diff --git a/changelog.d/9093.misc b/changelog.d/9093.misc
new file mode 100644
index 0000000000..53eb8f72a8
--- /dev/null
+++ b/changelog.d/9093.misc
@@ -0,0 +1 @@
+Add type hints to media repository.
diff --git a/synapse/rest/media/v1/_base.py b/synapse/rest/media/v1/_base.py
index 47c2b44bff..31a41e4a27 100644
--- a/synapse/rest/media/v1/_base.py
+++ b/synapse/rest/media/v1/_base.py
@@ -1,6 +1,6 @@
 # -*- coding: utf-8 -*-
 # Copyright 2014-2016 OpenMarket Ltd
-# Copyright 2019 New Vector Ltd
+# Copyright 2019-2021 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.
@@ -17,10 +17,11 @@
 import logging
 import os
 import urllib
-from typing import Awaitable
+from typing import Awaitable, Dict, Generator, List, Optional, Tuple
 
 from twisted.internet.interfaces import IConsumer
 from twisted.protocols.basic import FileSender
+from twisted.web.http import Request
 
 from synapse.api.errors import Codes, SynapseError, cs_error
 from synapse.http.server import finish_request, respond_with_json
@@ -46,7 +47,7 @@ TEXT_CONTENT_TYPES = [
 ]
 
 
-def parse_media_id(request):
+def parse_media_id(request: Request) -> Tuple[str, str, Optional[str]]:
     try:
         # This allows users to append e.g. /test.png to the URL. Useful for
         # clients that parse the URL to see content type.
@@ -69,7 +70,7 @@ def parse_media_id(request):
         )
 
 
-def respond_404(request):
+def respond_404(request: Request) -> None:
     respond_with_json(
         request,
         404,
@@ -79,8 +80,12 @@ def respond_404(request):
 
 
 async def respond_with_file(
-    request, media_type, file_path, file_size=None, upload_name=None
-):
+    request: Request,
+    media_type: str,
+    file_path: str,
+    file_size: Optional[int] = None,
+    upload_name: Optional[str] = None,
+) -> None:
     logger.debug("Responding with %r", file_path)
 
     if os.path.isfile(file_path):
@@ -98,15 +103,20 @@ async def respond_with_file(
         respond_404(request)
 
 
-def add_file_headers(request, media_type, file_size, upload_name):
+def add_file_headers(
+    request: Request,
+    media_type: str,
+    file_size: Optional[int],
+    upload_name: Optional[str],
+) -> None:
     """Adds the correct response headers in preparation for responding with the
     media.
 
     Args:
-        request (twisted.web.http.Request)
-        media_type (str): The media/content type.
-        file_size (int): Size in bytes of the media, if known.
-        upload_name (str): The name of the requested file, if any.
+        request
+        media_type: The media/content type.
+        file_size: Size in bytes of the media, if known.
+        upload_name: The name of the requested file, if any.
     """
 
     def _quote(x):
@@ -153,7 +163,8 @@ def add_file_headers(request, media_type, file_size, upload_name):
     # select private. don't bother setting Expires as all our
     # clients are smart enough to be happy with Cache-Control
     request.setHeader(b"Cache-Control", b"public,max-age=86400,s-maxage=86400")
-    request.setHeader(b"Content-Length", b"%d" % (file_size,))
+    if file_size is not None:
+        request.setHeader(b"Content-Length", b"%d" % (file_size,))
 
     # Tell web crawlers to not index, archive, or follow links in media. This
     # should help to prevent things in the media repo from showing up in web
@@ -184,7 +195,7 @@ _FILENAME_SEPARATOR_CHARS = {
 }
 
 
-def _can_encode_filename_as_token(x):
+def _can_encode_filename_as_token(x: str) -> bool:
     for c in x:
         # from RFC2616:
         #
@@ -206,17 +217,21 @@ def _can_encode_filename_as_token(x):
 
 
 async def respond_with_responder(
-    request, responder, media_type, file_size, upload_name=None
-):
+    request: Request,
+    responder: "Optional[Responder]",
+    media_type: str,
+    file_size: Optional[int],
+    upload_name: Optional[str] = None,
+) -> None:
     """Responds to the request with given responder. If responder is None then
     returns 404.
 
     Args:
-        request (twisted.web.http.Request)
-        responder (Responder|None)
-        media_type (str): The media/content type.
-        file_size (int|None): Size in bytes of the media. If not known it should be None
-        upload_name (str|None): The name of the requested file, if any.
+        request
+        responder
+        media_type: The media/content type.
+        file_size: Size in bytes of the media. If not known it should be None
+        upload_name: The name of the requested file, if any.
     """
     if request._disconnected:
         logger.warning(
@@ -308,22 +323,22 @@ class FileInfo:
         self.thumbnail_type = thumbnail_type
 
 
-def get_filename_from_headers(headers):
+def get_filename_from_headers(headers: Dict[bytes, List[bytes]]) -> Optional[str]:
     """
     Get the filename of the downloaded file by inspecting the
     Content-Disposition HTTP header.
 
     Args:
-        headers (dict[bytes, list[bytes]]): The HTTP request headers.
+        headers: The HTTP request headers.
 
     Returns:
-        A Unicode string of the filename, or None.
+        The filename, or None.
     """
     content_disposition = headers.get(b"Content-Disposition", [b""])
 
     # No header, bail out.
     if not content_disposition[0]:
-        return
+        return None
 
     _, params = _parse_header(content_disposition[0])
 
@@ -356,17 +371,16 @@ def get_filename_from_headers(headers):
     return upload_name
 
 
-def _parse_header(line):
+def _parse_header(line: bytes) -> Tuple[bytes, Dict[bytes, bytes]]:
     """Parse a Content-type like header.
 
