diff --git a/receiving.cpp b/receiving.cpp
index 3f69e13..a5f62d9 100644
--- a/receiving.cpp
+++ b/receiving.cpp
@@ -1056,7 +1056,7 @@ void handleIncomingMessage(TdAccountData &account, const td::td_api::chat &chat,
 static void fetchHistoryRequest(TdAccountData &account, ChatId chatId, unsigned messagesFetched,
                                 MessageId fetchBackFrom, MessageId lastReceivedMessage);
 
-static void fetchHistoryResponse(TdAccountData &account, ChatId chatId, MessageId lastReceivedMessage,
+static void fetchHistoryResponse(TdAccountData &account, ChatId chatId, MessageId stopAt,
                                  unsigned messagesFetched,
                                  td::td_api::object_ptr<td::td_api::Object> response)
 {
@@ -1075,12 +1075,12 @@ static void fetchHistoryResponse(TdAccountData &account, ChatId chatId, MessageI
                 purple_debug_warning(config::pluginId, "Erroneous message in history, stopping\n");
                 break;
             }
-            if (lastReceivedMessage.valid() && (getId(*message) == lastReceivedMessage)) {
+            if (stopAt.valid() && (getId(*message) == stopAt)) {
                 purple_debug_misc(config::pluginId, "Found message %" G_GINT64_FORMAT ", stopping\n",
-                                  lastReceivedMessage.value());
+                                  stopAt.value());
                 break;
             }
-            if ((!lastReceivedMessage.valid() && (messagesFetched == 100)) ||
+            if ((!stopAt.valid() && (messagesFetched == 100)) ||
                 (messagesFetched == HISTORY_MESSAGES_ABSOLUTE_LIMIT))
             {
                 purple_debug_misc(config::pluginId, "Reached history limit, stopping\n");
@@ -1103,7 +1103,7 @@ static void fetchHistoryResponse(TdAccountData &account, ChatId chatId, MessageI
     }
 
     if (requestMoreFrom.valid())
-        fetchHistoryRequest(account, chatId, messagesFetched, requestMoreFrom, lastReceivedMessage);
+        fetchHistoryRequest(account, chatId, messagesFetched, requestMoreFrom, stopAt);
     else {
         purple_debug_misc(config::pluginId, "Done fetching history for chat %" G_GINT64_FORMAT "\n",
                           chatId.value());
@@ -1114,7 +1114,7 @@ static void fetchHistoryResponse(TdAccountData &account, ChatId chatId, MessageI
 }
 
 static void fetchHistoryRequest(TdAccountData &account, ChatId chatId, unsigned messagesFetched,
-                                MessageId fetchBackFrom, MessageId lastReceivedMessage)
+                                MessageId fetchBackFrom, MessageId stopAt)
 {
     auto request = td::td_api::make_object<td::td_api::getChatHistory>();
     request->chat_id_ = chatId.value();
@@ -1125,16 +1125,16 @@ static void fetchHistoryRequest(TdAccountData &account, ChatId chatId, unsigned
     purple_debug_misc(config::pluginId, "Requesting history for chat %" G_GINT64_FORMAT
                       " starting from %" G_GINT64_FORMAT "\n", chatId.value(), fetchBackFrom.value());
     account.transceiver.sendQuery(std::move(request),
-        [&account, chatId, messagesFetched, lastReceivedMessage](uint64_t requestId, td::td_api::object_ptr<td::td_api::Object> response) {
-            fetchHistoryResponse(account, chatId, lastReceivedMessage, messagesFetched, std::move(response));
+        [&account, chatId, messagesFetched, stopAt](uint64_t requestId, td::td_api::object_ptr<td::td_api::Object> response) {
+            fetchHistoryResponse(account, chatId, stopAt, messagesFetched, std::move(response));
         });
 }
 
