diff --git a/matrix_appservice_kakaotalk/user.py b/matrix_appservice_kakaotalk/user.py
index 22632c2..0078c72 100644
--- a/matrix_appservice_kakaotalk/user.py
+++ b/matrix_appservice_kakaotalk/user.py
@@ -426,7 +426,16 @@ class User(DBUser, BaseUser):
         sync_count = num_channels if sync_count < 0 else min(sync_count, num_channels)
         await self.push_bridge_state(BridgeStateEvent.BACKFILLING)
         self.log.debug(f"Syncing {sync_count} of {num_channels} channels...")
-        for login_data in login_result.channelList[:sync_count]:
+
+        def get_channel_update_time(login_data: LoginDataItem):
+            channel_info = login_data.channel.info
+            return channel_info.lastChatLog.sendAt if channel_info.lastChatLog else 0
+
+        for login_data in sorted(
+            login_result.channelList,
+            reverse=True,
+            key=get_channel_update_time
+        )[:sync_count]:
             try:
                 await self._sync_channel(login_data)
             except AuthenticationRequired: