python-telegram-bot/tests/test_updater.py

#!/usr/bin/env python
#
# A library that provides a Python interface to the Telegram Bot API
# Copyright (C) 2015-2022
# Leandro Toledo de Souza <devs@python-telegram-bot.org>
#
# This program is free software: you can redistribute it and/or modify
# it under the terms of the GNU Lesser Public License as published by
# the Free Software Foundation, either version 3 of the License, or
# (at your option) any later version.
#
# This program is distributed in the hope that it will be useful,
# but WITHOUT ANY WARRANTY; without even the implied warranty of
# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
# GNU Lesser Public License for more details.
#
# You should have received a copy of the GNU Lesser Public License
# along with this program.  If not, see [http://www.gnu.org/licenses/].
import asyncio
import logging
import os
from collections import defaultdict
from http import HTTPStatus
from pathlib import Path
from random import randrange

import pytest

from telegram import Bot, InlineKeyboardButton, InlineKeyboardMarkup, Update
from telegram._utils.defaultvalue import DEFAULT_NONE
from telegram.error import InvalidToken, RetryAfter, TelegramError, TimedOut
from telegram.ext import ExtBot, InvalidCallbackData, Updater
from telegram.request import HTTPXRequest
from tests.auxil.object_conversions import env_var_2_bool
from tests.conftest import (
    DictBot,
    data_file,
    make_bot,
    make_message,
    make_message_update,
    send_webhook_message,
)

TEST_WITH_OPT_DEPS = env_var_2_bool(os.getenv("TEST_WITH_OPT_DEPS", True))

if TEST_WITH_OPT_DEPS:
    from telegram.ext._utils.webhookhandler import WebhookServer


@pytest.mark.skipif(
    TEST_WITH_OPT_DEPS, reason="Only relevant if the optional dependency is not installed"
)
class TestNoWebhooks:
    async def test_no_webhooks(self, bot):
        with pytest.raises(RuntimeError, match=r"python-telegram-bot\[webhooks\]"):
            async with Updater(bot=bot, update_queue=asyncio.Queue()) as updater:
                await updater.start_webhook()


@pytest.mark.skipif(
    not TEST_WITH_OPT_DEPS,
    reason="Only relevant if the optional dependency is installed",
)
class TestUpdater:
    message_count = 0
    received = None
    attempts = 0
    err_handler_called = None
    cb_handler_called = None
    offset = 0
    test_flag = False

    @pytest.fixture(autouse=True)
    def reset(self):
        self.message_count = 0
        self.received = None
        self.attempts = 0
        self.err_handler_called = None
        self.cb_handler_called = None
        self.test_flag = False

    def error_callback(self, error):
        self.received = error
        self.err_handler_called.set()

    def callback(self, update, context):
        self.received = update.message.text
        self.cb_handler_called.set()

    async def test_slot_behaviour(self, updater, mro_slots):
        async with updater:
            for at in updater.__slots__:
                at = f"_Updater{at}" if at.startswith("__") and not at.endswith("__") else at
                assert getattr(updater, at, "err") != "err", f"got extra slot '{at}'"
            assert len(mro_slots(updater)) == len(set(mro_slots(updater))), "duplicate slot"

    def test_init(self, bot):
        queue = asyncio.Queue()
        updater = Updater(bot=bot, update_queue=queue)
        assert updater.bot is bot
        assert updater.update_queue is queue

    async def test_initialize(self, bot, monkeypatch):
        async def initialize_bot(*args, **kwargs):
            self.test_flag = True

        async with make_bot(token=bot.token) as test_bot:
            monkeypatch.setattr(test_bot, "initialize", initialize_bot)

            updater = Updater(bot=test_bot, update_queue=asyncio.Queue())
            await updater.initialize()

        assert self.test_flag

    async def test_shutdown(self, bot, monkeypatch):
        async def shutdown_bot(*args, **kwargs):
            self.test_flag = True

        async with make_bot(token=bot.token) as test_bot:
            monkeypatch.setattr(test_bot, "shutdown", shutdown_bot)

            updater = Updater(bot=test_bot, update_queue=asyncio.Queue())
            await updater.initialize()
            await updater.shutdown()

        assert self.test_flag

    async def test_multiple_inits_and_shutdowns(self, updater, monkeypatch):
        self.test_flag = defaultdict(int)