     Cargo-culted from `cgi`, but works on bytes rather than strings.
 
     Args:
-        line (bytes): header to be parsed
+        line: header to be parsed
 
     Returns:
-        Tuple[bytes, dict[bytes, bytes]]:
-            the main content-type, followed by the parameter dictionary
+        The main content-type, followed by the parameter dictionary
     """
     parts = _parseparam(b";" + line)
     key = next(parts)
@@ -386,16 +400,16 @@ def _parse_header(line):
     return key, pdict
 
 
-def _parseparam(s):
+def _parseparam(s: bytes) -> Generator[bytes, None, None]:
     """Generator which splits the input on ;, respecting double-quoted sequences
 
     Cargo-culted from `cgi`, but works on bytes rather than strings.
 
     Args:
-        s (bytes): header to be parsed
+        s: header to be parsed
 
     Returns:
-        Iterable[bytes]: the split input
+        The split input
     """
     while s[:1] == b";":
         s = s[1:]
diff --git a/synapse/rest/media/v1/config_resource.py b/synapse/rest/media/v1/config_resource.py
index 68dd2a1c8a..4e4c6971f7 100644
--- a/synapse/rest/media/v1/config_resource.py
+++ b/synapse/rest/media/v1/config_resource.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # Copyright 2018 Will Hunt <will@half-shot.uk>
+# 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.
@@ -14,22 +15,29 @@
 # limitations under the License.
 #
 
+from typing import TYPE_CHECKING
+
+from twisted.web.http import Request
+
 from synapse.http.server import DirectServeJsonResource, respond_with_json
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
+
 
 class MediaConfigResource(DirectServeJsonResource):
     isLeaf = True
 
-    def __init__(self, hs):
+    def __init__(self, hs: "HomeServer"):
         super().__init__()
         config = hs.get_config()
         self.clock = hs.get_clock()
         self.auth = hs.get_auth()
         self.limits_dict = {"m.upload.size": config.max_upload_size}
 
-    async def _async_render_GET(self, request):
+    async def _async_render_GET(self, request: Request) -> None:
         await self.auth.get_user_by_req(request)
         respond_with_json(request, 200, self.limits_dict, send_cors=True)
 
-    async def _async_render_OPTIONS(self, request):
+    async def _async_render_OPTIONS(self, request: Request) -> None:
         respond_with_json(request, 200, {}, send_cors=True)
diff --git a/synapse/rest/media/v1/download_resource.py b/synapse/rest/media/v1/download_resource.py
index d3d8457303..3ed219ae43 100644
--- a/synapse/rest/media/v1/download_resource.py
+++ b/synapse/rest/media/v1/download_resource.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # 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.
@@ -13,24 +14,31 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import logging
+from typing import TYPE_CHECKING
+
+from twisted.web.http import Request
 
-import synapse.http.servlet
 from synapse.http.server import DirectServeJsonResource, set_cors_headers
+from synapse.http.servlet import parse_boolean
 
 from ._base import parse_media_id, respond_404
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
+    from synapse.rest.media.v1.media_repository import MediaRepository
+
 logger = logging.getLogger(__name__)
 
 
 class DownloadResource(DirectServeJsonResource):
     isLeaf = True
 
-    def __init__(self, hs, media_repo):
+    def __init__(self, hs: "HomeServer", media_repo: "MediaRepository"):
         super().__init__()
         self.media_repo = media_repo
         self.server_name = hs.hostname
 
-    async def _async_render_GET(self, request):
+    async def _async_render_GET(self, request: Request) -> None:
         set_cors_headers(request)
         request.setHeader(
             b"Content-Security-Policy",
@@ -49,9 +57,7 @@ class DownloadResource(DirectServeJsonResource):
         if server_name == self.server_name:
             await self.media_repo.get_local_media(request, media_id, name)
         else:
-            allow_remote = synapse.http.servlet.parse_boolean(
-                request, "allow_remote", default=True
-            )
+            allow_remote = parse_boolean(request, "allow_remote", default=True)
             if not allow_remote:
                 logger.info(
                     "Rejecting request for remote media %s/%s due to allow_remote",
diff --git a/synapse/rest/media/v1/filepath.py b/synapse/rest/media/v1/filepath.py
index 9e079f672f..7792f26e78 100644
--- a/synapse/rest/media/v1/filepath.py
+++ b/synapse/rest/media/v1/filepath.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # 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.
@@ -16,11 +17,12 @@
 import functools
 import os
 import re
+from typing import Callable, List
 
 NEW_FORMAT_ID_RE = re.compile(r"^\d\d\d\d-\d\d-\d\d")
 
 
-def _wrap_in_base_path(func):
+def _wrap_in_base_path(func: "Callable[..., str]") -> "Callable[..., str]":
     """Takes a function that returns a relative path and turns it into an
     absolute path based on the location of the primary media store
     """
@@ -41,12 +43,18 @@ class MediaFilePaths:
     to write to the backup media store (when one is configured)
     """
 
-    def __init__(self, primary_base_path):
+    def __init__(self, primary_base_path: str):
         self.base_path = primary_base_path
 
     def default_thumbnail_rel(
-        self, default_top_level, default_sub_type, width, height, content_type, method
-    ):
+        self,
+        default_top_level: str,
+        default_sub_type: str,
+        width: int,
+        height: int,
+        content_type: str,
+        method: str,
+    ) -> str:
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (width, height, top_level_type, sub_type, method)
         return os.path.join(
@@ -55,12 +63,14 @@ class MediaFilePaths:
 
     default_thumbnail = _wrap_in_base_path(default_thumbnail_rel)
 
