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diff --git a/synapse/rest/media/thumbnail_resource.py b/synapse/rest/media/thumbnail_resource.py
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+# Copyright 2014-2016 OpenMarket Ltd
+# Copyright 2020-2021 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+
+import logging
+from typing import TYPE_CHECKING, Any, Dict, List, Optional, Tuple
+
+from synapse.api.errors import Codes, SynapseError, cs_error
+from synapse.config.repository import THUMBNAIL_SUPPORTED_MEDIA_FORMAT_MAP
+from synapse.http.server import (
+    DirectServeJsonResource,
+    respond_with_json,
+    set_corp_headers,
+    set_cors_headers,
+)
+from synapse.http.servlet import parse_integer, parse_string
+from synapse.http.site import SynapseRequest
+from synapse.media._base import (
+    FileInfo,
+    ThumbnailInfo,
+    parse_media_id,
+    respond_404,
+    respond_with_file,
+    respond_with_responder,
+)
+from synapse.media.media_storage import MediaStorage
+
+if TYPE_CHECKING:
+    from synapse.media.media_repository import MediaRepository
+    from synapse.server import HomeServer
+
+logger = logging.getLogger(__name__)
+
+
+class ThumbnailResource(DirectServeJsonResource):
+    isLeaf = True
+
+    def __init__(
+        self,
+        hs: "HomeServer",
+        media_repo: "MediaRepository",
+        media_storage: MediaStorage,
+    ):
+        super().__init__()
+
+        self.store = hs.get_datastores().main
+        self.media_repo = media_repo
+        self.media_storage = media_storage
+        self.dynamic_thumbnails = hs.config.media.dynamic_thumbnails
+        self.server_name = hs.hostname
+
+    async def _async_render_GET(self, request: SynapseRequest) -> None:
+        set_cors_headers(request)
+        set_corp_headers(request)
+        server_name, media_id, _ = parse_media_id(request)
+        width = parse_integer(request, "width", required=True)
+        height = parse_integer(request, "height", required=True)
+        method = parse_string(request, "method", "scale")
+        # TODO Parse the Accept header to get an prioritised list of thumbnail types.
+        m_type = "image/png"
+
+        if server_name == self.server_name:
+            if self.dynamic_thumbnails:
+                await self._select_or_generate_local_thumbnail(
+                    request, media_id, width, height, method, m_type
+                )
+            else:
+                await self._respond_local_thumbnail(
+                    request, media_id, width, height, method, m_type
+                )
+            self.media_repo.mark_recently_accessed(None, media_id)
+        else:
+            if self.dynamic_thumbnails:
+                await self._select_or_generate_remote_thumbnail(
+                    request, server_name, media_id, width, height, method, m_type
+                )
+            else:
+                await self._respond_remote_thumbnail(
+                    request, server_name, media_id, width, height, method, m_type
+                )
+            self.media_repo.mark_recently_accessed(server_name, media_id)
+
+    async def _respond_local_thumbnail(
+        self,
+        request: SynapseRequest,
+        media_id: str,
+        width: int,
+        height: int,
+        method: str,
+        m_type: str,
+    ) -> None:
+        media_info = await self.store.get_local_media(media_id)
+
+        if not media_info:
+            respond_404(request)
+            return
+        if media_info["quarantined_by"]:
+            logger.info("Media is quarantined")
+            respond_404(request)
+            return
+
+        thumbnail_infos = await self.store.get_local_media_thumbnails(media_id)
+        await self._select_and_respond_with_thumbnail(
+            request,
+            width,
+            height,
+            method,
+            m_type,
+            thumbnail_infos,
+            media_id,
+            media_id,
+            url_cache=bool(media_info["url_cache"]),
+            server_name=None,
+        )
+
+    async def _select_or_generate_local_thumbnail(
+        self,
+        request: SynapseRequest,
+        media_id: str,
+        desired_width: int,
+        desired_height: int,
+        desired_method: str,
+        desired_type: str,
+    ) -> None:
+        media_info = await self.store.get_local_media(media_id)
+
+        if not media_info:
+            respond_404(request)
+            return
+        if media_info["quarantined_by"]:
+            logger.info("Media is quarantined")
+            respond_404(request)
+            return
+
+        thumbnail_infos = await self.store.get_local_media_thumbnails(media_id)
+        for info in thumbnail_infos:
+            t_w = info["thumbnail_width"] == desired_width
+            t_h = info["thumbnail_height"] == desired_height
+            t_method = info["thumbnail_method"] == desired_method
+            t_type = info["thumbnail_type"] == desired_type
+
+            if t_w and t_h and t_method and t_type:
+                file_info = FileInfo(
+                    server_name=None,
+                    file_id=media_id,
+                    url_cache=media_info["url_cache"],
+                    thumbnail=ThumbnailInfo(
+                        width=info["thumbnail_width"],
+                        height=info["thumbnail_height"],
+                        type=info["thumbnail_type"],
+                        method=info["thumbnail_method"],
+                    ),
+                )
+
+                t_type = file_info.thumbnail_type
+                t_length = info["thumbnail_length"]
+
+                responder = await self.media_storage.fetch_media(file_info)
+                if responder:
+                    await respond_with_responder(request, responder, t_type, t_length)
+                    return
+
+        logger.debug("We don't have a thumbnail of that size. Generating")
+
+        # Okay, so we generate one.
