diff --git a/protocol/common/message_processor.go b/protocol/common/message_processor.go
index 495e6f715..738b5ca00 100644
--- a/protocol/common/message_processor.go
+++ b/protocol/common/message_processor.go
@@ -160,7 +160,7 @@ func (p *MessageProcessor) sendPrivate(
 
 	messageID := v1protocol.MessageID(&p.identity.PublicKey, wrappedMessage)
 
-	if p.featureFlags.Datasync {
+	if p.featureFlags.Datasync && rawMessage.ResendAutomatically {
 		if err := p.addToDataSync(recipient, wrappedMessage); err != nil {
 			return nil, errors.Wrap(err, "failed to send message with datasync")
 		}
diff --git a/protocol/messenger.go b/protocol/messenger.go
index 7d98ef316..fea068707 100644
--- a/protocol/messenger.go
+++ b/protocol/messenger.go
@@ -1201,10 +1201,11 @@ func (m *Messenger) ReSendChatMessage(ctx context.Context, messageID string) err
 	}
 
 	_, err = m.dispatchMessage(ctx, &common.RawMessage{
-		LocalChatID: chat.ID,
-		Payload:     message.Payload,
-		MessageType: message.MessageType,
-		Recipients:  message.Recipients,
+		LocalChatID:         chat.ID,
+		Payload:             message.Payload,
+		MessageType:         message.MessageType,
+		Recipients:          message.Recipients,
+		ResendAutomatically: message.ResendAutomatically,
 	})
 	return err
 }
@@ -1402,9 +1403,10 @@ func (m *Messenger) SendChatMessage(ctx context.Context, message *Message) (*Mes
 	}
 
 	id, err := m.dispatchMessage(ctx, &common.RawMessage{
-		LocalChatID: chat.ID,
-		Payload:     encodedMessage,
-		MessageType: protobuf.ApplicationMetadataMessage_CHAT_MESSAGE,
+		LocalChatID:         chat.ID,
+		Payload:             encodedMessage,
+		MessageType:         protobuf.ApplicationMetadataMessage_CHAT_MESSAGE,
+		ResendAutomatically: true,
 	})
 	if err != nil {
 		return nil, err