-    def local_media_filepath_rel(self, media_id):
+    def local_media_filepath_rel(self, media_id: str) -> str:
         return os.path.join("local_content", media_id[0:2], media_id[2:4], media_id[4:])
 
     local_media_filepath = _wrap_in_base_path(local_media_filepath_rel)
 
-    def local_media_thumbnail_rel(self, media_id, width, height, content_type, method):
+    def local_media_thumbnail_rel(
+        self, media_id: str, width: int, height: int, content_type: str, method: str
+    ) -> str:
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (width, height, top_level_type, sub_type, method)
         return os.path.join(
@@ -86,7 +96,7 @@ class MediaFilePaths:
             media_id[4:],
         )
 
-    def remote_media_filepath_rel(self, server_name, file_id):
+    def remote_media_filepath_rel(self, server_name: str, file_id: str) -> str:
         return os.path.join(
             "remote_content", server_name, file_id[0:2], file_id[2:4], file_id[4:]
         )
@@ -94,8 +104,14 @@ class MediaFilePaths:
     remote_media_filepath = _wrap_in_base_path(remote_media_filepath_rel)
 
     def remote_media_thumbnail_rel(
-        self, server_name, file_id, width, height, content_type, method
-    ):
+        self,
+        server_name: str,
+        file_id: str,
+        width: int,
+        height: int,
+        content_type: str,
+        method: str,
+    ) -> str:
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s-%s" % (width, height, top_level_type, sub_type, method)
         return os.path.join(
@@ -113,7 +129,7 @@ class MediaFilePaths:
     # Should be removed after some time, when most of the thumbnails are stored
     # using the new path.
     def remote_media_thumbnail_rel_legacy(
-        self, server_name, file_id, width, height, content_type
+        self, server_name: str, file_id: str, width: int, height: int, content_type: str
     ):
         top_level_type, sub_type = content_type.split("/")
         file_name = "%i-%i-%s-%s" % (width, height, top_level_type, sub_type)
@@ -126,7 +142,7 @@ class MediaFilePaths:
             file_name,
         )
 
-    def remote_media_thumbnail_dir(self, server_name, file_id):
+    def remote_media_thumbnail_dir(self, server_name: str, file_id: str) -> str:
         return os.path.join(
             self.base_path,
             "remote_thumbnail",
@@ -136,7 +152,7 @@ class MediaFilePaths:
             file_id[4:],
         )
 
-    def url_cache_filepath_rel(self, media_id):
+    def url_cache_filepath_rel(self, media_id: str) -> str:
         if NEW_FORMAT_ID_RE.match(media_id):
             # Media id is of the form <DATE><RANDOM_STRING>
             # E.g.: 2017-09-28-fsdRDt24DS234dsf
@@ -146,7 +162,7 @@ class MediaFilePaths:
 
     url_cache_filepath = _wrap_in_base_path(url_cache_filepath_rel)
 
-    def url_cache_filepath_dirs_to_delete(self, media_id):
+    def url_cache_filepath_dirs_to_delete(self, media_id: str) -> List[str]:
         "The dirs to try and remove if we delete the media_id file"
         if NEW_FORMAT_ID_RE.match(media_id):
             return [os.path.join(self.base_path, "url_cache", media_id[:10])]
@@ -156,7 +172,9 @@ class MediaFilePaths:
                 os.path.join(self.base_path, "url_cache", media_id[0:2]),
             ]
 
-    def url_cache_thumbnail_rel(self, media_id, width, height, content_type, method):
+    def url_cache_thumbnail_rel(
+        self, media_id: str, width: int, height: int, content_type: str, method: str
+    ) -> str:
         # Media id is of the form <DATE><RANDOM_STRING>
         # E.g.: 2017-09-28-fsdRDt24DS234dsf
 
@@ -178,7 +196,7 @@ class MediaFilePaths:
 
     url_cache_thumbnail = _wrap_in_base_path(url_cache_thumbnail_rel)
 
-    def url_cache_thumbnail_directory(self, media_id):
+    def url_cache_thumbnail_directory(self, media_id: str) -> str:
         # Media id is of the form <DATE><RANDOM_STRING>
         # E.g.: 2017-09-28-fsdRDt24DS234dsf
 
@@ -195,7 +213,7 @@ class MediaFilePaths:
                 media_id[4:],
             )
 
-    def url_cache_thumbnail_dirs_to_delete(self, media_id):
+    def url_cache_thumbnail_dirs_to_delete(self, media_id: str) -> List[str]:
         "The dirs to try and remove if we delete the media_id thumbnails"
         # Media id is of the form <DATE><RANDOM_STRING>
         # E.g.: 2017-09-28-fsdRDt24DS234dsf
diff --git a/synapse/rest/media/v1/media_repository.py b/synapse/rest/media/v1/media_repository.py
index 83beb02b05..4c9946a616 100644
--- a/synapse/rest/media/v1/media_repository.py
+++ b/synapse/rest/media/v1/media_repository.py
@@ -1,6 +1,6 @@
 # -*- coding: utf-8 -*-
 # Copyright 2014-2016 OpenMarket Ltd
-# Copyright 2018 New Vector Ltd
+# Copyright 2018-2021 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.
@@ -13,12 +13,12 @@
 # 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 errno
 import logging
 import os
 import shutil
-from typing import IO, Dict, List, Optional, Tuple
+from io import BytesIO
+from typing import IO, TYPE_CHECKING, Dict, List, Optional, Set, Tuple
 
 import twisted.internet.error
 import twisted.web.http
@@ -56,6 +56,9 @@ from .thumbnail_resource import ThumbnailResource
 from .thumbnailer import Thumbnailer, ThumbnailError
 from .upload_resource import UploadResource
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
+
 logger = logging.getLogger(__name__)
 
