odysseus/tests/test_email_owner_scope.py

import sqlite3
from contextlib import contextmanager
from datetime import datetime, timedelta, timezone
from types import SimpleNamespace

import pytest


def _route_endpoint(router, path: str, method: str):
    method = method.upper()
    for route in router.routes:
        if route.path == path and method in getattr(route, "methods", set()):
            return route.endpoint
    raise AssertionError(f"route not found: {method} {path}")


def test_email_tag_clause_excludes_legacy_owner_rows_for_authenticated_owner(monkeypatch):
    import routes.email_routes as email_routes

    monkeypatch.setattr(
        email_routes,
        "_email_tag_owner_aliases",
        lambda account_id, owner="": ["alice", "alice@example.com"],
    )

    clause, params = email_routes._email_tag_owner_clause("acct-alice", "alice")

    assert clause == "owner IN (?,?)"
    assert params == ["alice", "alice@example.com"]
    assert "owner IS NULL" not in clause


def test_email_tag_clause_keeps_legacy_rows_for_single_user_mode(monkeypatch):
    import routes.email_routes as email_routes

    monkeypatch.setattr(
        email_routes,
        "_email_tag_owner_aliases",
        lambda account_id, owner="": [""],
    )

    clause, params = email_routes._email_tag_owner_clause(None, "")

    assert clause == "(owner IN (?) OR owner IS NULL)"
    assert params == [""]


def test_email_ai_cache_tables_are_owner_scoped_and_migrate_legacy_rows(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        CREATE TABLE email_summaries (
            message_id TEXT PRIMARY KEY,
            uid TEXT,
            folder TEXT,
            subject TEXT,
            sender TEXT,
            summary TEXT NOT NULL,
            model_used TEXT,
            created_at TEXT NOT NULL
        )
        """
    )
    conn.execute(
        """
        INSERT INTO email_summaries
        (message_id, uid, folder, subject, sender, summary, model_used, created_at)
        VALUES ('<shared@example.com>', '1', 'INBOX', 'Subject', 'a@example.com', 'legacy', 'm', '2026-01-01')
        """
    )
    conn.commit()
    conn.close()

    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    try:
        for table in (
            "email_summaries",
            "email_ai_replies",
            "email_calendar_extractions",
            "email_urgency_alerts",
        ):
            info = conn.execute(f"PRAGMA table_info({table})").fetchall()
            pk_cols = [r[1] for r in sorted((r for r in info if r[5]), key=lambda r: r[5])]
            assert pk_cols == ["message_id", "owner"]
        assert conn.execute(
            "SELECT owner, summary FROM email_summaries WHERE message_id=?",
            ("<shared@example.com>",),
        ).fetchone() == ("", "legacy")

        conn.execute(
            """
            INSERT INTO email_summaries
            (message_id, owner, uid, folder, subject, sender, summary, model_used, created_at)
            VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?)
            """,
            ("<shared@example.com>", "alice", "2", "INBOX", "Subject", "a@example.com", "alice", "m", "2026-01-02"),
        )
        conn.execute(
            """
            INSERT INTO email_summaries
            (message_id, owner, uid, folder, subject, sender, summary, model_used, created_at)
            VALUES (?, ?, ?, ?, ?, ?, ?, ?, ?)
            """,
            ("<shared@example.com>", "bob", "3", "INBOX", "Subject", "a@example.com", "bob", "m", "2026-01-03"),
        )
        rows = conn.execute(
            "SELECT owner, summary FROM email_summaries WHERE message_id=? ORDER BY owner",
            ("<shared@example.com>",),
        ).fetchall()
        assert rows == [("", "legacy"), ("alice", "alice"), ("bob", "bob")]
    finally:
        conn.close()


def test_sender_signature_cache_is_owner_scoped_and_migrates_legacy_rows(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        CREATE TABLE sender_signatures (
            from_address TEXT PRIMARY KEY,
            signature_text TEXT,
            sample_count INTEGER,
            last_built_at TEXT NOT NULL,
            model_used TEXT,
            source TEXT
        )
        """
    )
    conn.execute(
        """
        INSERT INTO sender_signatures
        (from_address, signature_text, sample_count, last_built_at, model_used, source)
        VALUES ('writer@example.com', 'legacy sig', 3, '2026-01-01', 'm', 'llm')
        """
    )
    conn.commit()
    conn.close()