        async def initialize(*args, **kargs):
            self.test_flag["init"] += 1

        async def shutdown(*args, **kwargs):
            self.test_flag["shutdown"] += 1

        monkeypatch.setattr(updater.bot, "initialize", initialize)
        monkeypatch.setattr(updater.bot, "shutdown", shutdown)

        await updater.initialize()
        await updater.initialize()
        await updater.initialize()
        await updater.shutdown()
        await updater.shutdown()
        await updater.shutdown()

        assert self.test_flag["init"] == 1
        assert self.test_flag["shutdown"] == 1

    async def test_multiple_init_cycles(self, updater):
        # nothing really to assert - this should just not fail
        async with updater:
            await updater.bot.get_me()
        async with updater:
            await updater.bot.get_me()

    @pytest.mark.parametrize("method", ["start_polling", "start_webhook"])
    async def test_start_without_initialize(self, updater, method):
        with pytest.raises(RuntimeError, match="not initialized"):
            await getattr(updater, method)()

    @pytest.mark.parametrize("method", ["start_polling", "start_webhook"])
    async def test_shutdown_while_running(self, updater, method, monkeypatch):
        async def set_webhook(*args, **kwargs):
            return True

        monkeypatch.setattr(updater.bot, "set_webhook", set_webhook)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port

        async with updater:
            if "webhook" in method:
                await getattr(updater, method)(
                    ip_address=ip,
                    port=port,
                )
            else:
                await getattr(updater, method)()

            with pytest.raises(RuntimeError, match="still running"):
                await updater.shutdown()
            await updater.stop()

    async def test_context_manager(self, monkeypatch, updater):
        async def initialize(*args, **kwargs):
            self.test_flag = ["initialize"]

        async def shutdown(*args, **kwargs):
            self.test_flag.append("stop")

        monkeypatch.setattr(Updater, "initialize", initialize)
        monkeypatch.setattr(Updater, "shutdown", shutdown)

        async with updater:
            pass

        assert self.test_flag == ["initialize", "stop"]

    async def test_context_manager_exception_on_init(self, monkeypatch, updater):
        async def initialize(*args, **kwargs):
            raise RuntimeError("initialize")

        async def shutdown(*args):
            self.test_flag = "stop"

        monkeypatch.setattr(Updater, "initialize", initialize)
        monkeypatch.setattr(Updater, "shutdown", shutdown)

        with pytest.raises(RuntimeError, match="initialize"):
            async with updater:
                pass

        assert self.test_flag == "stop"

    @pytest.mark.parametrize("drop_pending_updates", (True, False))
    async def test_polling_basic(self, monkeypatch, updater, drop_pending_updates):
        updates = asyncio.Queue()
        await updates.put(Update(update_id=1))
        await updates.put(Update(update_id=2))

        async def get_updates(*args, **kwargs):
            next_update = await updates.get()
            updates.task_done()
            return [next_update]

        orig_del_webhook = updater.bot.delete_webhook

        async def delete_webhook(*args, **kwargs):
            # Dropping pending updates is done by passing the parameter to delete_webhook
            if kwargs.get("drop_pending_updates"):
                self.message_count += 1
            return await orig_del_webhook(*args, **kwargs)

        monkeypatch.setattr(updater.bot, "get_updates", get_updates)
        monkeypatch.setattr(updater.bot, "delete_webhook", delete_webhook)

        async with updater:
            return_value = await updater.start_polling(drop_pending_updates=drop_pending_updates)
            assert return_value is updater.update_queue
            assert updater.running
            await updates.join()
            await updater.stop()
            assert not updater.running
            assert not (await updater.bot.get_webhook_info()).url
            if drop_pending_updates:
                assert self.message_count == 1
            else:
                assert self.message_count == 0

            await updates.put(Update(update_id=3))
            await updates.put(Update(update_id=4))

            # We call the same logic twice to make sure that restarting the updater works as well
            await updater.start_polling(drop_pending_updates=drop_pending_updates)
            assert updater.running
            await updates.join()
            await updater.stop()
            assert not updater.running
            assert not (await updater.bot.get_webhook_info()).url

        self.received = []
        self.message_count = 0
        while not updater.update_queue.empty():
            update = updater.update_queue.get_nowait()
            self.message_count += 1
            self.received.append(update.update_id)

        assert self.message_count == 4
        assert self.received == [1, 2, 3, 4]