+        file_path = await self.media_repo.generate_local_exact_thumbnail(
+            media_id,
+            desired_width,
+            desired_height,
+            desired_method,
+            desired_type,
+            url_cache=bool(media_info["url_cache"]),
+        )
+
+        if file_path:
+            await respond_with_file(request, desired_type, file_path)
+        else:
+            logger.warning("Failed to generate thumbnail")
+            raise SynapseError(400, "Failed to generate thumbnail.")
+
+    async def _select_or_generate_remote_thumbnail(
+        self,
+        request: SynapseRequest,
+        server_name: str,
+        media_id: str,
+        desired_width: int,
+        desired_height: int,
+        desired_method: str,
+        desired_type: str,
+    ) -> None:
+        media_info = await self.media_repo.get_remote_media_info(server_name, media_id)
+
+        thumbnail_infos = await self.store.get_remote_media_thumbnails(
+            server_name, media_id
+        )
+
+        file_id = media_info["filesystem_id"]
+
+        for info in thumbnail_infos:
+            t_w = info["thumbnail_width"] == desired_width
+            t_h = info["thumbnail_height"] == desired_height
+            t_method = info["thumbnail_method"] == desired_method
+            t_type = info["thumbnail_type"] == desired_type
+
+            if t_w and t_h and t_method and t_type:
+                file_info = FileInfo(
+                    server_name=server_name,
+                    file_id=media_info["filesystem_id"],
+                    thumbnail=ThumbnailInfo(
+                        width=info["thumbnail_width"],
+                        height=info["thumbnail_height"],
+                        type=info["thumbnail_type"],
+                        method=info["thumbnail_method"],
+                    ),
+                )
+
+                t_type = file_info.thumbnail_type
+                t_length = info["thumbnail_length"]
+
+                responder = await self.media_storage.fetch_media(file_info)
+                if responder:
+                    await respond_with_responder(request, responder, t_type, t_length)
+                    return
+
+        logger.debug("We don't have a thumbnail of that size. Generating")
+
+        # Okay, so we generate one.
+        file_path = await self.media_repo.generate_remote_exact_thumbnail(
+            server_name,
+            file_id,
+            media_id,
+            desired_width,
+            desired_height,
+            desired_method,
+            desired_type,
+        )
+
+        if file_path:
+            await respond_with_file(request, desired_type, file_path)
+        else:
+            logger.warning("Failed to generate thumbnail")
+            raise SynapseError(400, "Failed to generate thumbnail.")
+
+    async def _respond_remote_thumbnail(
+        self,
+        request: SynapseRequest,
+        server_name: str,
+        media_id: str,
+        width: int,
+        height: int,
+        method: str,
+        m_type: str,
+    ) -> None:
+        # TODO: Don't download the whole remote file
+        # We should proxy the thumbnail from the remote server instead of
+        # downloading the remote file and generating our own thumbnails.
+        media_info = await self.media_repo.get_remote_media_info(server_name, media_id)
+
+        thumbnail_infos = await self.store.get_remote_media_thumbnails(
+            server_name, media_id
+        )
+        await self._select_and_respond_with_thumbnail(
+            request,
+            width,
+            height,
+            method,
+            m_type,
+            thumbnail_infos,
+            media_id,
+            media_info["filesystem_id"],
+            url_cache=False,
+            server_name=server_name,
+        )
+
+    async def _select_and_respond_with_thumbnail(
+        self,
+        request: SynapseRequest,
+        desired_width: int,
+        desired_height: int,
+        desired_method: str,
+        desired_type: str,
+        thumbnail_infos: List[Dict[str, Any]],
+        media_id: str,
+        file_id: str,
+        url_cache: bool,
+        server_name: Optional[str] = None,
+    ) -> None:
+        """
+        Respond to a request with an appropriate thumbnail from the previously generated thumbnails.
+
+        Args:
+            request: The incoming request.
+            desired_width: The desired width, the returned thumbnail may be larger than this.
+            desired_height: The desired height, the returned thumbnail may be larger than this.