 
@@ -63,7 +66,7 @@ UPDATE_RECENTLY_ACCESSED_TS = 60 * 1000
 
 
 class MediaRepository:
-    def __init__(self, hs):
+    def __init__(self, hs: "HomeServer"):
         self.hs = hs
         self.auth = hs.get_auth()
         self.client = hs.get_federation_http_client()
@@ -73,16 +76,16 @@ class MediaRepository:
         self.max_upload_size = hs.config.max_upload_size
         self.max_image_pixels = hs.config.max_image_pixels
 
-        self.primary_base_path = hs.config.media_store_path
-        self.filepaths = MediaFilePaths(self.primary_base_path)
+        self.primary_base_path = hs.config.media_store_path  # type: str
+        self.filepaths = MediaFilePaths(self.primary_base_path)  # type: MediaFilePaths
 
         self.dynamic_thumbnails = hs.config.dynamic_thumbnails
         self.thumbnail_requirements = hs.config.thumbnail_requirements
 
         self.remote_media_linearizer = Linearizer(name="media_remote")
 
-        self.recently_accessed_remotes = set()
-        self.recently_accessed_locals = set()
+        self.recently_accessed_remotes = set()  # type: Set[Tuple[str, str]]
+        self.recently_accessed_locals = set()  # type: Set[str]
 
         self.federation_domain_whitelist = hs.config.federation_domain_whitelist
 
@@ -113,7 +116,7 @@ class MediaRepository:
             "update_recently_accessed_media", self._update_recently_accessed
         )
 
-    async def _update_recently_accessed(self):
+    async def _update_recently_accessed(self) -> None:
         remote_media = self.recently_accessed_remotes
         self.recently_accessed_remotes = set()
 
@@ -124,12 +127,12 @@ class MediaRepository:
             local_media, remote_media, self.clock.time_msec()
         )
 
-    def mark_recently_accessed(self, server_name, media_id):
+    def mark_recently_accessed(self, server_name: Optional[str], media_id: str) -> None:
         """Mark the given media as recently accessed.
 
         Args:
-            server_name (str|None): Origin server of media, or None if local
-            media_id (str): The media ID of the content
+            server_name: Origin server of media, or None if local
+            media_id: The media ID of the content
         """
         if server_name:
             self.recently_accessed_remotes.add((server_name, media_id))
@@ -459,7 +462,14 @@ class MediaRepository:
     def _get_thumbnail_requirements(self, media_type):
         return self.thumbnail_requirements.get(media_type, ())
 
-    def _generate_thumbnail(self, thumbnailer, t_width, t_height, t_method, t_type):
+    def _generate_thumbnail(
+        self,
+        thumbnailer: Thumbnailer,
+        t_width: int,
+        t_height: int,
+        t_method: str,
+        t_type: str,
+    ) -> Optional[BytesIO]:
         m_width = thumbnailer.width
         m_height = thumbnailer.height
 
@@ -470,22 +480,20 @@ class MediaRepository:
                 m_height,
                 self.max_image_pixels,
             )
-            return
+            return None
 
         if thumbnailer.transpose_method is not None:
             m_width, m_height = thumbnailer.transpose()
 
         if t_method == "crop":
-            t_byte_source = thumbnailer.crop(t_width, t_height, t_type)
+            return thumbnailer.crop(t_width, t_height, t_type)
         elif t_method == "scale":
             t_width, t_height = thumbnailer.aspect(t_width, t_height)
             t_width = min(m_width, t_width)
             t_height = min(m_height, t_height)
-            t_byte_source = thumbnailer.scale(t_width, t_height, t_type)
-        else:
-            t_byte_source = None
+            return thumbnailer.scale(t_width, t_height, t_type)
 
-        return t_byte_source
+        return None
 
     async def generate_local_exact_thumbnail(
         self,
@@ -776,7 +784,7 @@ class MediaRepository:
 
         return {"width": m_width, "height": m_height}
 
-    async def delete_old_remote_media(self, before_ts):
+    async def delete_old_remote_media(self, before_ts: int) -> Dict[str, int]:
         old_media = await self.store.get_remote_media_before(before_ts)
 
         deleted = 0
@@ -928,7 +936,7 @@ class MediaRepositoryResource(Resource):
     within a given rectangle.
     """
 
-    def __init__(self, hs):
+    def __init__(self, hs: "HomeServer"):
         # If we're not configured to use it, raise if we somehow got here.
         if not hs.config.can_load_media_repo:
             raise ConfigError("Synapse is not configured to use a media repo.")
diff --git a/synapse/rest/media/v1/media_storage.py b/synapse/rest/media/v1/media_storage.py
index 268e0c8f50..89cdd605aa 100644
--- a/synapse/rest/media/v1/media_storage.py
+++ b/synapse/rest/media/v1/media_storage.py
@@ -1,5 +1,5 @@
 # -*- coding: utf-8 -*-
-# Copyright 2018 New Vecotr Ltd
+# Copyright 2018-2021 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.
@@ -18,6 +18,8 @@ import os
 import shutil
 from typing import IO, TYPE_CHECKING, Any, Optional, Sequence
 
+from twisted.internet.defer import Deferred
+from twisted.internet.interfaces import IConsumer
 from twisted.protocols.basic import FileSender
 
 from synapse.logging.context import defer_to_thread, make_deferred_yieldable
@@ -270,7 +272,7 @@ class MediaStorage:
         return self.filepaths.local_media_filepath_rel(file_info.file_id)
 
 
-def _write_file_synchronously(source, dest):
+def _write_file_synchronously(source: IO, dest: IO) -> None:
     """Write `source` to the file like `dest` synchronously. Should be called
     from a thread.
 