    async def test_start_polling_already_running(self, updater):
        async with updater:
            await updater.start_polling()
            task = asyncio.create_task(updater.start_polling())
            with pytest.raises(RuntimeError, match="already running"):
                await task
            await updater.stop()
            with pytest.raises(RuntimeError, match="not running"):
                await updater.stop()

    async def test_start_polling_get_updates_parameters(self, updater, monkeypatch):
        update_queue = asyncio.Queue()
        await update_queue.put(Update(update_id=1))

        expected = dict(
            timeout=10,
            read_timeout=2,
            write_timeout=DEFAULT_NONE,
            connect_timeout=DEFAULT_NONE,
            pool_timeout=DEFAULT_NONE,
            allowed_updates=None,
            api_kwargs=None,
        )

        async def get_updates(*args, **kwargs):
            for key, value in expected.items():
                assert kwargs.pop(key, None) == value

            offset = kwargs.pop("offset", None)
            # Check that we don't get any unexpected kwargs
            assert kwargs == {}

            if offset is not None and self.message_count != 0:
                assert offset == self.message_count + 1, "get_updates got wrong `offset` parameter"

            update = await update_queue.get()
            self.message_count = update.update_id
            update_queue.task_done()
            return [update]

        monkeypatch.setattr(updater.bot, "get_updates", get_updates)

        async with updater:
            await updater.start_polling()
            await update_queue.join()
            await updater.stop()

            expected = dict(
                timeout=42,
                read_timeout=43,
                write_timeout=44,
                connect_timeout=45,
                pool_timeout=46,
                allowed_updates=["message"],
                api_kwargs=None,
            )

            await update_queue.put(Update(update_id=2))
            await updater.start_polling(
                timeout=42,
                read_timeout=43,
                write_timeout=44,
                connect_timeout=45,
                pool_timeout=46,
                allowed_updates=["message"],
            )
            await update_queue.join()
            await updater.stop()

    @pytest.mark.parametrize("exception_class", (InvalidToken, TelegramError))
    @pytest.mark.parametrize("retries", (3, 0))
    async def test_start_polling_bootstrap_retries(
        self, updater, monkeypatch, exception_class, retries
    ):
        async def do_request(*args, **kwargs):
            self.message_count += 1
            raise exception_class(str(self.message_count))

        async with updater:
            # Patch within the context so that updater.bot.initialize can still be called
            # by the context manager
            monkeypatch.setattr(HTTPXRequest, "do_request", do_request)

            if exception_class == InvalidToken:
                with pytest.raises(InvalidToken, match="1"):
                    await updater.start_polling(bootstrap_retries=retries)
            else:
                with pytest.raises(TelegramError, match=str(retries + 1)):
                    await updater.start_polling(bootstrap_retries=retries)

    @pytest.mark.parametrize(
        "error,callback_should_be_called",
        argvalues=[
            (TelegramError("TestMessage"), True),
            (RetryAfter(1), False),
            (TimedOut("TestMessage"), False),
        ],
        ids=("TelegramError", "RetryAfter", "TimedOut"),
    )
    @pytest.mark.parametrize("custom_error_callback", [True, False])
    async def test_start_polling_exceptions_and_error_callback(
        self, monkeypatch, updater, error, callback_should_be_called, custom_error_callback, caplog
    ):
        get_updates_event = asyncio.Event()

        async def get_updates(*args, **kwargs):
            # So that the main task has a chance to be called
            await asyncio.sleep(0)

            get_updates_event.set()
            raise error

        monkeypatch.setattr(updater.bot, "get_updates", get_updates)
        monkeypatch.setattr(updater.bot, "set_webhook", lambda *args, **kwargs: True)

        with pytest.raises(TypeError, match="`error_callback` must not be a coroutine function"):
            await updater.start_polling(error_callback=get_updates)

        async with updater:
            self.err_handler_called = asyncio.Event()

            with caplog.at_level(logging.ERROR):
                if custom_error_callback:
                    await updater.start_polling(error_callback=self.error_callback)
                else:
                    await updater.start_polling()

                # Also makes sure that the error handler was called
                await get_updates_event.wait()

                if callback_should_be_called:
                    # Make sure that the error handler was called
                    if custom_error_callback:
                        assert self.received == error
                    else:
                        assert len(caplog.records) > 0
                        records = (record.getMessage() for record in caplog.records)
                        assert "Error while getting Updates: TestMessage" in records

                # Make sure that get_updates was called
                assert get_updates_event.is_set()

            # Make sure that Updater polling keeps running
            self.err_handler_called.clear()
            get_updates_event.clear()
            caplog.clear()

