diff --git a/pkg/connector/backfill.go b/pkg/connector/backfill.go
index 6a1e99ad..dd8783ee 100644
--- a/pkg/connector/backfill.go
+++ b/pkg/connector/backfill.go
@@ -279,7 +279,7 @@ func (t *TelegramClient) FetchMessages(ctx context.Context, fetchParams bridgev2
 
 		sender := t.getEventSender(message, !portal.Metadata.(*PortalMetadata).IsSuperGroup)
 		intent := portal.GetIntentFor(ctx, sender, t.userLogin, bridgev2.RemoteEventBackfill)
-		converted, err := t.convertToMatrix(ctx, portal, intent, message)
+		converted, err := t.convertToMatrixWithRefetch(ctx, portal, intent, message)
 		if err != nil {
 			return nil, err
 		}
diff --git a/pkg/connector/telegram.go b/pkg/connector/telegram.go
index 7cfa3502..e76f3ecc 100644
--- a/pkg/connector/telegram.go
+++ b/pkg/connector/telegram.go
@@ -146,7 +146,7 @@ func (t *TelegramClient) onUpdateNewMessage(ctx context.Context, entities tg.Ent
 			},
 			ID:                 ids.GetMessageIDFromMessage(msg),
 			Data:               msg,
-			ConvertMessageFunc: t.convertToMatrix,
+			ConvertMessageFunc: t.convertToMatrixWithRefetch,
 		})
 	case *tg.MessageService:
 		sender := t.getEventSender(msg, false)
@@ -766,7 +766,7 @@ func (t *TelegramClient) onMessageEdit(ctx context.Context, update IGetMessage)
 		Data:          msg,
 		ConvertEditFunc: func(ctx context.Context, portal *bridgev2.Portal, intent bridgev2.MatrixAPI, existing []*database.Message, data *tg.Message) (*bridgev2.ConvertedEdit, error) {
 			log := zerolog.Ctx(ctx)
-			converted, err := t.convertToMatrix(ctx, portal, intent, msg)
+			converted, err := t.convertToMatrixWithRefetch(ctx, portal, intent, msg)
 			if err != nil {
 				return nil, err
 			}
diff --git a/pkg/connector/tomatrix.go b/pkg/connector/tomatrix.go
index 714c4082..40e25a57 100644
--- a/pkg/connector/tomatrix.go
+++ b/pkg/connector/tomatrix.go
@@ -10,6 +10,7 @@ import (
 	"time"
 
 	"github.com/gotd/td/tg"
+	"github.com/gotd/td/tgerr"
 	"github.com/rs/zerolog"
 	"go.mau.fi/util/exmime"
 	"go.mau.fi/util/ptr"
@@ -102,6 +103,36 @@ func (c *TelegramClient) mediaToMatrix(ctx context.Context, portal *bridgev2.Por
 	}
 }
 
+func (c *TelegramClient) convertToMatrixWithRefetch(ctx context.Context, portal *bridgev2.Portal, intent bridgev2.MatrixAPI, msg *tg.Message) (cm *bridgev2.ConvertedMessage, err error) {
+	cm, err = c.convertToMatrix(ctx, portal, intent, msg)
+	if !tgerr.Is(err, tg.ErrFileReferenceExpired) {
+		return cm, err
+	}
+
+	// If the error is that the file reference expired, refetch the message and
+	// try to convert it again.
+	log := zerolog.Ctx(ctx).With().Bool("message_refetch", true).Logger()
+	ctx = log.WithContext(ctx)
+	log.Warn().Err(err).Msg("Refetching message to convert media")
+
+	m, err := c.client.API().MessagesGetMessages(ctx, []tg.InputMessageClass{
+		&tg.InputMessageID{ID: msg.ID},
+	})
+	if err != nil {
+		return nil, err
+	} else if messages, ok := m.(tg.ModifiedMessagesMessages); !ok {
+		return nil, fmt.Errorf("unsupported messages type %T", messages)
+	} else if len(messages.GetMessages()) != 1 {
+		return nil, fmt.Errorf("wrong number of messages retrieved %d", len(messages.GetMessages()))
+	} else if refetchedMsg, ok := messages.GetMessages()[0].(*tg.Message); !ok {
+		return nil, fmt.Errorf("message was of the wrong type %s", messages.GetMessages()[0].TypeName())
+	} else if refetchedMsg.ID != msg.ID {
+		return nil, fmt.Errorf("no media found with ID %d", msg.ID)
+	} else {
+		return c.convertToMatrix(ctx, portal, intent, refetchedMsg)
+	}
+}
+
 func (c *TelegramClient) convertToMatrix(ctx context.Context, portal *bridgev2.Portal, intent bridgev2.MatrixAPI, msg *tg.Message) (cm *bridgev2.ConvertedMessage, err error) {
 	log := zerolog.Ctx(ctx).With().Str("conversion_direction", "to_matrix").Logger()
 	ctx = log.WithContext(ctx)