+            desired_method: The desired method used to generate the thumbnail.
+            desired_type: The desired content-type of the thumbnail.
+            thumbnail_infos: A list of dictionaries of candidate thumbnails.
+            file_id: The ID of the media that a thumbnail is being requested for.
+            url_cache: True if this is from a URL cache.
+            server_name: The server name, if this is a remote thumbnail.
+        """
+        logger.debug(
+            "_select_and_respond_with_thumbnail: media_id=%s desired=%sx%s (%s) thumbnail_infos=%s",
+            media_id,
+            desired_width,
+            desired_height,
+            desired_method,
+            thumbnail_infos,
+        )
+
+        # If `dynamic_thumbnails` is enabled, we expect Synapse to go down a
+        # different code path to handle it.
+        assert not self.dynamic_thumbnails
+
+        if thumbnail_infos:
+            file_info = self._select_thumbnail(
+                desired_width,
+                desired_height,
+                desired_method,
+                desired_type,
+                thumbnail_infos,
+                file_id,
+                url_cache,
+                server_name,
+            )
+            if not file_info:
+                logger.info("Couldn't find a thumbnail matching the desired inputs")
+                respond_404(request)
+                return
+
+            # The thumbnail property must exist.
+            assert file_info.thumbnail is not None
+
+            responder = await self.media_storage.fetch_media(file_info)
+            if responder:
+                await respond_with_responder(
+                    request,
+                    responder,
+                    file_info.thumbnail.type,
+                    file_info.thumbnail.length,
+                )
+                return
+
+            # If we can't find the thumbnail we regenerate it. This can happen
+            # if e.g. we've deleted the thumbnails but still have the original
+            # image somewhere.
+            #
+            # Since we have an entry for the thumbnail in the DB we a) know we
+            # have have successfully generated the thumbnail in the past (so we
+            # don't need to worry about repeatedly failing to generate
+            # thumbnails), and b) have already calculated that appropriate
+            # width/height/method so we can just call the "generate exact"
+            # methods.
+
+            # First let's check that we do actually have the original image
+            # still. This will throw a 404 if we don't.
+            # TODO: We should refetch the thumbnails for remote media.
+            await self.media_storage.ensure_media_is_in_local_cache(
+                FileInfo(server_name, file_id, url_cache=url_cache)
+            )
+
+            if server_name:
+                await self.media_repo.generate_remote_exact_thumbnail(
+                    server_name,
+                    file_id=file_id,
+                    media_id=media_id,
+                    t_width=file_info.thumbnail.width,
+                    t_height=file_info.thumbnail.height,
+                    t_method=file_info.thumbnail.method,
+                    t_type=file_info.thumbnail.type,
+                )
+            else:
+                await self.media_repo.generate_local_exact_thumbnail(
+                    media_id=media_id,
+                    t_width=file_info.thumbnail.width,
+                    t_height=file_info.thumbnail.height,
+                    t_method=file_info.thumbnail.method,
+                    t_type=file_info.thumbnail.type,
+                    url_cache=url_cache,
+                )
+
+            responder = await self.media_storage.fetch_media(file_info)
+            await respond_with_responder(
+                request,
+                responder,
+                file_info.thumbnail.type,
+                file_info.thumbnail.length,
+            )
+        else:
+            # This might be because:
+            # 1. We can't create thumbnails for the given media (corrupted or
+            #    unsupported file type), or
+            # 2. The thumbnailing process never ran or errored out initially
+            #    when the media was first uploaded (these bugs should be
+            #    reported and fixed).
+            # Note that we don't attempt to generate a thumbnail now because
+            # `dynamic_thumbnails` is disabled.
+            logger.info("Failed to find any generated thumbnails")
+
+            respond_with_json(
+                request,
+                400,
+                cs_error(
+                    "Cannot find any thumbnails for the requested media (%r). This might mean the media is not a supported_media_format=(%s) or that thumbnailing failed for some other reason. (Dynamic thumbnails are disabled on this server.)"
+                    % (
+                        request.postpath,
+                        ", ".join(THUMBNAIL_SUPPORTED_MEDIA_FORMAT_MAP.keys()),
+                    ),
+                    code=Codes.UNKNOWN,
+                ),
+                send_cors=True,
+            )
+
+    def _select_thumbnail(
+        self,
+        desired_width: int,
+        desired_height: int,
+        desired_method: str,
+        desired_type: str,
+        thumbnail_infos: List[Dict[str, Any]],
+        file_id: str,
+        url_cache: bool,
+        server_name: Optional[str],
+    ) -> Optional[FileInfo]:
+        """
+        Choose an appropriate thumbnail from the previously generated thumbnails.