            # Also makes sure that the error handler was called
            await get_updates_event.wait()

            if callback_should_be_called:
                if callback_should_be_called:
                    if custom_error_callback:
                        assert self.received == error
                    else:
                        assert len(caplog.records) > 0
                        records = (record.getMessage() for record in caplog.records)
                        assert "Error while getting Updates: TestMessage" in records
            await updater.stop()

    async def test_start_polling_unexpected_shutdown(self, updater, monkeypatch, caplog):
        update_queue = asyncio.Queue()
        await update_queue.put(Update(update_id=1))
        await update_queue.put(Update(update_id=2))
        first_update_event = asyncio.Event()
        second_update_event = asyncio.Event()

        async def get_updates(*args, **kwargs):
            self.message_count = kwargs.get("offset")
            update = await update_queue.get()
            if update.update_id == 1:
                first_update_event.set()
            else:
                await second_update_event.wait()
            return [update]

        monkeypatch.setattr(updater.bot, "get_updates", get_updates)

        async with updater:
            with caplog.at_level(logging.ERROR):
                await updater.start_polling()

                await first_update_event.wait()
                # Unfortunately we need to use the private attribute here to produce the problem
                updater._running = False
                second_update_event.set()

                await asyncio.sleep(0.1)
                assert caplog.records
                records = (record.getMessage() for record in caplog.records)
                assert any("Updater stopped unexpectedly." in record for record in records)

        # Make sure that the update_id offset wasn't increased
        assert self.message_count == 2

    async def test_start_polling_not_running_after_failure(self, updater, monkeypatch):
        # Unfortunately we have to use some internal logic to trigger an exception
        async def _start_polling(*args, **kwargs):
            raise Exception("Test Exception")

        monkeypatch.setattr(Updater, "_start_polling", _start_polling)

        async with updater:
            with pytest.raises(Exception, match="Test Exception"):
                await updater.start_polling()
            assert updater.running is False

    async def test_polling_update_de_json_fails(self, monkeypatch, updater, caplog):
        updates = asyncio.Queue()
        raise_exception = True
        await updates.put(Update(update_id=1))

        async def get_updates(*args, **kwargs):
            if raise_exception:
                await asyncio.sleep(0.01)
                raise TypeError("Invalid Data")

            next_update = await updates.get()
            updates.task_done()
            return [next_update]

        orig_del_webhook = updater.bot.delete_webhook

        async def delete_webhook(*args, **kwargs):
            # Dropping pending updates is done by passing the parameter to delete_webhook
            if kwargs.get("drop_pending_updates"):
                self.message_count += 1
            return await orig_del_webhook(*args, **kwargs)

        monkeypatch.setattr(updater.bot, "get_updates", get_updates)
        monkeypatch.setattr(updater.bot, "delete_webhook", delete_webhook)

        async with updater:
            with caplog.at_level(logging.CRITICAL):
                await updater.start_polling()
                assert updater.running
                await asyncio.sleep(1)

            assert len(caplog.records) > 0
            for record in caplog.records:
                assert record.getMessage().startswith("Something went wrong processing")

            # Make sure that everything works fine again when receiving proper updates
            raise_exception = False
            await asyncio.sleep(0.5)
            caplog.clear()
            with caplog.at_level(logging.CRITICAL):
                await updates.join()
            assert len(caplog.records) == 0

            await updater.stop()
            assert not updater.running

    @pytest.mark.parametrize("ext_bot", [True, False])
    @pytest.mark.parametrize("drop_pending_updates", (True, False))
    @pytest.mark.parametrize("secret_token", ["SecretToken", None])
    async def test_webhook_basic(
        self, monkeypatch, updater, drop_pending_updates, ext_bot, secret_token
    ):
        # Testing with both ExtBot and Bot to make sure any logic in WebhookHandler
        # that depends on this distinction works
        if ext_bot and not isinstance(updater.bot, ExtBot):
            updater.bot = ExtBot(updater.bot.token)
        if not ext_bot and not type(updater.bot) is Bot:
            updater.bot = DictBot(updater.bot.token)

        async def delete_webhook(*args, **kwargs):
            # Dropping pending updates is done by passing the parameter to delete_webhook
            if kwargs.get("drop_pending_updates"):
                self.message_count += 1
            return True

        async def set_webhook(*args, **kwargs):
            return True

        monkeypatch.setattr(updater.bot, "set_webhook", set_webhook)
        monkeypatch.setattr(updater.bot, "delete_webhook", delete_webhook)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port

        async with updater:
            return_value = await updater.start_webhook(
                drop_pending_updates=drop_pending_updates,
                ip_address=ip,
                port=port,
                url_path="TOKEN",
                secret_token=secret_token,
            )
            assert return_value is updater.update_queue
            assert updater.running

