webmail-client/backend/tests/outbox/test_draft_sync.py

"""Mirroring local drafts to the IMAP Drafts folder (continue on any client)."""

from __future__ import annotations

import uuid
from collections.abc import AsyncIterator
from dataclasses import dataclass

import pytest_asyncio
from sqlalchemy import delete, select
from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker, create_async_engine
from sqlalchemy.pool import NullPool

from app.config import get_settings
from app.db import session_scope
from app.identity.passwords import hash_password
from app.models import Account, Draft, Mailbox, User
from app.outbox import draft_sync


@dataclass
class Ctx:
    session: AsyncSession
    user_id: uuid.UUID
    account_id: uuid.UUID


@pytest_asyncio.fixture
async def ctx() -> AsyncIterator[Ctx]:
    engine = create_async_engine(get_settings().database_url, poolclass=NullPool)
    sm = async_sessionmaker(engine, expire_on_commit=False)
    session = sm()
    user = User(handle=f"drf{uuid.uuid4().hex[:8]}@test.local", password_hash=hash_password("pw"))
    session.add(user)
    await session.flush()
    account = Account(
        user_id=user.id,
        email="me@example.com",
        display_name="Me",
        imap_config={},
        smtp_config={},
        secret_ct=b"",
        discovery_src="manual",
    )
    session.add(account)
    await session.flush()
    session.add(
        Mailbox(account_id=account.id, user_id=user.id, path="DRAFTS", special_use="drafts")
    )
    await session.commit()
    try:
        yield Ctx(session=session, user_id=user.id, account_id=account.id)
    finally:
        await session.execute(delete(User).where(User.id == user.id))
        await session.commit()
        await session.close()
        await engine.dispose()


class FakeProvider:
    def __init__(self) -> None:
        self.appended: list[tuple[str, frozenset[str]]] = []
        self.deleted: list[tuple[str, list[int]]] = []
        self._uid = 41

    async def append(self, mailbox: str, raw: bytes, flags: frozenset[str]) -> int:
        self.appended.append((mailbox, flags))
        self._uid += 1
        return self._uid

    async def delete_messages(self, mailbox: str, uids: list[int]) -> None:
        self.deleted.append((mailbox, list(uids)))

    async def close(self) -> None:
        return None


async def _make_draft(ctx: Ctx) -> uuid.UUID:
    draft = Draft(
        user_id=ctx.user_id,
        account_id=ctx.account_id,
        kind="new",
        payload={"to": ["bob@example.com"], "subject": "Hi", "html": "<p>hi</p>", "text": ""},
    )
    ctx.session.add(draft)
    await ctx.session.commit()
    return draft.id


async def test_push_draft_appends_with_draft_flag_and_replaces(ctx: Ctx, monkeypatch) -> None:  # type: ignore[no-untyped-def]
    did = await _make_draft(ctx)
    fake = FakeProvider()
    monkeypatch.setattr(draft_sync, "build_provider", lambda _a: fake)

    await draft_sync.push_draft_to_imap_job({}, str(did))

    # appended once to DRAFTS with the \Draft flag; UID recorded on the draft
    assert len(fake.appended) == 1
    assert fake.appended[0][0] == "DRAFTS"
    assert "\\Draft" in fake.appended[0][1]
    assert fake.deleted == []  # nothing to replace yet
    async with session_scope() as s:
        assert (await s.get(Draft, did)).imap_uid == 42  # type: ignore[union-attr]

    # A second push (edit) appends a new copy and expunges the previous UID.
    await draft_sync.push_draft_to_imap_job({}, str(did))
    assert len(fake.appended) == 2
    assert fake.deleted == [("DRAFTS", [42])]
    async with session_scope() as s:
        assert (await s.get(Draft, did)).imap_uid == 43  # type: ignore[union-attr]


async def test_draft_messages_are_not_threaded(ctx: Ctx) -> None:
    from datetime import UTC, datetime
    from email.message import EmailMessage

    from app.indexer.indexer import persist_message
    from app.providers.base import RemoteMessage

    m = EmailMessage()
    m["Subject"] = "A draft reply"
    m["From"] = "me@example.com"
    m["To"] = "bob@example.com"
    m["Message-ID"] = "<d1@x.com>"
    m["In-Reply-To"] = "<orig@x.com>"  # would normally thread it
    m["Date"] = "Mon, 09 Mar 2026 08:36:37 +0100"
    m.set_content("body")

    drafts_mb = await ctx.session.scalar(
        select(Mailbox).where(
            Mailbox.account_id == ctx.account_id, Mailbox.special_use == "drafts"
        )
    )
    assert drafts_mb is not None
    remote = RemoteMessage(
        uid=71, raw=m.as_bytes(), flags=frozenset({"\\Draft"}), internal_date=datetime.now(UTC)
    )
    result = await persist_message(
        ctx.session,
        user_id=ctx.user_id,
        account_id=ctx.account_id,
        mailbox_id=drafts_mb.id,
        mailbox_special_use="drafts",
        remote=remote,
    )
    await ctx.session.commit()
    assert result is not None
    assert result.message.thread_id is None  # drafts stay out of conversations


async def test_remove_imap_draft_expunges(ctx: Ctx, monkeypatch) -> None:  # type: ignore[no-untyped-def]
    fake = FakeProvider()
    monkeypatch.setattr(draft_sync, "build_provider", lambda _a: fake)
    await draft_sync.remove_imap_draft_job({}, str(ctx.account_id), 7)
    assert fake.deleted == [("DRAFTS", [7])]


async def test_no_drafts_mailbox_creates_one(ctx: Ctx, monkeypatch) -> None:  # type: ignore[no-untyped-def]
    # Drop the drafts mailbox so the job has to create it.
    await ctx.session.execute(
        delete(Mailbox).where(Mailbox.account_id == ctx.account_id, Mailbox.special_use == "drafts")
    )
    await ctx.session.commit()
    did = await _make_draft(ctx)

    created: list[str] = []

    class CreatingProvider(FakeProvider):
        async def create_mailbox(self, path: str) -> None:
            created.append(path)

        async def list_mailboxes(self):  # type: ignore[no-untyped-def]
            from app.providers.base import RemoteMailbox

            return [RemoteMailbox(path="Drafts", special_use="drafts", uidvalidity=1)]

    fake = CreatingProvider()
    monkeypatch.setattr(draft_sync, "build_provider", lambda _a: fake)

    await draft_sync.push_draft_to_imap_job({}, str(did))
    assert created == ["Drafts"]
    async with session_scope() as s:
        mb = await s.scalar(
            select(Mailbox).where(
                Mailbox.account_id == ctx.account_id, Mailbox.special_use == "drafts"
            )
        )
        assert mb is not None and mb.path == "Drafts"