    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    try:
        info = conn.execute("PRAGMA table_info(sender_signatures)").fetchall()
        pk_cols = [r[1] for r in sorted((r for r in info if r[5]), key=lambda r: r[5])]
        assert pk_cols == ["from_address", "owner"]
        assert conn.execute(
            "SELECT owner, signature_text FROM sender_signatures WHERE from_address=?",
            ("writer@example.com",),
        ).fetchone() == ("", "legacy sig")
        conn.execute(
            """
            INSERT INTO sender_signatures
            (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
            VALUES (?, ?, ?, ?, ?, ?, ?)
            """,
            ("writer@example.com", "alice", "alice sig", 3, "2026-01-02", "m", "llm"),
        )
        conn.execute(
            """
            INSERT INTO sender_signatures
            (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
            VALUES (?, ?, ?, ?, ?, ?, ?)
            """,
            ("writer@example.com", "bob", "bob sig", 3, "2026-01-03", "m", "llm"),
        )
        rows = conn.execute(
            "SELECT owner, signature_text FROM sender_signatures WHERE from_address=? ORDER BY owner",
            ("writer@example.com",),
        ).fetchall()
        assert rows == [("", "legacy sig"), ("alice", "alice sig"), ("bob", "bob sig")]
    finally:
        conn.close()


@pytest.mark.asyncio
async def test_ai_reply_cache_lookup_is_owner_scoped(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers
    import routes.email_routes as email_routes

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)
    monkeypatch.setattr(email_routes, "SCHEDULED_DB", db_path)
    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        INSERT INTO email_ai_replies
        (message_id, owner, uid, folder, reply, model_used, created_at)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("<shared@example.com>", "alice", "1", "INBOX", "alice private draft", "m-a", "2026-01-01"),
    )
    conn.execute(
        """
        INSERT INTO email_ai_replies
        (message_id, owner, uid, folder, reply, model_used, created_at)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("<shared@example.com>", "bob", "2", "INBOX", "bob private draft", "m-b", "2026-01-02"),
    )
    conn.commit()
    conn.close()

    router = email_routes.setup_email_routes()
    ai_reply = _route_endpoint(router, "/api/email/ai-reply", "POST")

    result = await ai_reply(
        {
            "to": "sender@example.com",
            "subject": "Subject",
            "original_body": "Body",
            "message_id": "<shared@example.com>",
        },
        owner="bob",
    )

    assert result["success"] is True
    assert result["cached"] is True
    assert result["reply"] == "bob private draft"
    assert result["model_used"] == "m-b"


@pytest.mark.asyncio
async def test_sender_signature_read_lookup_is_owner_scoped(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers
    import routes.email_routes as email_routes

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)
    monkeypatch.setattr(email_routes, "SCHEDULED_DB", db_path)
    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        INSERT INTO sender_signatures
        (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("writer@example.com", "alice", "alice private sig", 3, "2026-01-01", "m-a", "llm"),
    )
    conn.execute(
        """
        INSERT INTO sender_signatures
        (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("writer@example.com", "bob", "bob private sig", 3, "2026-01-02", "m-b", "llm"),
    )
    conn.commit()
    conn.close()

    raw = (
        b"From: Writer <writer@example.com>\r\n"
        b"To: Bob <bob@example.com>\r\n"
        b"Subject: Hello\r\n"
        b"Message-ID: <shared@example.com>\r\n"
        b"Date: Tue, 01 Jan 2026 12:00:00 +0000\r\n"
        b"Content-Type: text/plain; charset=utf-8\r\n"
        b"\r\n"
        b"Body"
    )

    class FakeImap:
        def select(self, *_args, **_kwargs):
            return "OK", []

        def uid(self, command, _uid, query):
            assert command == "FETCH"
            assert query == "(BODY.PEEK[])"
            return "OK", [(b"1 (UID 1 BODY[])", raw)]

    @contextmanager
    def fake_imap(_account_id=None, owner=""):
        assert owner == "bob"
        yield FakeImap()

    monkeypatch.setattr(email_routes, "_imap", fake_imap)
    router = email_routes.setup_email_routes()
    read_email = _route_endpoint(router, "/api/email/read/{uid}", "GET")

    result = await read_email("1", folder="INBOX", account_id=None, owner="bob", mark_seen=False)

    assert result["sender_signature"] == "bob private sig"


@pytest.mark.asyncio
async def test_sender_signature_clear_cache_keeps_other_owner_rows(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers
    import routes.task_routes as task_routes

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)
    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        INSERT INTO sender_signatures
        (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("writer@example.com", "alice", "alice private sig", 3, "2026-01-01", "m-a", "llm"),
    )
    conn.execute(
        """
        INSERT INTO sender_signatures
        (from_address, owner, signature_text, sample_count, last_built_at, model_used, source)
        VALUES (?, ?, ?, ?, ?, ?, ?)
        """,
        ("writer@example.com", "bob", "bob private sig", 3, "2026-01-02", "m-b", "llm"),
    )
    conn.commit()
    conn.close()

    class FakeQuery:
        def filter(self, *_args):
            return self

        def first(self):
            return SimpleNamespace(
                id="task-1",
                owner="alice",
                action="learn_sender_signatures",
            )

    class FakeDb:
        def query(self, _model):
            return FakeQuery()

