diff --git a/database/mediabackfillrequest.go b/database/mediabackfillrequest.go
index 45a5245..d8a6cb5 100644
--- a/database/mediabackfillrequest.go
+++ b/database/mediabackfillrequest.go
@@ -45,6 +45,7 @@ type MediaBackfillRequest struct {
 	UserID    id.UserID
 	PortalKey *PortalKey
 	EventID   id.EventID
+	MediaKey  []byte
 	Status    MediaBackfillRequestStatus
 	Error     string
 }
@@ -57,20 +58,21 @@ func (mbrq *MediaBackfillRequestQuery) newMediaBackfillRequest() *MediaBackfillR
 	}
 }
 
-func (mbrq *MediaBackfillRequestQuery) NewMediaBackfillRequestWithValues(userID id.UserID, portalKey *PortalKey, eventID id.EventID) *MediaBackfillRequest {
+func (mbrq *MediaBackfillRequestQuery) NewMediaBackfillRequestWithValues(userID id.UserID, portalKey *PortalKey, eventID id.EventID, mediaKey []byte) *MediaBackfillRequest {
 	return &MediaBackfillRequest{
 		db:        mbrq.db,
 		log:       mbrq.log,
 		UserID:    userID,
 		PortalKey: portalKey,
 		EventID:   eventID,
+		MediaKey:  mediaKey,
 		Status:    MediaBackfillRequestStatusNotRequested,
 	}
 }
 
 const (
 	getMediaBackfillRequestsForUser = `
-		SELECT user_mxid, portal_jid, portal_receiver, event_id, status, error
+		SELECT user_mxid, portal_jid, portal_receiver, event_id, media_key, status, error
 		FROM media_backfill_requests
 		WHERE user_mxid=$1
 			AND status=0
@@ -79,17 +81,18 @@ const (
 
 func (mbr *MediaBackfillRequest) Upsert() {
 	_, err := mbr.db.Exec(`
-		INSERT INTO media_backfill_requests (user_mxid, portal_jid, portal_receiver, event_id, status, error)
-		VALUES ($1, $2, $3, $4, $5, $6)
+		INSERT INTO media_backfill_requests (user_mxid, portal_jid, portal_receiver, event_id, media_key, status, error)
+		VALUES ($1, $2, $3, $4, $5, $6, $7)
 		ON CONFLICT (user_mxid, portal_jid, portal_receiver, event_id)
 		DO UPDATE SET
+			media_key=EXCLUDED.media_key,
 			status=EXCLUDED.status,
-			error=EXCLUDED.error
-	`,
+			error=EXCLUDED.error`,
 		mbr.UserID,
 		mbr.PortalKey.JID.String(),
 		mbr.PortalKey.Receiver.String(),
 		mbr.EventID,
+		mbr.MediaKey,
 		mbr.Status,
 		mbr.Error)
 	if err != nil {
@@ -98,7 +101,7 @@ func (mbr *MediaBackfillRequest) Upsert() {
 }
 
 func (mbr *MediaBackfillRequest) Scan(row Scannable) *MediaBackfillRequest {
-	err := row.Scan(&mbr.UserID, &mbr.PortalKey.JID, &mbr.PortalKey.Receiver, &mbr.EventID, &mbr.Status, &mbr.Error)
+	err := row.Scan(&mbr.UserID, &mbr.PortalKey.JID, &mbr.PortalKey.Receiver, &mbr.EventID, &mbr.MediaKey, &mbr.Status, &mbr.Error)
 	if err != nil {
 		if !errors.Is(err, sql.ErrNoRows) {
 			mbr.log.Errorln("Database scan failed:", err)
diff --git a/database/upgrades/2022-05-09-media-backfill-requests-queue-table.go b/database/upgrades/2022-05-09-media-backfill-requests-queue-table.go
index 5cfa6e4..2470ffa 100644
--- a/database/upgrades/2022-05-09-media-backfill-requests-queue-table.go
+++ b/database/upgrades/2022-05-09-media-backfill-requests-queue-table.go
@@ -12,6 +12,7 @@ func init() {
 				portal_jid          TEXT,
 				portal_receiver     TEXT,
 				event_id            TEXT,
+				media_key           BYTEA,
 				status              INTEGER,
 				error               TEXT,
 
