    card = (await ctx.client.get(f"{CAL}/invitations/{cancel}")).json()
    assert card["cancellation"] == "not_organizer"
    assert [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]


async def test_cancelled_occurrence_of_a_series(ctx: Ctx) -> None:
    weekly = _ics().replace("SEQUENCE:0", "RRULE:FREQ=WEEKLY\r\nSEQUENCE:0")
    invite = await ctx.message(_email(weekly, "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "accepted"})
    one = _ics("CANCEL", seq=1).replace(
        "SEQUENCE:1", "RECURRENCE-ID;TZID=Europe/Warsaw:20261014T133000\r\nSEQUENCE:1"
    )
    cancel = await ctx.message(_email(one, "CANCEL"))
    assert (await ctx.client.get(f"{CAL}/invitations/{cancel}")).json()["cancellation"] == "removed"
    r = await ctx.client.get(
        f"{CAL}/events", params={"start": "2026-10-06T00:00:00Z", "end": "2026-10-22T00:00:00Z"}
    )
    days = sorted(
        e["start"][:10] for e in r.json()["events"] if e["summary"] == "Maintenance Renewal"
    )
    assert days == ["2026-10-07", "2026-10-21"]  # 14 Oct is gone, the rest stays


async def test_not_invited_or_not_an_invitation(ctx: Ctx) -> None:
    other = await ctx.message(_email(_ics(attendees=("someone@else.com",)), "REQUEST"))
    card = (await ctx.client.get(f"{CAL}/invitations/{other}")).json()
    assert card["me"] is None  # forwarded to the user, say: nothing to answer
    r = await ctx.client.post(f"{CAL}/invitations/{other}/respond", json={"response": "accepted"})
    assert r.status_code == 400

    plain = EmailMessage()
    plain["Subject"], plain["From"], plain["To"] = "Hello", ORGANIZER, ME
    plain.set_content("Just a note.")
    mid = await ctx.message(plain.as_bytes())
    assert (await ctx.client.get(f"{CAL}/invitations/{mid}")).status_code == 404


def test_outlook_style_invitation_is_kept_as_a_file() -> None:
    # Outlook often sends the calendar only as the text/calendar alternative:
    # the indexer keeps it as invite.ics, so the card has something to find.
    m = EmailMessage()
    m["Subject"], m["From"], m["To"] = "Meeting", ORGANIZER, ME
    m.set_content("plain")
    m.add_alternative(_ics(), subtype="calendar", params={"method": "REQUEST"})
    files = parse_message(m.as_bytes()).attachments
    assert [(a.filename, a.mime_type) for a in files] == [("invite.ics", "text/calendar")]


# --- deleting an event with guests: tell them (iTIP CANCEL) -----------------------


async def _my_event(ctx: Ctx, **extra: object) -> str:
    cal_id = (await ctx.client.get(f"{CAL}/calendars")).json()[0]["id"]
    body = {
        "calendar_id": cal_id,
        "summary": "Planning",
        "dtstart": "2026-11-02T09:00:00Z",
        "dtend": "2026-11-02T10:00:00Z",
        "tz": "Europe/Warsaw",
        "organizer": {"email": ME, "name": "Me Myself"},
        "attendees": [{"email": "guest@example.net", "name": "Guest"}, {"email": ME, "name": ""}],
        **extra,
    }
    r = await ctx.client.post(f"{CAL}/events", json=body)
    assert r.status_code == 200
    ctx.sent.clear()  # forget the invitations
    return str(r.json()["id"])


async def test_delete_and_tell_the_guests(ctx: Ctx) -> None:
    event_id = await _my_event(ctx)
    r = await ctx.client.delete(f"{CAL}/events/{event_id}", params={"notify": "1"})
    assert r.json() == {"status": "ok", "notified": 1}
    mail = ctx.sent[-1]
    assert mail["to"] == ["guest@example.net"] and mail["from_email"] == ME  # not to me
    assert mail["ics_method"] == "CANCEL" and str(mail["subject"]).startswith("Canceled: Planning")
    ics = str(mail["ics"])
    assert "METHOD:CANCEL" in ics and "STATUS:CANCELLED" in ics and "SEQUENCE:1" in ics
    assert "RECURRENCE-ID" not in ics


async def test_delete_quietly(ctx: Ctx) -> None:
    event_id = await _my_event(ctx)
    r = await ctx.client.delete(f"{CAL}/events/{event_id}")
    assert r.json()["notified"] == 0 and ctx.sent == []


async def test_cancel_one_occurrence_or_shorten_the_series(ctx: Ctx) -> None:
    event_id = await _my_event(ctx, rrule="FREQ=WEEKLY")
    # Just 16 Nov: a CANCEL of that occurrence.
    r = await ctx.client.delete(
        f"{CAL}/events/{event_id}",
        params={"scope": "this", "occurrence": "2026-11-16T09:00:00Z", "notify": "1"},
    )
    assert r.json()["notified"] == 1
    ics = str(ctx.sent[-1]["ics"])
    assert "METHOD:CANCEL" in ics and "RECURRENCE-ID" in ics and "20261116T" in ics
    assert "RRULE" not in ics