@@ -286,14 +288,14 @@ class FileResponder(Responder):
     """Wraps an open file that can be sent to a request.
 
     Args:
-        open_file (file): A file like object to be streamed ot the client,
+        open_file: A file like object to be streamed ot the client,
             is closed when finished streaming.
     """
 
-    def __init__(self, open_file):
+    def __init__(self, open_file: IO):
         self.open_file = open_file
 
-    def write_to_consumer(self, consumer):
+    def write_to_consumer(self, consumer: IConsumer) -> Deferred:
         return make_deferred_yieldable(
             FileSender().beginFileTransfer(self.open_file, consumer)
         )
diff --git a/synapse/rest/media/v1/preview_url_resource.py b/synapse/rest/media/v1/preview_url_resource.py
index 1082389d9b..a632099167 100644
--- a/synapse/rest/media/v1/preview_url_resource.py
+++ b/synapse/rest/media/v1/preview_url_resource.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # Copyright 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.
@@ -12,7 +13,6 @@
 # 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 datetime
 import errno
 import fnmatch
@@ -23,12 +23,13 @@ import re
 import shutil
 import sys
 import traceback
-from typing import Dict, Optional
+from typing import TYPE_CHECKING, Any, Dict, Generator, Iterable, Optional, Union
 from urllib import parse as urlparse
 
 import attr
 
 from twisted.internet.error import DNSLookupError
+from twisted.web.http import Request
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.client import SimpleHttpClient
@@ -41,6 +42,7 @@ from synapse.http.servlet import parse_integer, parse_string
 from synapse.logging.context import make_deferred_yieldable, run_in_background
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.rest.media.v1._base import get_filename_from_headers
+from synapse.rest.media.v1.media_storage import MediaStorage
 from synapse.util import json_encoder
 from synapse.util.async_helpers import ObservableDeferred
 from synapse.util.caches.expiringcache import ExpiringCache
@@ -48,6 +50,12 @@ from synapse.util.stringutils import random_string
 
 from ._base import FileInfo
 
+if TYPE_CHECKING:
+    from lxml import etree
+
+    from synapse.app.homeserver import HomeServer
+    from synapse.rest.media.v1.media_repository import MediaRepository
+
 logger = logging.getLogger(__name__)
 
 _charset_match = re.compile(br"<\s*meta[^>]*charset\s*=\s*([a-z0-9-]+)", flags=re.I)
@@ -119,7 +127,12 @@ class OEmbedError(Exception):
 class PreviewUrlResource(DirectServeJsonResource):
     isLeaf = True
 
-    def __init__(self, hs, media_repo, media_storage):
+    def __init__(
+        self,
+        hs: "HomeServer",
+        media_repo: "MediaRepository",
+        media_storage: MediaStorage,
+    ):
         super().__init__()
 
         self.auth = hs.get_auth()
@@ -166,11 +179,11 @@ class PreviewUrlResource(DirectServeJsonResource):
                 self._start_expire_url_cache_data, 10 * 1000
             )
 
-    async def _async_render_OPTIONS(self, request):
+    async def _async_render_OPTIONS(self, request: Request) -> None:
         request.setHeader(b"Allow", b"OPTIONS, GET")
         respond_with_json(request, 200, {}, send_cors=True)
 
-    async def _async_render_GET(self, request):
+    async def _async_render_GET(self, request: Request) -> None:
 
         # XXX: if get_user_by_req fails, what should we do in an async render?
         requester = await self.auth.get_user_by_req(request)
@@ -450,7 +463,7 @@ class PreviewUrlResource(DirectServeJsonResource):
             logger.warning("Error downloading oEmbed metadata from %s: %r", url, e)
             raise OEmbedError() from e
 
-    async def _download_url(self, url: str, user):
+    async def _download_url(self, url: str, user: str) -> Dict[str, Any]:
         # TODO: we should probably honour robots.txt... except in practice
         # we're most likely being explicitly triggered by a human rather than a
         # bot, so are we really a robot?
@@ -580,7 +593,7 @@ class PreviewUrlResource(DirectServeJsonResource):
             "expire_url_cache_data", self._expire_url_cache_data
         )
 
-    async def _expire_url_cache_data(self):
+    async def _expire_url_cache_data(self) -> None:
         """Clean up expired url cache content, media and thumbnails.
         """
         # TODO: Delete from backup media store
@@ -676,7 +689,9 @@ class PreviewUrlResource(DirectServeJsonResource):
             logger.debug("No media removed from url cache")
 
 
-def decode_and_calc_og(body, media_uri, request_encoding=None) -> Dict[str, str]:
+def decode_and_calc_og(
+    body: bytes, media_uri: str, request_encoding: Optional[str] = None
+) -> Dict[str, Optional[str]]:
     # If there's no body, nothing useful is going to be found.
     if not body:
         return {}
@@ -697,7 +712,7 @@ def decode_and_calc_og(body, media_uri, request_encoding=None) -> Dict[str, str]
     return og
 
 
-def _calc_og(tree, media_uri):
+def _calc_og(tree, media_uri: str) -> Dict[str, Optional[str]]:
     # suck our tree into lxml and define our OG response.
 
