diff --git a/src/core/error/response.rs b/src/core/error/response.rs
index c41d542c..41cfa72d 100644
--- a/src/core/error/response.rs
+++ b/src/core/error/response.rs
@@ -60,6 +60,9 @@ pub(super) fn bad_request_code(kind: &ErrorKind) -> StatusCode {
 		// 429
 		| LimitExceeded { .. } => StatusCode::TOO_MANY_REQUESTS,
 
+		// 409
+		| CannotOverwriteMedia => StatusCode::CONFLICT,
+
 		// 413
 		| TooLarge => StatusCode::PAYLOAD_TOO_LARGE,
 
@@ -69,6 +72,9 @@ pub(super) fn bad_request_code(kind: &ErrorKind) -> StatusCode {
 		// 404
 		| NotFound | NotImplemented | FeatureDisabled => StatusCode::NOT_FOUND,
 
+		// 504
+		| NotYetUploaded => StatusCode::GATEWAY_TIMEOUT,
+
 		// 403
 		| GuestAccessForbidden
 		| ThreepidAuthFailed
diff --git a/src/service/media/mod.rs b/src/service/media/mod.rs
index 81cd2987..9a84a29c 100644
--- a/src/service/media/mod.rs
+++ b/src/service/media/mod.rs
@@ -159,6 +159,10 @@ impl Service {
 	) -> Result<()> {
 		let pending = self.db.search_pending_mxc(mxc).await;
 		let Some((owner_id, expires_at)) = pending else {
+			if self.get_metadata(mxc).await.is_some() {
+				return Err!(Request(CannotOverwriteMedia("Media ID already has content")));
+			}
+
 			return Err!(Request(NotFound("Media not found")));
 		};
 
diff --git a/tests/complement/results.jsonl b/tests/complement/results.jsonl
index 810bb021..8b6bb70b 100644
--- a/tests/complement/results.jsonl
+++ b/tests/complement/results.jsonl
@@ -9,13 +9,13 @@
 {"Action":"pass","Test":"TestArchivedRoomsHistory/timeline_is_empty"}
 {"Action":"skip","Test":"TestArchivedRoomsHistory/timeline_is_empty/incremental_sync"}
 {"Action":"pass","Test":"TestArchivedRoomsHistory/timeline_is_empty/initial_sync"}
-{"Action":"fail","Test":"TestAsyncUpload"}
-{"Action":"fail","Test":"TestAsyncUpload/Cannot_upload_to_a_media_ID_that_has_already_been_uploaded_to"}
-{"Action":"fail","Test":"TestAsyncUpload/Create_media"}
-{"Action":"fail","Test":"TestAsyncUpload/Download_media"}
-{"Action":"fail","Test":"TestAsyncUpload/Download_media_over__matrix/client/v1/media/download"}
-{"Action":"fail","Test":"TestAsyncUpload/Not_yet_uploaded"}
-{"Action":"fail","Test":"TestAsyncUpload/Upload_media"}
+{"Action":"pass","Test":"TestAsyncUpload"}
+{"Action":"pass","Test":"TestAsyncUpload/Cannot_upload_to_a_media_ID_that_has_already_been_uploaded_to"}
+{"Action":"pass","Test":"TestAsyncUpload/Create_media"}
+{"Action":"pass","Test":"TestAsyncUpload/Download_media"}
+{"Action":"pass","Test":"TestAsyncUpload/Download_media_over__matrix/client/v1/media/download"}
+{"Action":"pass","Test":"TestAsyncUpload/Not_yet_uploaded"}
+{"Action":"pass","Test":"TestAsyncUpload/Upload_media"}
 {"Action":"pass","Test":"TestAvatarUrlUpdate"}
 {"Action":"pass","Test":"TestBannedUserCannotSendJoin"}
 {"Action":"skip","Test":"TestCanRegisterAdmin"}