    # From 30 Nov on: not a cancellation — the series now ends earlier.
    r = await ctx.client.delete(
        f"{CAL}/events/{event_id}",
        params={"scope": "following", "occurrence": "2026-11-30T09:00:00Z", "notify": "1"},
    )
    assert r.json()["notified"] == 1
    mail = ctx.sent[-1]
    ics = str(mail["ics"])
    assert mail.get("ics_method", "REQUEST") == "REQUEST" and "METHOD:REQUEST" in ics
    assert "RRULE:FREQ=WEEKLY;UNTIL=20261130T085959Z" in ics and "SEQUENCE:2" in ics


async def test_someone_elses_event_is_not_cancelled_for_its_guests(ctx: Ctx) -> None:
    event_id = await _my_event(ctx, organizer={"email": "boss@example.org", "name": "Boss"})
    r = await ctx.client.delete(f"{CAL}/events/{event_id}", params={"notify": "1"})
    assert r.json()["notified"] == 0 and ctx.sent == []


# --- Settings → Calendars → Invitations: "When I receive events by email" --------


def _moved(ics: str, start: str, end: str) -> str:
    return ics.replace("20261007T133000", start).replace("20261007T143000", end)


async def test_default_changes_nothing_on_its_own(ctx: Ctx) -> None:
    # Default: "Do not automatically update my calendar".
    settings = (await ctx.client.get("/api/settings")).json()
    assert settings["invitation_policy"] == "none"
    await _arrives(ctx, _email(_ics(), "REQUEST"))
    assert not await _calendar_events(ctx)  # not added

    invite = await ctx.message(_email(_ics(), "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "accepted"})
    moved = await _arrives(
        ctx, _email(_moved(_ics(seq=1), "20261007T150000", "20261007T160000"), "REQUEST")
    )
    events = [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    assert [e["start"] for e in events] == ["2026-10-07T11:30:00+00:00"]  # not moved
    assert (await ctx.client.get(f"{CAL}/invitations/{moved}")).json()["update_pending"] is True

    # The one exception: an organizer's cancellation is applied all the same.
    cancel = await _arrives(ctx, _email(_ics("CANCEL", seq=2), "CANCEL"))
    assert not [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    card = (await ctx.client.get(f"{CAL}/invitations/{cancel}")).json()
    assert card["cancellation"] == "removed"


async def test_only_update_events_already_added(ctx: Ctx) -> None:
    await _policy(ctx, "update_only")
    await _arrives(ctx, _email(_ics(), "REQUEST"))
    assert not await _calendar_events(ctx)  # a new one: not added

    invite = await ctx.message(_email(_ics(), "REQUEST"))
    await ctx.client.post(f"{CAL}/invitations/{invite}/respond", json={"response": "tentative"})
    await _arrives(
        ctx, _email(_moved(_ics(seq=1), "20261007T150000", "20261007T160000"), "REQUEST")
    )
    events = [e for e in await _calendar_events(ctx) if e["summary"] == "Maintenance Renewal"]
    assert [e["start"] for e in events] == ["2026-10-07T13:00:00+00:00"]  # moved to 15:00
    assert events[0]["my_partstat"] == "tentative"  # the user's own answer kept
    await _arrives(ctx, _email(_ics("CANCEL", seq=2), "CANCEL"))
    assert not await _calendar_events(ctx)


async def test_add_new_events_from_anyone_or_contacts(ctx: Ctx) -> None:
    await _policy(ctx, "add_update", invitation_from="contacts")
    await _arrives(ctx, _email(_ics(), "REQUEST"))
    assert not await _calendar_events(ctx)  # the organizer is not a contact

    await _policy(ctx, "add_update", invitation_from="anyone")
    mid = await _arrives(ctx, _email(_ics(), "REQUEST"))
    events = await _calendar_events(ctx)
    assert [(e["summary"], e["my_partstat"]) for e in events] == [
        ("Maintenance Renewal", "needs-action")  # added, not answered for the user
    ]
    card = (await ctx.client.get(f"{CAL}/invitations/{mid}")).json()
    assert card["in_calendar"] is not None and card["response"] == "needs-action"
    assert ctx.sent == []  # nobody was told anything


async def test_mark_read_and_file(ctx: Ctx, monkeypatch) -> None:  # type: ignore[no-untyped-def]
    from app import queue as app_queue
    from app.models import Mailbox, Message

    jobs: list[tuple[object, ...]] = []

    class FakePool:
        async def enqueue_job(self, *args: object, **kwargs: object) -> None:
            jobs.append(args)

    async def fake_pool() -> FakePool:
        return FakePool()

    monkeypatch.setattr(app_queue, "get_arq_pool", fake_pool)
    async with ctx.sm() as s:
        s.add(
            Mailbox(
                account_id=ctx.account_id,
                user_id=ctx.user_id,
                path="Archive",
                special_use="archive",
            )
        )
        await s.commit()
    await _policy(ctx, "add_update", invitation_from="anyone", invitation_file=True)
    mid = await _arrives(ctx, _email(_ics(), "REQUEST"))
    async with ctx.sm() as s:
        msg = await s.get(Message, uuid.UUID(mid))
        assert msg is not None and "\\Seen" in msg.flags
        box = await s.get(Mailbox, msg.mailbox_id)
        assert box is not None and box.special_use == "archive"
    assert [j[0] for j in jobs] == ["push_flags_job", "move_job"]