     # if we see any image URLs in the OG response, then spider them
@@ -801,7 +816,9 @@ def _calc_og(tree, media_uri):
                 for el in _iterate_over_text(tree.find("body"), *TAGS_TO_REMOVE)
             )
             og["og:description"] = summarize_paragraphs(text_nodes)
-    else:
+    elif og["og:description"]:
+        # This must be a non-empty string at this point.
+        assert isinstance(og["og:description"], str)
         og["og:description"] = summarize_paragraphs([og["og:description"]])
 
     # TODO: delete the url downloads to stop diskfilling,
@@ -809,7 +826,9 @@ def _calc_og(tree, media_uri):
     return og
 
 
-def _iterate_over_text(tree, *tags_to_ignore):
+def _iterate_over_text(
+    tree, *tags_to_ignore: Iterable[Union[str, "etree.Comment"]]
+) -> Generator[str, None, None]:
     """Iterate over the tree returning text nodes in a depth first fashion,
     skipping text nodes inside certain tags.
     """
@@ -843,32 +862,32 @@ def _iterate_over_text(tree, *tags_to_ignore):
             )
 
 
-def _rebase_url(url, base):
-    base = list(urlparse.urlparse(base))
-    url = list(urlparse.urlparse(url))
-    if not url[0]:  # fix up schema
-        url[0] = base[0] or "http"
-    if not url[1]:  # fix up hostname
-        url[1] = base[1]
-        if not url[2].startswith("/"):
-            url[2] = re.sub(r"/[^/]+$", "/", base[2]) + url[2]
-    return urlparse.urlunparse(url)
+def _rebase_url(url: str, base: str) -> str:
+    base_parts = list(urlparse.urlparse(base))
+    url_parts = list(urlparse.urlparse(url))
+    if not url_parts[0]:  # fix up schema
+        url_parts[0] = base_parts[0] or "http"
+    if not url_parts[1]:  # fix up hostname
+        url_parts[1] = base_parts[1]
+        if not url_parts[2].startswith("/"):
+            url_parts[2] = re.sub(r"/[^/]+$", "/", base_parts[2]) + url_parts[2]
+    return urlparse.urlunparse(url_parts)
 
 
-def _is_media(content_type):
-    if content_type.lower().startswith("image/"):
-        return True
+def _is_media(content_type: str) -> bool:
+    return content_type.lower().startswith("image/")
 
 
-def _is_html(content_type):
+def _is_html(content_type: str) -> bool:
     content_type = content_type.lower()
-    if content_type.startswith("text/html") or content_type.startswith(
+    return content_type.startswith("text/html") or content_type.startswith(
         "application/xhtml"
-    ):
-        return True
+    )
 
 
-def summarize_paragraphs(text_nodes, min_size=200, max_size=500):
+def summarize_paragraphs(
+    text_nodes: Iterable[str], min_size: int = 200, max_size: int = 500
+) -> Optional[str]:
     # Try to get a summary of between 200 and 500 words, respecting
     # first paragraph and then word boundaries.
     # TODO: Respect sentences?
diff --git a/synapse/rest/media/v1/storage_provider.py b/synapse/rest/media/v1/storage_provider.py
index 67f67efde7..e92006faa9 100644
--- a/synapse/rest/media/v1/storage_provider.py
+++ b/synapse/rest/media/v1/storage_provider.py
@@ -1,5 +1,5 @@
 # -*- coding: utf-8 -*-
-# Copyright 2018 New Vector Ltd
+# Copyright 2018-2021 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.
@@ -13,10 +13,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+import abc
 import logging
 import os
 import shutil
-from typing import Optional
+from typing import TYPE_CHECKING, Optional
 
 from synapse.config._base import Config
 from synapse.logging.context import defer_to_thread, run_in_background
@@ -27,13 +28,17 @@ from .media_storage import FileResponder
 
 logger = logging.getLogger(__name__)
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
 
-class StorageProvider:
+
+class StorageProvider(metaclass=abc.ABCMeta):
     """A storage provider is a service that can store uploaded media and
     retrieve them.
     """
 
-    async def store_file(self, path: str, file_info: FileInfo):
+    @abc.abstractmethod
+    async def store_file(self, path: str, file_info: FileInfo) -> None:
         """Store the file described by file_info. The actual contents can be
         retrieved by reading the file in file_info.upload_path.
 
@@ -42,6 +47,7 @@ class StorageProvider:
             file_info: The metadata of the file.
         """
 
+    @abc.abstractmethod
     async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
         """Attempt to fetch the file described by file_info and stream it
         into writer.
@@ -78,10 +84,10 @@ class StorageProviderWrapper(StorageProvider):
         self.store_synchronous = store_synchronous
         self.store_remote = store_remote
 
-    def __str__(self):
+    def __str__(self) -> str:
         return "StorageProviderWrapper[%s]" % (self.backend,)
 
-    async def store_file(self, path, file_info):
+    async def store_file(self, path: str, file_info: FileInfo) -> None:
         if not file_info.server_name and not self.store_local:
             return None
 
@@ -91,7 +97,7 @@ class StorageProviderWrapper(StorageProvider):
         if self.store_synchronous:
             # store_file is supposed to return an Awaitable, but guard
             # against improper implementations.
-            return await maybe_awaitable(self.backend.store_file(path, file_info))
+            await maybe_awaitable(self.backend.store_file(path, file_info))  # type: ignore
         else:
             # TODO: Handle errors.
             async def store():
@@ -103,9 +109,8 @@ class StorageProviderWrapper(StorageProvider):
                     logger.exception("Error storing file")
 
             run_in_background(store)
-            return None
 
-    async def fetch(self, path, file_info):
+    async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
         # store_file is supposed to return an Awaitable, but guard
         # against improper implementations.
         return await maybe_awaitable(self.backend.fetch(path, file_info))
@@ -115,11 +120,11 @@ class FileStorageProviderBackend(StorageProvider):
     """A storage provider that stores files in a directory on a filesystem.
 
