diff --git a/AUTHORS.rst b/AUTHORS.rst
index fd3513fd..9d720d19 100644
--- a/AUTHORS.rst
+++ b/AUTHORS.rst
@@ -86,4 +86,5 @@ Source Contributors
 - cmays90 `@cmays90 <https://github.com/cmays90>`_
 - Dio Brando `@isFakeAccount <https://github.com/isFakeAccount>`_
 - Josh Kim `@jsk56143 <https://github.com/jsk56143>`_
+- Rolf Campbell `@endlisnis <https://github.com/endlisnis>`_
 - Add "Name <email (optional)> and github profile link" above this line.
diff --git a/asyncpraw/models/reddit/subreddit.py b/asyncpraw/models/reddit/subreddit.py
index 5c36ee6d..3ae18b0b 100644
--- a/asyncpraw/models/reddit/subreddit.py
+++ b/asyncpraw/models/reddit/subreddit.py
@@ -24,8 +24,10 @@
 from xml.etree.ElementTree import XML
 
 from aiohttp import ClientResponse
+from aiohttp.http_exceptions import HttpProcessingError
 from aiohttp.web_ws import WebSocketError
 from asyncprawcore import Redirect
+from asyncprawcore.exceptions import ServerError
 
 from ...const import API_PATH, JPEG_HEADER
 from ...exceptions import (
@@ -692,6 +694,13 @@ async def _submit_media(self, data: dict, timeout: int, websocket_url: str = Non
             url = ws_update["payload"]["redirect"]
             return await self._reddit.submission(url=url)
 
+    async def _read_and_post_media(self, media_path, upload_url, upload_data):
+        with open(media_path, "rb") as media:
+            response = await self._reddit._core._requestor._http.post(
+                upload_url, data=upload_data, files={"file": media}
+            )
+        return response
+
     async def _upload_media(
         self,
         media_path: str,
@@ -744,14 +753,13 @@ async def _upload_media(
         upload_url = f"https:{upload_lease['action']}"
         upload_data = {item["name"]: item["value"] for item in upload_lease["fields"]}
 
-        with open(media_path, "rb") as media:
-            upload_data["file"] = media
-            response = await self._reddit._core._requestor._http.post(
-                upload_url, data=upload_data
-            )
+        response = await self._read_and_post_media(media_path, upload_url, upload_data)
         if not response.status == 201:
             self._parse_xml_response(response)
-        response.raise_for_status()
+        try:
+            response.raise_for_status()
+        except HttpProcessingError:
+            raise ServerError(response=response)
 
         websocket_url = upload_response["asset"]["websocket_url"]
 
diff --git a/tests/unit/models/reddit/test_subreddit.py b/tests/unit/models/reddit/test_subreddit.py
index 6b9bce7e..968d5453 100644
--- a/tests/unit/models/reddit/test_subreddit.py
+++ b/tests/unit/models/reddit/test_subreddit.py
@@ -71,13 +71,36 @@ async def test_invalid_media(self, connection_mock, _mock_upload_media, _mock_po
         context_manager.__aenter__.return_value = recv_mock
         connection_mock.return_value = context_manager
 
-        # websockets_mock().__aenter__.recv =
         with pytest.raises(MediaPostFailed):
             await Subreddit(self.reddit, display_name="test").submit_image(
                 "Test", "dummy path"
             )
         await self.reddit._core._requestor._http.close()
 
+    @mock.patch("asyncpraw.models.Subreddit._read_and_post_media")
+    @mock.patch(
+        "asyncpraw.Reddit.post",
+        return_value={
+            "json": {"data": {"websocket_url": ""}},
+            "args": {"action": "", "fields": []},
+        },
+    )
+    @mock.patch("aiohttp.client.ClientSession.ws_connect")
+    async def test_media_upload_500(self, connection_mock, _mock_post, mock_method):
+        from aiohttp.http_exceptions import HttpProcessingError
+        from asyncprawcore.exceptions import ServerError
+
+        response = mock.Mock()
+        response.status = 201
+        response.raise_for_status = mock.Mock(
+            side_effect=HttpProcessingError(code=500, message="")
+        )
+        mock_method.return_value = response
+        with pytest.raises(ServerError):
+            await Subreddit(self.reddit, display_name="test").submit_image(
+                "Test", "/dev/null"
+            )
+
     def test_repr(self):
         subreddit = Subreddit(self.reddit, display_name="name")
         assert repr(subreddit) == "Subreddit(display_name='name')"