diff --git a/mediaapi/routing/download.go b/mediaapi/routing/download.go
index 3ce4ba395..fa1bb2573 100644
--- a/mediaapi/routing/download.go
+++ b/mediaapi/routing/download.go
@@ -28,6 +28,7 @@ import (
 	"strconv"
 	"strings"
 	"sync"
+	"unicode"
 
 	"github.com/matrix-org/dendrite/clientapi/jsonerror"
 	"github.com/matrix-org/dendrite/internal/config"
@@ -54,6 +55,7 @@ type downloadRequest struct {
 	IsThumbnailRequest bool
 	ThumbnailSize      types.ThumbnailSize
 	Logger             *log.Entry
+	DownloadFilename   string
 }
 
 // Download implements GET /download and GET /thumbnail
@@ -73,6 +75,7 @@ func Download(
 	activeRemoteRequests *types.ActiveRemoteRequests,
 	activeThumbnailGeneration *types.ActiveThumbnailGeneration,
 	isThumbnailRequest bool,
+	customFilename string,
 ) {
 	dReq := &downloadRequest{
 		MediaMetadata: &types.MediaMetadata{
@@ -84,6 +87,7 @@ func Download(
 			"Origin":  origin,
 			"MediaID": mediaID,
 		}),
+		DownloadFilename: customFilename,
 	}
 
 	if dReq.IsThumbnailRequest {
@@ -301,16 +305,8 @@ func (r *downloadRequest) respondFromLocalFile(
 		}).Info("Responding with file")
 		responseFile = file
 		responseMetadata = r.MediaMetadata
-
-		if len(responseMetadata.UploadName) > 0 {
-			uploadName, err := url.PathUnescape(string(responseMetadata.UploadName))
-			if err != nil {
-				return nil, fmt.Errorf("url.PathUnescape: %w", err)
-			}
-			w.Header().Set("Content-Disposition", fmt.Sprintf(
-				`inline; filename=utf-8"%s"`,
-				strings.ReplaceAll(uploadName, `"`, `\"`), // escape quote marks only, as per RFC6266
-			))
+		if err := r.addDownloadFilenameToHeaders(w, responseMetadata); err != nil {
+			return nil, err
 		}
 	}
 
@@ -329,6 +325,67 @@ func (r *downloadRequest) respondFromLocalFile(
 	return responseMetadata, nil
 }
 
+func (r *downloadRequest) addDownloadFilenameToHeaders(
+	w http.ResponseWriter,
+	responseMetadata *types.MediaMetadata,
+) error {
+	// If the requestor supplied a filename to name the download then
+	// use that, otherwise use the filename from the response metadata.
+	filename := string(responseMetadata.UploadName)
+	if r.DownloadFilename != "" {
+		filename = r.DownloadFilename
+	}
+
+	if len(filename) == 0 {
+		return nil
+	}
+
+	unescaped, err := url.PathUnescape(filename)
+	if err != nil {
+		return fmt.Errorf("url.PathUnescape: %w", err)
+	}
+
+	isASCII := true // Is the string ASCII or UTF-8?
+	quote := ``     // Encloses the string (ASCII only)
+	for i := 0; i < len(unescaped); i++ {
+		if unescaped[i] > unicode.MaxASCII {
+			isASCII = false
+		}
+		if unescaped[i] == 0x20 || unescaped[i] == 0x3B {
+			// If the filename contains a space or a semicolon, which
+			// are special characters in Content-Disposition
+			quote = `"`
+		}
+	}
+
+	// We don't necessarily want a full escape as the Content-Disposition
+	// can take many of the characters that PathEscape would otherwise and
+	// browser support for encoding is a bit wild, so we'll escape only
+	// the characters that we know will mess up the parsing of the
+	// Content-Disposition header elements themselves
+	unescaped = strings.ReplaceAll(unescaped, `\`, `\\"`)
+	unescaped = strings.ReplaceAll(unescaped, `"`, `\"`)
+
+	if isASCII {
+		// For ASCII filenames, we should only quote the filename if
+		// it needs to be done, e.g. it contains a space or a character
+		// that would otherwise be parsed as a control character in the
+		// Content-Disposition header
+		w.Header().Set("Content-Disposition", fmt.Sprintf(
+			`inline; filename=%s%s%s`,
+			quote, unescaped, quote,
+		))
+	} else {
+		// For UTF-8 filenames, we quote always, as that's the standard
+		w.Header().Set("Content-Disposition", fmt.Sprintf(
+			`inline; filename=utf-8"%s"`,
+			unescaped,
+		))
+	}
+
+	return nil
+}
+
 // Note: Thumbnail generation may be ongoing asynchronously.
 // If no thumbnail was found then returns nil, nil, nil
 func (r *downloadRequest) getThumbnailFile(
diff --git a/mediaapi/routing/routing.go b/mediaapi/routing/routing.go
index f85778268..bc0de0f45 100644
--- a/mediaapi/routing/routing.go
+++ b/mediaapi/routing/routing.go
@@ -66,7 +66,9 @@ func Setup(
 