     Args:
-        hs (HomeServer)
+        hs
         config: The config returned by `parse_config`.
     """
 
-    def __init__(self, hs, config):
+    def __init__(self, hs: "HomeServer", config: str):
         self.hs = hs
         self.cache_directory = hs.config.media_store_path
         self.base_directory = config
@@ -127,7 +132,7 @@ class FileStorageProviderBackend(StorageProvider):
     def __str__(self):
         return "FileStorageProviderBackend[%s]" % (self.base_directory,)
 
-    async def store_file(self, path, file_info):
+    async def store_file(self, path: str, file_info: FileInfo) -> None:
         """See StorageProvider.store_file"""
 
         primary_fname = os.path.join(self.cache_directory, path)
@@ -137,19 +142,21 @@ class FileStorageProviderBackend(StorageProvider):
         if not os.path.exists(dirname):
             os.makedirs(dirname)
 
-        return await defer_to_thread(
+        await defer_to_thread(
             self.hs.get_reactor(), shutil.copyfile, primary_fname, backup_fname
         )
 
-    async def fetch(self, path, file_info):
+    async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
         """See StorageProvider.fetch"""
 
         backup_fname = os.path.join(self.base_directory, path)
         if os.path.isfile(backup_fname):
             return FileResponder(open(backup_fname, "rb"))
 
+        return None
+
     @staticmethod
-    def parse_config(config):
+    def parse_config(config: dict) -> str:
         """Called on startup to parse config supplied. This should parse
         the config and raise if there is a problem.
 
diff --git a/synapse/rest/media/v1/thumbnail_resource.py b/synapse/rest/media/v1/thumbnail_resource.py
index 30421b663a..d6880f2e6e 100644
--- a/synapse/rest/media/v1/thumbnail_resource.py
+++ b/synapse/rest/media/v1/thumbnail_resource.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
-# Copyright 2014 - 2016 OpenMarket Ltd
+# 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.
@@ -15,10 +16,14 @@
 
 
 import logging
+from typing import TYPE_CHECKING
+
+from twisted.web.http import Request
 
 from synapse.api.errors import SynapseError
 from synapse.http.server import DirectServeJsonResource, set_cors_headers
 from synapse.http.servlet import parse_integer, parse_string
+from synapse.rest.media.v1.media_storage import MediaStorage
 
 from ._base import (
     FileInfo,
@@ -28,13 +33,22 @@ from ._base import (
     respond_with_responder,
 )
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
+    from synapse.rest.media.v1.media_repository import MediaRepository
+
 logger = logging.getLogger(__name__)
 
 
 class ThumbnailResource(DirectServeJsonResource):
     isLeaf = True
 
-    def __init__(self, hs, media_repo, media_storage):
+    def __init__(
+        self,
+        hs: "HomeServer",
+        media_repo: "MediaRepository",
+        media_storage: MediaStorage,
+    ):
         super().__init__()
 
         self.store = hs.get_datastore()
@@ -43,7 +57,7 @@ class ThumbnailResource(DirectServeJsonResource):
         self.dynamic_thumbnails = hs.config.dynamic_thumbnails
         self.server_name = hs.hostname
 
-    async def _async_render_GET(self, request):
+    async def _async_render_GET(self, request: Request) -> None:
         set_cors_headers(request)
         server_name, media_id, _ = parse_media_id(request)
         width = parse_integer(request, "width", required=True)
@@ -73,8 +87,14 @@ class ThumbnailResource(DirectServeJsonResource):
             self.media_repo.mark_recently_accessed(server_name, media_id)
 
     async def _respond_local_thumbnail(
-        self, request, media_id, width, height, method, m_type
-    ):
+        self,
+        request: Request,
+        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:
@@ -114,13 +134,13 @@ class ThumbnailResource(DirectServeJsonResource):
 
     async def _select_or_generate_local_thumbnail(
         self,
-        request,
-        media_id,
-        desired_width,
-        desired_height,
-        desired_method,
-        desired_type,
-    ):
+        request: Request,
+        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:
@@ -178,14 +198,14 @@ class ThumbnailResource(DirectServeJsonResource):
 
     async def _select_or_generate_remote_thumbnail(
         self,
-        request,
-        server_name,
-        media_id,
-        desired_width,
-        desired_height,
-        desired_method,
-        desired_type,
-    ):
+        request: Request,
+        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(
@@ -239,8 +259,15 @@ class ThumbnailResource(DirectServeJsonResource):
             raise SynapseError(400, "Failed to generate thumbnail.")
 
     async def _respond_remote_thumbnail(
-        self, request, server_name, media_id, width, height, method, m_type
-    ):
+        self,
+        request: Request,
+        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.
@@ -275,12 +302,12 @@ class ThumbnailResource(DirectServeJsonResource):
 
     def _select_thumbnail(
         self,
-        desired_width,
-        desired_height,
-        desired_method,
-        desired_type,
+        desired_width: int,
+        desired_height: int,
+        desired_method: str,
+        desired_type: str,
         thumbnail_infos,
-    ):
+    ) -> dict:
         d_w = desired_width
         d_h = desired_height
 
diff --git a/synapse/rest/media/v1/thumbnailer.py b/synapse/rest/media/v1/thumbnailer.py
index 32a8e4f960..07903e4017 100644
--- a/synapse/rest/media/v1/thumbnailer.py
+++ b/synapse/rest/media/v1/thumbnailer.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # 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.
@@ -14,6 +15,7 @@
 # limitations under the License.
 import logging
 from io import BytesIO
+from typing import Tuple
 
 from PIL import Image
 
@@ -39,7 +41,7 @@ class Thumbnailer:
 