-void fetchHistory(TdAccountData &account, ChatId chatId, MessageId lastReceivedMessage)
+void fetchHistory(TdAccountData &account, ChatId chatId, MessageId fetchFrom, MessageId stopAt)
 {
     if (!account.pendingMessages.isChatReady(chatId))
         return;
 
     account.pendingMessages.setChatNotReady(chatId);
-    fetchHistoryRequest(account, chatId, 0, MessageId::invalid, lastReceivedMessage);
+    fetchHistoryRequest(account, chatId, 0, fetchFrom, stopAt);
 }
diff --git a/receiving.h b/receiving.h
index eedf2d4..5c7454d 100644
--- a/receiving.h
+++ b/receiving.h
@@ -53,7 +53,7 @@ void checkMessageReady(const IncomingMessage *message, TdTransceiver &transceive
 void handleIncomingMessage(TdAccountData &account, const td::td_api::chat &chat,
                            td::td_api::object_ptr<td::td_api::message> message,
                            PendingMessageQueue::MessageAction action);
-void fetchHistory(TdAccountData &account, ChatId chatId, MessageId lastReceivedMessage);
+void fetchHistory(TdAccountData &account, ChatId chatId, MessageId fetchFrom, MessageId stopAt);
 
 #endif
 
diff --git a/td-client.cpp b/td-client.cpp
index 5221a74..807a57d 100644
--- a/td-client.cpp
+++ b/td-client.cpp
@@ -173,19 +173,7 @@ void PurpleTdClient::processUpdate(td::td_api::Object &update)
 
     case td::td_api::updateChatLastMessage::ID: {
         auto &lastMessage = static_cast<td::td_api::updateChatLastMessage &>(update);
-        ChatId chatId = getChatId(lastMessage);
-        m_data.updateChatOrder(chatId, lastMessage.order_);
-        if (lastMessage.last_message_)
-            saveChatLastMessage(m_data, chatId, getId(*lastMessage.last_message_));
-        else {
-            MessageId lastMessageId = getChatLastMessage(m_data, chatId);
-            if (lastMessageId.valid()) {
-                purple_debug_misc(config::pluginId, "Skipped messages detected for chat %" G_GINT64_FORMAT
-                                  ", fetching history until %" G_GINT64_FORMAT "\n",
-                                  chatId.value(), lastMessageId.value());
-                fetchHistory(m_data, chatId, lastMessageId);
-            }
-        }
+        updateChatLastMessage(lastMessage);
         break;
     }
 
@@ -943,8 +931,20 @@ void PurpleTdClient::onIncomingMessage(td::td_api::object_ptr<td::td_api::messag
 {
     if (!message)
         return;
-
     ChatId chatId = getChatId(*message);
+
+    auto pGap = std::find_if(m_chatGaps.begin(), m_chatGaps.end(),
+                             [chatId](const ChatGap &gap) { return (gap.chatId == chatId); });
+    if (pGap != m_chatGaps.end()) {
+        MessageId lastMessageId = pGap->lastMessage;
+        m_chatGaps.erase(pGap);
+        purple_debug_misc(config::pluginId,
+            "Fetching skipped messages for chat %" G_GINT64_FORMAT
+            " between %" G_GINT64_FORMAT " and %" G_GINT64_FORMAT "\n",
+            chatId.value(), lastMessageId.value(), getId(*message).value());
+        fetchHistory(m_data, chatId, getId(*message), lastMessageId);
+    }
+
     const td::td_api::chat *chat = m_data.getChat(chatId);
     if (!chat) {
         purple_debug_warning(config::pluginId, "Received message with unknown chat id %" G_GINT64_FORMAT "\n",
@@ -955,6 +955,31 @@ void PurpleTdClient::onIncomingMessage(td::td_api::object_ptr<td::td_api::messag
     handleIncomingMessage(m_data, *chat, std::move(message), PendingMessageQueue::Append);
 }
 
