diff --git a/go.mod b/go.mod
index 3da557325..cb912be3b 100644
--- a/go.mod
+++ b/go.mod
@@ -17,7 +17,7 @@ require (
 	github.com/matrix-org/go-http-js-libp2p v0.0.0-20200318135427-31631a9ef51f
 	github.com/matrix-org/go-sqlite3-js v0.0.0-20200325174927-327088cdef10
 	github.com/matrix-org/gomatrix v0.0.0-20190528120928-7df988a63f26
-	github.com/matrix-org/gomatrixserverlib v0.0.0-20200507150553-025991c971ea
+	github.com/matrix-org/gomatrixserverlib v0.0.0-20200511150133-f4a8869b5366
 	github.com/matrix-org/naffka v0.0.0-20200422140631-181f1ee7401f
 	github.com/matrix-org/util v0.0.0-20190711121626-527ce5ddefc7
 	github.com/mattn/go-sqlite3 v2.0.2+incompatible
diff --git a/go.sum b/go.sum
index 871648069..a6f160052 100644
--- a/go.sum
+++ b/go.sum
@@ -367,8 +367,8 @@ github.com/matrix-org/gomatrix v0.0.0-20190528120928-7df988a63f26 h1:Hr3zjRsq2bh
 github.com/matrix-org/gomatrix v0.0.0-20190528120928-7df988a63f26/go.mod h1:3fxX6gUjWyI/2Bt7J1OLhpCzOfO/bB3AiX0cJtEKud0=
 github.com/matrix-org/gomatrixserverlib v0.0.0-20200124100636-0c2ec91d1df5 h1:kmRjpmFOenVpOaV/DRlo9p6z/IbOKlUC+hhKsAAh8Qg=
 github.com/matrix-org/gomatrixserverlib v0.0.0-20200124100636-0c2ec91d1df5/go.mod h1:FsKa2pWE/bpQql9H7U4boOPXFoJX/QcqaZZ6ijLkaZI=
-github.com/matrix-org/gomatrixserverlib v0.0.0-20200507150553-025991c971ea h1:1qfbSjg3PwULY68AVRdZ3QIJoccNMbre0mSR7m7mqI4=
-github.com/matrix-org/gomatrixserverlib v0.0.0-20200507150553-025991c971ea/go.mod h1:JsAzE1Ll3+gDWS9JSUHPJiiyAksvOOnGWF2nXdg4ZzU=
+github.com/matrix-org/gomatrixserverlib v0.0.0-20200511150133-f4a8869b5366 h1:LbtCldIuE/kEgGnzKm6xebnZDfDie1vQA0mDq7ReyM4=
+github.com/matrix-org/gomatrixserverlib v0.0.0-20200511150133-f4a8869b5366/go.mod h1:JsAzE1Ll3+gDWS9JSUHPJiiyAksvOOnGWF2nXdg4ZzU=
 github.com/matrix-org/naffka v0.0.0-20200127221512-0716baaabaf1 h1:osLoFdOy+ChQqVUn2PeTDETFftVkl4w9t/OW18g3lnk=
 github.com/matrix-org/naffka v0.0.0-20200127221512-0716baaabaf1/go.mod h1:cXoYQIENbdWIQHt1SyCo6Bl3C3raHwJ0wgVrXHSqf+A=
 github.com/matrix-org/naffka v0.0.0-20200422140631-181f1ee7401f h1:pRz4VTiRCO4zPlEMc3ESdUOcW4PXHH4Kj+YDz1XyE+Y=
diff --git a/mediaapi/routing/download.go b/mediaapi/routing/download.go
index 8544bd64f..9feca90e9 100644
--- a/mediaapi/routing/download.go
+++ b/mediaapi/routing/download.go
@@ -118,7 +118,10 @@ func Download(
 	)
 	if err != nil {
 		// TODO: Handle the fact we might have started writing the response
-		dReq.jsonErrorResponse(w, util.ErrorResponse(err))
+		dReq.jsonErrorResponse(w, util.JSONResponse{
+			Code: http.StatusNotFound,
+			JSON: jsonerror.NotFound("Failed to download: " + err.Error()),
+		})
 		return
 	}
 
@@ -138,7 +141,7 @@ func (r *downloadRequest) jsonErrorResponse(w http.ResponseWriter, res util.JSON
 	if err != nil {
 		r.Logger.WithError(err).Error("Failed to marshal JSONResponse")
 		// this should never fail to be marshalled so drop err to the floor
-		res = util.MessageResponse(http.StatusInternalServerError, "Internal Server Error")
+		res = util.MessageResponse(http.StatusNotFound, "Download request failed: "+err.Error())
 		resBytes, _ = json.Marshal(res.JSON)
 	}
 
diff --git a/sytest-whitelist b/sytest-whitelist
index c957021cb..6e1b4f631 100644
--- a/sytest-whitelist
+++ b/sytest-whitelist
@@ -264,3 +264,4 @@ User can invite local user to room with version 5
 remote user can join room with version 5
 User can invite remote user to room with version 5
 Remote user can backfill in a room with version 5
+Alternative server names do not cause a routing loop