            # Now, we send an update to the server
            update = make_message_update("Webhook")
            await send_webhook_message(
                ip, port, update.to_json(), "TOKEN", secret_token=secret_token
            )
            assert (await updater.update_queue.get()).to_dict() == update.to_dict()

            # Returns Not Found if path is incorrect
            response = await send_webhook_message(ip, port, "123456", "webhook_handler.py")
            assert response.status_code == HTTPStatus.NOT_FOUND

            # Returns METHOD_NOT_ALLOWED if method is not allowed
            response = await send_webhook_message(ip, port, None, "TOKEN", get_method="HEAD")
            assert response.status_code == HTTPStatus.METHOD_NOT_ALLOWED

            if secret_token:
                # Returns Forbidden if no secret token is set
                response_text = "<html><title>403: {0}</title><body>403: {0}</body></html>"
                response = await send_webhook_message(ip, port, update.to_json(), "TOKEN")
                assert response.status_code == HTTPStatus.FORBIDDEN
                assert response.text == response_text.format(
                    "Request did not include the secret token"
                )

                # Returns Forbidden if the secret token is wrong
                response = await send_webhook_message(
                    ip, port, update.to_json(), "TOKEN", secret_token="NotTheSecretToken"
                )
                assert response.status_code == HTTPStatus.FORBIDDEN
                assert response.text == response_text.format("Request had the wrong secret token")

            await updater.stop()
            assert not updater.running

            if drop_pending_updates:
                assert self.message_count == 1
            else:
                assert self.message_count == 0

            # We call the same logic twice to make sure that restarting the updater works as well
            await updater.start_webhook(
                drop_pending_updates=drop_pending_updates,
                ip_address=ip,
                port=port,
                url_path="TOKEN",
            )
            assert updater.running
            update = make_message_update("Webhook")
            await send_webhook_message(ip, port, update.to_json(), "TOKEN")
            assert (await updater.update_queue.get()).to_dict() == update.to_dict()
            await updater.stop()
            assert not updater.running

    async def test_start_webhook_already_running(self, updater, monkeypatch):
        async def return_true(*args, **kwargs):
            return True

        monkeypatch.setattr(updater.bot, "set_webhook", return_true)
        monkeypatch.setattr(updater.bot, "delete_webhook", return_true)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port
        async with updater:
            await updater.start_webhook(ip, port, url_path="TOKEN")
            task = asyncio.create_task(updater.start_webhook(ip, port, url_path="TOKEN"))
            with pytest.raises(RuntimeError, match="already running"):
                await task
            await updater.stop()
            with pytest.raises(RuntimeError, match="not running"):
                await updater.stop()

    async def test_start_webhook_parameters_passing(self, updater, monkeypatch):
        expected_delete_webhook = dict(
            drop_pending_updates=None,
        )

        expected_set_webhook = dict(
            certificate=None,
            max_connections=40,
            allowed_updates=None,
            ip_address=None,
            secret_token=None,
            **expected_delete_webhook,
        )

        async def set_webhook(*args, **kwargs):
            for key, value in expected_set_webhook.items():
                assert kwargs.pop(key, None) == value, f"set, {key}, {value}"

            assert kwargs in (
                {"url": "http://127.0.0.1:80/"},
                {"url": "http://listen:80/"},
                {"url": "https://listen-ssl:42/ssl-path"},
            )
            return True

        async def delete_webhook(*args, **kwargs):
            for key, value in expected_delete_webhook.items():
                assert kwargs.pop(key, None) == value, f"delete, {key}, {value}"

            assert kwargs == {}
            return True

        async def serve_forever(*args, **kwargs):
            kwargs.get("ready").set()

        monkeypatch.setattr(updater.bot, "set_webhook", set_webhook)
        monkeypatch.setattr(updater.bot, "delete_webhook", delete_webhook)
        monkeypatch.setattr(WebhookServer, "serve_forever", serve_forever)

        async with updater:
            await updater.start_webhook()
            await updater.stop()
            expected_delete_webhook = dict(
                drop_pending_updates=True,
                api_kwargs=None,
            )