     FORMATS = {"image/jpeg": "JPEG", "image/png": "PNG"}
 
-    def __init__(self, input_path):
+    def __init__(self, input_path: str):
         try:
             self.image = Image.open(input_path)
         except OSError as e:
@@ -59,11 +61,11 @@ class Thumbnailer:
             # A lot of parsing errors can happen when parsing EXIF
             logger.info("Error parsing image EXIF information: %s", e)
 
-    def transpose(self):
+    def transpose(self) -> Tuple[int, int]:
         """Transpose the image using its EXIF Orientation tag
 
         Returns:
-            Tuple[int, int]: (width, height) containing the new image size in pixels.
+            A tuple containing the new image size in pixels as (width, height).
         """
         if self.transpose_method is not None:
             self.image = self.image.transpose(self.transpose_method)
@@ -73,7 +75,7 @@ class Thumbnailer:
             self.image.info["exif"] = None
         return self.image.size
 
-    def aspect(self, max_width, max_height):
+    def aspect(self, max_width: int, max_height: int) -> Tuple[int, int]:
         """Calculate the largest size that preserves aspect ratio which
         fits within the given rectangle::
 
@@ -91,7 +93,7 @@ class Thumbnailer:
         else:
             return (max_height * self.width) // self.height, max_height
 
-    def _resize(self, width, height):
+    def _resize(self, width: int, height: int) -> Image:
         # 1-bit or 8-bit color palette images need converting to RGB
         # otherwise they will be scaled using nearest neighbour which
         # looks awful
@@ -99,7 +101,7 @@ class Thumbnailer:
             self.image = self.image.convert("RGB")
         return self.image.resize((width, height), Image.ANTIALIAS)
 
-    def scale(self, width, height, output_type):
+    def scale(self, width: int, height: int, output_type: str) -> BytesIO:
         """Rescales the image to the given dimensions.
 
         Returns:
@@ -108,7 +110,7 @@ class Thumbnailer:
         scaled = self._resize(width, height)
         return self._encode_image(scaled, output_type)
 
-    def crop(self, width, height, output_type):
+    def crop(self, width: int, height: int, output_type: str) -> BytesIO:
         """Rescales and crops the image to the given dimensions preserving
         aspect::
             (w_in / h_in) = (w_scaled / h_scaled)
@@ -136,7 +138,7 @@ class Thumbnailer:
             cropped = scaled_image.crop((crop_left, 0, crop_right, height))
         return self._encode_image(cropped, output_type)
 
-    def _encode_image(self, output_image, output_type):
+    def _encode_image(self, output_image: Image, output_type: str) -> BytesIO:
         output_bytes_io = BytesIO()
         fmt = self.FORMATS[output_type]
         if fmt == "JPEG":
diff --git a/synapse/rest/media/v1/upload_resource.py b/synapse/rest/media/v1/upload_resource.py
index 42febc9afc..6da76ae994 100644
--- a/synapse/rest/media/v1/upload_resource.py
+++ b/synapse/rest/media/v1/upload_resource.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # 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.
@@ -14,18 +15,25 @@
 # limitations under the License.
 
 import logging
+from typing import TYPE_CHECKING
+
+from twisted.web.http import Request
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.server import DirectServeJsonResource, respond_with_json
 from synapse.http.servlet import parse_string
 
+if TYPE_CHECKING:
+    from synapse.app.homeserver import HomeServer
+    from synapse.rest.media.v1.media_repository import MediaRepository
+
 logger = logging.getLogger(__name__)
 
 
 class UploadResource(DirectServeJsonResource):
     isLeaf = True
 
-    def __init__(self, hs, media_repo):
+    def __init__(self, hs: "HomeServer", media_repo: "MediaRepository"):
         super().__init__()
 
         self.media_repo = media_repo
@@ -37,10 +45,10 @@ class UploadResource(DirectServeJsonResource):
         self.max_upload_size = hs.config.max_upload_size
         self.clock = hs.get_clock()
 
-    async def _async_render_OPTIONS(self, request):
+    async def _async_render_OPTIONS(self, request: Request) -> None:
         respond_with_json(request, 200, {}, send_cors=True)
 
-    async def _async_render_POST(self, request):
+    async def _async_render_POST(self, request: Request) -> None:
         requester = await self.auth.get_user_by_req(request)
         # TODO: The checks here are a bit late. The content will have
         # already been uploaded to a tmp file at this point
diff --git a/synapse/storage/databases/main/media_repository.py b/synapse/storage/databases/main/media_repository.py
index 4b2f224718..283c8a5e22 100644
--- a/synapse/storage/databases/main/media_repository.py
+++ b/synapse/storage/databases/main/media_repository.py
@@ -1,5 +1,6 @@
 # -*- coding: utf-8 -*-
 # 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.
@@ -169,7 +170,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
     async def get_local_media_before(
         self, before_ts: int, size_gt: int, keep_profiles: bool,
-    ) -> Optional[List[str]]:
+    ) -> List[str]:
 
         # to find files that have never been accessed (last_access_ts IS NULL)
         # compare with `created_ts`