        def close(self):
            pass

    monkeypatch.setattr(task_routes, "SessionLocal", lambda: FakeDb())
    monkeypatch.setattr(task_routes, "get_current_user", lambda _request: "alice")

    router = task_routes.setup_task_routes(task_scheduler=SimpleNamespace(pop_notifications=lambda owner: []))
    clear_cache = _route_endpoint(router, "/api/tasks/{task_id}/clear-cache", "POST")

    result = await clear_cache(SimpleNamespace(), "task-1")

    assert result["cleared"]["sender_signatures"] == 1
    conn = sqlite3.connect(db_path)
    try:
        rows = conn.execute(
            "SELECT owner, signature_text FROM sender_signatures ORDER BY owner",
        ).fetchall()
    finally:
        conn.close()
    assert rows == [("bob", "bob private sig")]


@pytest.mark.asyncio
async def test_scheduled_email_routes_are_owner_scoped(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers
    import routes.email_routes as email_routes

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)
    monkeypatch.setattr(email_routes, "SCHEDULED_DB", db_path)
    email_helpers._init_scheduled_db()

    router = email_routes.setup_email_routes()
    schedule_email = _route_endpoint(router, "/api/email/schedule", "POST")
    list_scheduled = _route_endpoint(router, "/api/email/scheduled", "GET")
    cancel_scheduled = _route_endpoint(router, "/api/email/scheduled/{sid}", "DELETE")

    send_at = (datetime.now(timezone.utc) + timedelta(days=1)).isoformat()
    alice = await schedule_email(
        {"to": "a@example.com", "body": "alice body", "send_at": send_at},
        owner="alice",
    )
    bob = await schedule_email(
        {"to": "b@example.com", "body": "bob body", "send_at": send_at},
        owner="bob",
    )

    assert alice["success"] is True
    assert bob["success"] is True

    alice_rows = await list_scheduled(owner="alice")
    bob_rows = await list_scheduled(owner="bob")

    assert [row["id"] for row in alice_rows["scheduled"]] == [alice["id"]]
    assert [row["id"] for row in bob_rows["scheduled"]] == [bob["id"]]

    await cancel_scheduled(bob["id"], owner="alice")
    bob_rows = await list_scheduled(owner="bob")
    assert [row["id"] for row in bob_rows["scheduled"]] == [bob["id"]]

    await cancel_scheduled(alice["id"], owner="alice")
    alice_rows = await list_scheduled(owner="alice")
    assert alice_rows["scheduled"] == []


def test_scheduled_poller_resolves_config_with_row_owner(tmp_path, monkeypatch):
    import routes.email_helpers as email_helpers
    import routes.email_pollers as email_pollers

    db_path = tmp_path / "scheduled_emails.db"
    monkeypatch.setattr(email_helpers, "SCHEDULED_DB", db_path)
    monkeypatch.setattr(email_pollers, "SCHEDULED_DB", db_path)
    email_helpers._init_scheduled_db()

    conn = sqlite3.connect(db_path)
    conn.execute(
        """
        INSERT INTO scheduled_emails
        (id, to_addr, subject, body, attachments, send_at, created_at, status, account_id, owner)
        VALUES (?, ?, ?, ?, ?, ?, ?, 'pending', ?, ?)
        """,
        (
            "sched-1",
            "recipient@example.com",
            "Subject",
            "Body",
            "[]",
            "2000-01-01T00:00:00",
            "1999-12-31T00:00:00",
            "acct-alice",
            "alice",
        ),
    )
    conn.commit()
    conn.close()

    calls = []

    def fake_get_email_config(account_id=None, owner=""):
        calls.append(("config", account_id, owner))
        return {
            "from_address": "alice@example.com",
            "smtp_host": "smtp.example.com",
            "smtp_user": "alice@example.com",
            "smtp_password": "secret",
        }

    class FakeImap:
        def __init__(self, account_id=None, owner=""):
            calls.append(("imap", account_id, owner))

        def __enter__(self):
            return self

        def __exit__(self, exc_type, exc, tb):
            return False

        def append(self, folder, flags, date_time, message):
            calls.append(("append", folder))

    monkeypatch.setattr(email_pollers, "_get_email_config", fake_get_email_config)
    monkeypatch.setattr(email_pollers, "_send_smtp_message", lambda *args, **kwargs: calls.append(("send", args[1], args[2])))
    monkeypatch.setattr(email_pollers, "_imap", FakeImap)
    monkeypatch.setattr(email_pollers, "_detect_sent_folder", lambda imap: "Sent")
    monkeypatch.setattr(email_pollers, "_cleanup_compose_uploads", lambda attachments: calls.append(("cleanup", attachments)))

    result = email_pollers._scheduled_poll_once()

    assert result == {"sent": ["sched-1"], "failed": []}
    assert ("config", "acct-alice", "alice") in calls
    assert ("imap", "acct-alice", "alice") in calls