 	downloadHandler := makeDownloadAPI("download", cfg, db, client, activeRemoteRequests, activeThumbnailGeneration)
 	r0mux.Handle("/download/{serverName}/{mediaId}", downloadHandler).Methods(http.MethodGet, http.MethodOptions)
-	v1mux.Handle("/download/{serverName}/{mediaId}", downloadHandler).Methods(http.MethodGet, http.MethodOptions) // TODO: remove when synapse is fixed
+	r0mux.Handle("/download/{serverName}/{mediaId}/{downloadName}", downloadHandler).Methods(http.MethodGet, http.MethodOptions)
+	v1mux.Handle("/download/{serverName}/{mediaId}", downloadHandler).Methods(http.MethodGet, http.MethodOptions)                // TODO: remove when synapse is fixed
+	v1mux.Handle("/download/{serverName}/{mediaId}/{downloadName}", downloadHandler).Methods(http.MethodGet, http.MethodOptions) // TODO: remove when synapse is fixed
 
 	r0mux.Handle("/thumbnail/{serverName}/{mediaId}",
 		makeDownloadAPI("thumbnail", cfg, db, client, activeRemoteRequests, activeThumbnailGeneration),
@@ -120,6 +122,7 @@ func makeDownloadAPI(
 			activeRemoteRequests,
 			activeThumbnailGeneration,
 			name == "thumbnail",
+			vars["downloadName"],
 		)
 	}
 	return promhttp.InstrumentHandlerCounter(counterVec, http.HandlerFunc(httpHandler))
diff --git a/mediaapi/routing/upload.go b/mediaapi/routing/upload.go
index 022f978d6..9b5dc3df8 100644
--- a/mediaapi/routing/upload.go
+++ b/mediaapi/routing/upload.go
@@ -16,6 +16,7 @@ package routing
 
 import (
 	"context"
+	"encoding/base64"
 	"fmt"
 	"io"
 	"net/http"
@@ -123,7 +124,9 @@ func (r *uploadRequest) doUpload(
 
 	r.MediaMetadata.FileSizeBytes = bytesWritten
 	r.MediaMetadata.Base64Hash = hash
-	r.MediaMetadata.MediaID = types.MediaID(hash)
+	r.MediaMetadata.MediaID = types.MediaID(base64.RawURLEncoding.EncodeToString(
+		[]byte(string(r.MediaMetadata.UploadName) + string(r.MediaMetadata.Base64Hash)),
+	))
 
 	r.Logger = r.Logger.WithField("MediaID", r.MediaMetadata.MediaID)
 
diff --git a/sytest-whitelist b/sytest-whitelist
index 04c6f0984..8f3d128d7 100644
--- a/sytest-whitelist
+++ b/sytest-whitelist
@@ -128,7 +128,7 @@ Outbound federation can send events
 # test for now.
 #Backfill checks the events requested belong to the room
 Can upload without a file name
-#Can download without a file name locally
+Can download without a file name locally
 Can upload with ASCII file name
 Can send image in room message
 AS cannot create users outside its own namespace
@@ -327,3 +327,7 @@ Can upload with Unicode file name
 POSTed media can be thumbnailed
 Remote media can be thumbnailed
 Can download with Unicode file name locally
+Can download file 'ascii'
+Can download file 'name with spaces'
+Can download file 'name;with;semicolons'
+Can download specifying a different ASCII file name