            expected_set_webhook = dict(
                certificate=data_file("sslcert.pem").read_bytes(),
                max_connections=47,
                allowed_updates=["message"],
                ip_address="123.456.789",
                secret_token=None,
                **expected_delete_webhook,
            )

            await updater.start_webhook(
                listen="listen",
                allowed_updates=["message"],
                drop_pending_updates=True,
                ip_address="123.456.789",
                max_connections=47,
                cert=str(data_file("sslcert.pem").resolve()),
            )
            await updater.stop()

            await updater.start_webhook(
                listen="listen-ssl",
                port=42,
                url_path="ssl-path",
                allowed_updates=["message"],
                drop_pending_updates=True,
                ip_address="123.456.789",
                max_connections=47,
                cert=data_file("sslcert.pem"),
                key=data_file("sslcert.key"),
            )
            await updater.stop()

    @pytest.mark.parametrize("invalid_data", [True, False], ids=("invalid data", "valid data"))
    async def test_webhook_arbitrary_callback_data(
        self, monkeypatch, cdc_bot, invalid_data, chat_id
    ):
        """Here we only test one simple setup. telegram.ext.ExtBot.insert_callback_data is tested
        extensively in test_bot.py in conjunction with get_updates."""
        updater = Updater(bot=cdc_bot, update_queue=asyncio.Queue())

        async def return_true(*args, **kwargs):
            return True

        try:
            monkeypatch.setattr(updater.bot, "set_webhook", return_true)
            monkeypatch.setattr(updater.bot, "delete_webhook", return_true)

            ip = "127.0.0.1"
            port = randrange(1024, 49152)  # Select random port

            async with updater:
                await updater.start_webhook(ip, port, url_path="TOKEN")
                # Now, we send an update to the server
                reply_markup = InlineKeyboardMarkup.from_button(
                    InlineKeyboardButton(text="text", callback_data="callback_data")
                )
                if not invalid_data:
                    reply_markup = updater.bot.callback_data_cache.process_keyboard(reply_markup)

                update = make_message_update(
                    message="test_webhook_arbitrary_callback_data",
                    message_factory=make_message,
                    reply_markup=reply_markup,
                    user=updater.bot.bot,
                )

                await send_webhook_message(ip, port, update.to_json(), "TOKEN")
                received_update = await updater.update_queue.get()

                assert received_update.update_id == update.update_id
                message_dict = update.message.to_dict()
                received_dict = received_update.message.to_dict()
                message_dict.pop("reply_markup")
                received_dict.pop("reply_markup")
                assert message_dict == received_dict

                button = received_update.message.reply_markup.inline_keyboard[0][0]
                if invalid_data:
                    assert isinstance(button.callback_data, InvalidCallbackData)
                else:
                    assert button.callback_data == "callback_data"

                await updater.stop()
        finally:
            updater.bot.callback_data_cache.clear_callback_data()
            updater.bot.callback_data_cache.clear_callback_queries()

    async def test_webhook_invalid_ssl(self, monkeypatch, updater):
        async def return_true(*args, **kwargs):
            return True

        monkeypatch.setattr(updater.bot, "set_webhook", return_true)
        monkeypatch.setattr(updater.bot, "delete_webhook", return_true)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port
        async with updater:
            with pytest.raises(TelegramError, match="Invalid SSL"):
                await updater.start_webhook(
                    ip,
                    port,
                    url_path="TOKEN",
                    cert=Path(__file__).as_posix(),
                    key=Path(__file__).as_posix(),
                    bootstrap_retries=0,
                    drop_pending_updates=False,
                    webhook_url=None,
                    allowed_updates=None,
                )
            assert updater.running is False

    async def test_webhook_ssl_just_for_telegram(self, monkeypatch, updater):
        """Here we just test that the SSL info is pased to Telegram, but __not__ to the the
        webhook server"""

        async def set_webhook(**kwargs):
            self.test_flag.append(bool(kwargs.get("certificate")))
            return True

        async def return_true(*args, **kwargs):
            return True

        orig_wh_server_init = WebhookServer.__init__

        def webhook_server_init(*args, **kwargs):
            self.test_flag = [kwargs.get("ssl_ctx") is None]
            orig_wh_server_init(*args, **kwargs)

        monkeypatch.setattr(updater.bot, "set_webhook", set_webhook)
        monkeypatch.setattr(updater.bot, "delete_webhook", return_true)
        monkeypatch.setattr(
            "telegram.ext._utils.webhookhandler.WebhookServer.__init__", webhook_server_init
        )