diff --git a/historysync.go b/historysync.go
index 9bf9266..fed28d8 100644
--- a/historysync.go
+++ b/historysync.go
@@ -112,7 +112,7 @@ func (user *User) dailyMediaRequestLoop() {
 		// Send all of the media backfill requests for the user at once
 		for _, req := range mediaBackfillRequests {
 			portal := user.GetPortalByJID(req.PortalKey.JID)
-			_, err := portal.requestMediaRetry(user, req.EventID)
+			_, err := portal.requestMediaRetry(user, req.EventID, req.MediaKey)
 			if err != nil {
 				user.log.Warnf("Failed to send media retry request for %s / %s", req.PortalKey.String(), req.EventID)
 				req.Status = database.MediaBackfillRequestStatusRequestFailed
@@ -121,6 +121,7 @@ func (user *User) dailyMediaRequestLoop() {
 				user.log.Debugfln("Sent media retry request for %s / %s", req.PortalKey.String(), req.EventID)
 				req.Status = database.MediaBackfillRequestStatusRequested
 			}
+			req.MediaKey = nil
 			req.Upsert()
 		}
 
@@ -588,7 +589,7 @@ func (portal *Portal) requestMediaRetries(source *User, eventIDs []id.EventID, i
 					portal.log.Debugfln("Sent post-backfill media retry request for %s", info.ID)
 				}
 			case config.MediaRequestMethodLocalTime:
-				req := portal.bridge.DB.MediaBackfillRequest.NewMediaBackfillRequestWithValues(source.MXID, &portal.Key, eventIDs[i])
+				req := portal.bridge.DB.MediaBackfillRequest.NewMediaBackfillRequestWithValues(source.MXID, &portal.Key, eventIDs[i], info.MediaKey)
 				req.Upsert()
 			}
 		}
diff --git a/matrix.go b/matrix.go
index 90309a1..2b9f899 100644
--- a/matrix.go
+++ b/matrix.go
@@ -491,7 +491,7 @@ func (mx *MatrixHandler) HandleReaction(evt *event.Event) {
 
 	content := evt.Content.AsReaction()
 	if strings.Contains(content.RelatesTo.Key, "retry") || strings.HasPrefix(content.RelatesTo.Key, "\u267b") { // ♻️
-		if retryRequested, _ := portal.requestMediaRetry(user, content.RelatesTo.EventID); retryRequested {
+		if retryRequested, _ := portal.requestMediaRetry(user, content.RelatesTo.EventID, nil); retryRequested {
 			_, _ = portal.MainIntent().RedactEvent(portal.MXID, evt.ID, mautrix.ReqRedact{
 				Reason: "requested media from phone",
 			})
diff --git a/portal.go b/portal.go
index b791eae..4759c6b 100644
--- a/portal.go
+++ b/portal.go
@@ -2346,7 +2346,7 @@ func (portal *Portal) handleMediaRetry(retry *events.MediaRetry, source *User) {
 	msg.UpdateMXID(resp.EventID, database.MsgNormal, database.MsgNoError)
 }
 
-func (portal *Portal) requestMediaRetry(user *User, eventID id.EventID) (bool, error) {
+func (portal *Portal) requestMediaRetry(user *User, eventID id.EventID, mediaKey []byte) (bool, error) {
 	msg := portal.bridge.DB.Message.GetByMXID(eventID)
 	if msg == nil {
 		err := errors.New(fmt.Sprintf("%s requested a media retry for unknown event %s", user.MXID, eventID))
@@ -2358,13 +2358,17 @@ func (portal *Portal) requestMediaRetry(user *User, eventID id.EventID) (bool, e
 		return false, err
 	}
 
-	evt, err := portal.fetchMediaRetryEvent(msg)
-	if err != nil {
-		portal.log.Warnfln("Can't send media retry request for %s: %v", msg.JID, err)
-		return true, nil
+	// If the media key is not provided, grab it from the event in Matrix
+	if mediaKey == nil {
+		evt, err := portal.fetchMediaRetryEvent(msg)
+		if err != nil {
+			portal.log.Warnfln("Can't send media retry request for %s: %v", msg.JID, err)
+			return true, nil
+		}
+		mediaKey = evt.Media.Key
 	}
 
-	err = user.Client.SendMediaRetryReceipt(&types.MessageInfo{
+	err := user.Client.SendMediaRetryReceipt(&types.MessageInfo{
 		ID: msg.JID,
 		MessageSource: types.MessageSource{
 			IsFromMe: msg.Sender.User == user.JID.User,
@@ -2372,7 +2376,7 @@ func (portal *Portal) requestMediaRetry(user *User, eventID id.EventID) (bool, e
 			Sender:   msg.Sender,
 			Chat:     portal.Key.JID,
 		},
-	}, evt.Media.Key)
+	}, mediaKey)
 	if err != nil {
 		portal.log.Warnfln("Failed to send media retry request for %s: %v", msg.JID, err)
 	} else {