+
+        Args:
+            desired_width: The desired width, the returned thumbnail may be larger than this.
+            desired_height: The desired height, the returned thumbnail may be larger than this.
+            desired_method: The desired method used to generate the thumbnail.
+            desired_type: The desired content-type of the thumbnail.
+            thumbnail_infos: A list of dictionaries of candidate thumbnails.
+            file_id: The ID of the media that a thumbnail is being requested for.
+            url_cache: True if this is from a URL cache.
+            server_name: The server name, if this is a remote thumbnail.
+
+        Returns:
+             The thumbnail which best matches the desired parameters.
+        """
+        desired_method = desired_method.lower()
+
+        # The chosen thumbnail.
+        thumbnail_info = None
+
+        d_w = desired_width
+        d_h = desired_height
+
+        if desired_method == "crop":
+            # Thumbnails that match equal or larger sizes of desired width/height.
+            crop_info_list: List[Tuple[int, int, int, bool, int, Dict[str, Any]]] = []
+            # Other thumbnails.
+            crop_info_list2: List[Tuple[int, int, int, bool, int, Dict[str, Any]]] = []
+            for info in thumbnail_infos:
+                # Skip thumbnails generated with different methods.
+                if info["thumbnail_method"] != "crop":
+                    continue
+
+                t_w = info["thumbnail_width"]
+                t_h = info["thumbnail_height"]
+                aspect_quality = abs(d_w * t_h - d_h * t_w)
+                min_quality = 0 if d_w <= t_w and d_h <= t_h else 1
+                size_quality = abs((d_w - t_w) * (d_h - t_h))
+                type_quality = desired_type != info["thumbnail_type"]
+                length_quality = info["thumbnail_length"]
+                if t_w >= d_w or t_h >= d_h:
+                    crop_info_list.append(
+                        (
+                            aspect_quality,
+                            min_quality,
+                            size_quality,
+                            type_quality,
+                            length_quality,
+                            info,
+                        )
+                    )
+                else:
+                    crop_info_list2.append(
+                        (
+                            aspect_quality,
+                            min_quality,
+                            size_quality,
+                            type_quality,
+                            length_quality,
+                            info,
+                        )
+                    )
+            # Pick the most appropriate thumbnail. Some values of `desired_width` and
+            # `desired_height` may result in a tie, in which case we avoid comparing on
+            # the thumbnail info dictionary and pick the thumbnail that appears earlier
+            # in the list of candidates.
+            if crop_info_list:
+                thumbnail_info = min(crop_info_list, key=lambda t: t[:-1])[-1]
+            elif crop_info_list2:
+                thumbnail_info = min(crop_info_list2, key=lambda t: t[:-1])[-1]
+        elif desired_method == "scale":
+            # Thumbnails that match equal or larger sizes of desired width/height.
+            info_list: List[Tuple[int, bool, int, Dict[str, Any]]] = []
+            # Other thumbnails.
+            info_list2: List[Tuple[int, bool, int, Dict[str, Any]]] = []
+
+            for info in thumbnail_infos:
+                # Skip thumbnails generated with different methods.
+                if info["thumbnail_method"] != "scale":
+                    continue
+
+                t_w = info["thumbnail_width"]
+                t_h = info["thumbnail_height"]
+                size_quality = abs((d_w - t_w) * (d_h - t_h))
+                type_quality = desired_type != info["thumbnail_type"]
+                length_quality = info["thumbnail_length"]
+                if t_w >= d_w or t_h >= d_h:
+                    info_list.append((size_quality, type_quality, length_quality, info))
+                else:
+                    info_list2.append(
+                        (size_quality, type_quality, length_quality, info)
+                    )
+            # Pick the most appropriate thumbnail. Some values of `desired_width` and
+            # `desired_height` may result in a tie, in which case we avoid comparing on
+            # the thumbnail info dictionary and pick the thumbnail that appears earlier
+            # in the list of candidates.
+            if info_list:
+                thumbnail_info = min(info_list, key=lambda t: t[:-1])[-1]
+            elif info_list2:
+                thumbnail_info = min(info_list2, key=lambda t: t[:-1])[-1]
+
+        if thumbnail_info:
+            return FileInfo(
+                file_id=file_id,
+                url_cache=url_cache,
+                server_name=server_name,
+                thumbnail=ThumbnailInfo(
+                    width=thumbnail_info["thumbnail_width"],
+                    height=thumbnail_info["thumbnail_height"],
+                    type=thumbnail_info["thumbnail_type"],
+                    method=thumbnail_info["thumbnail_method"],
+                    length=thumbnail_info["thumbnail_length"],
+                ),
+            )
+
+        # No matching thumbnail was found.
+        return None