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port
        async with updater:
            await updater.start_webhook(ip, port, webhook_url=None, cert=Path(__file__).as_posix())

            # Now, we send an update to the server
            update = make_message_update(message="test_message")
            await send_webhook_message(ip, port, update.to_json())
            assert (await updater.update_queue.get()).to_dict() == update.to_dict()
            assert self.test_flag == [True, True]
            await updater.stop()

    @pytest.mark.parametrize("exception_class", (InvalidToken, TelegramError))
    @pytest.mark.parametrize("retries", (3, 0))
    async def test_start_webhook_bootstrap_retries(
        self, updater, monkeypatch, exception_class, retries
    ):
        async def do_request(*args, **kwargs):
            self.message_count += 1
            raise exception_class(str(self.message_count))

        async with updater:
            # Patch within the context so that updater.bot.initialize can still be called
            # by the context manager
            monkeypatch.setattr(HTTPXRequest, "do_request", do_request)

            if exception_class == InvalidToken:
                with pytest.raises(InvalidToken, match="1"):
                    await updater.start_webhook(bootstrap_retries=retries)
            else:
                with pytest.raises(TelegramError, match=str(retries + 1)):
                    await updater.start_webhook(
                        bootstrap_retries=retries,
                    )

    async def test_webhook_invalid_posts(self, updater, monkeypatch):
        async def return_true(*args, **kwargs):
            return True

        monkeypatch.setattr(updater.bot, "set_webhook", return_true)
        monkeypatch.setattr(updater.bot, "delete_webhook", return_true)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)

        async with updater:
            await updater.start_webhook(listen=ip, port=port)

            response = await send_webhook_message(ip, port, None, content_type="invalid")
            assert response.status_code == HTTPStatus.FORBIDDEN

            response = await send_webhook_message(
                ip,
                port,
                payload_str="<root><bla>data</bla></root>",
                content_type="application/xml",
            )
            assert response.status_code == HTTPStatus.FORBIDDEN

            response = await send_webhook_message(ip, port, "dummy-payload", content_len=None)
            assert response.status_code == HTTPStatus.INTERNAL_SERVER_ERROR

            # httpx already complains about bad content length in _send_webhook_message
            # before the requests below reach the webhook, but not testing this is probably
            # okay
            # response = await send_webhook_message(
            #   ip, port, 'dummy-payload', content_len=-2)
            # assert response.status_code == HTTPStatus.FORBIDDEN
            # response = await send_webhook_message(
            #   ip, port, 'dummy-payload', content_len='not-a-number')
            # assert response.status_code == HTTPStatus.INTERNAL_SERVER_ERROR

            await updater.stop()

    async def test_webhook_update_de_json_fails(self, monkeypatch, updater, caplog):
        async def delete_webhook(*args, **kwargs):
            return True

        async def set_webhook(*args, **kwargs):
            return True

        def de_json_fails(*args, **kwargs):
            raise TypeError("Invalid input")

        monkeypatch.setattr(updater.bot, "set_webhook", set_webhook)
        monkeypatch.setattr(updater.bot, "delete_webhook", delete_webhook)
        orig_de_json = Update.de_json
        monkeypatch.setattr(Update, "de_json", de_json_fails)

        ip = "127.0.0.1"
        port = randrange(1024, 49152)  # Select random port

        async with updater:
            return_value = await updater.start_webhook(
                ip_address=ip,
                port=port,
                url_path="TOKEN",
            )
            assert return_value is updater.update_queue
            assert updater.running

            # Now, we send an update to the server
            update = make_message_update("Webhook")
            with caplog.at_level(logging.CRITICAL):
                await send_webhook_message(ip, port, update.to_json(), "TOKEN")

            assert len(caplog.records) == 1
            assert caplog.records[-1].getMessage().startswith("Something went wrong processing")

            # Make sure that everything works fine again when receiving proper updates
            caplog.clear()
            with caplog.at_level(logging.CRITICAL):
                monkeypatch.setattr(Update, "de_json", orig_de_json)
                await send_webhook_message(ip, port, update.to_json(), "TOKEN")
                assert (await updater.update_queue.get()).to_dict() == update.to_dict()
            assert len(caplog.records) == 0

            await updater.stop()
            assert not updater.running