+void PurpleTdClient::updateChatLastMessage(const td::td_api::updateChatLastMessage &lastMessage)
+{
+    ChatId chatId = getChatId(lastMessage);
+    m_data.updateChatOrder(chatId, lastMessage.order_);
+    if (lastMessage.last_message_)
+        saveChatLastMessage(m_data, chatId, getId(*lastMessage.last_message_));
+    else {
+        MessageId lastMessageId = getChatLastMessage(m_data, chatId);
+        if (lastMessageId.valid()) {
+            purple_debug_misc(config::pluginId,
+                "Skipped messages detected for chat %" G_GINT64_FORMAT
+                ", last seen message %" G_GINT64_FORMAT "\n",
+                chatId.value(), lastMessageId.value());
+            if (std::find_if(m_chatGaps.begin(), m_chatGaps.end(),
+                             [chatId](const ChatGap &gap) {
+                                 return (gap.chatId == chatId);
+                             }) == m_chatGaps.end()) {
+                m_chatGaps.emplace_back();
+                m_chatGaps.back().chatId = chatId;
+                m_chatGaps.back().lastMessage = lastMessageId;
+            }
+        }
+    }
+}
+
 int PurpleTdClient::sendMessage(const char *buddyName, const char *message)
 {
     SecretChatId secretChatId           = purpleBuddyNameToSecretChatId(buddyName);
diff --git a/td-client.h b/td-client.h
index 0242a96..496ae81 100644
--- a/td-client.h
+++ b/td-client.h
@@ -90,8 +90,7 @@ private:
     // Login sequence end
 
     void       onIncomingMessage(td::td_api::object_ptr<td::td_api::message> message);
-    void       findMessageResponse(ChatId chatId, MessageId pendingMessageId,
-                                   td::td_api::object_ptr<td::td_api::Object> object);
+    void       updateChatLastMessage(const td::td_api::updateChatLastMessage &lastMessage);
 
     void       updateUserStatus(UserId userId, td::td_api::object_ptr<td::td_api::UserStatus> status);
     void       updateUser(td::td_api::object_ptr<td::td_api::user> user);
@@ -150,6 +149,12 @@ private:
     std::vector<PurpleRoomlist *>               m_pendingRoomLists;
     td::td_api::object_ptr<td::td_api::proxy>   m_addedProxy;
     td::td_api::object_ptr<td::td_api::proxies> m_proxies;
+
+    struct ChatGap {
+        ChatId    chatId;
+        MessageId lastMessage;
+    };
+    std::vector<ChatGap> m_chatGaps;
 };
 
 #endif
diff --git a/test/message-history-test.cpp b/test/message-history-test.cpp
index c0c47c0..35514ca 100644
--- a/test/message-history-test.cpp
+++ b/test/message-history-test.cpp
@@ -24,11 +24,11 @@ TEST_F(MessageHistoryTest, TdlibSkipMessages)
     tgl.update(make_object<updateChatLastMessage>(
         groupChatId, nullptr, 0
     ));
-    tgl.verifyRequest(getChatHistory(groupChatId, 0, 0, 30, false));
 
     tgl.update(make_object<updateNewMessage>(
         makeMessage(6, userIds[0], groupChatId, false, 6, makeTextMessage("6"))
     ));
+    tgl.verifyRequest(getChatHistory(groupChatId, 6, 0, 30, false));
     tgl.update(make_object<updateChatLastMessage>(
         groupChatId,
         makeMessage(6, userIds[0], groupChatId, false, 6, makeTextMessage("6")),
@@ -72,7 +72,20 @@ TEST_F(MessageHistoryTest, TdlibSkipMessages)
     );
     tgl.verifyRequest(viewMessages(groupChatId, {6, 7, 5, 4, 3, 2}, true));
 
-    ASSERT_EQ(std::string("7"), std::string(purple_account_get_string(
+    tgl.update(make_object<updateNewMessage>(
+        makeMessage(8, userIds[0], groupChatId, false, 8, makeTextMessage("8"))
+    ));
+    tgl.update(make_object<updateChatLastMessage>(
+        groupChatId,
+        makeMessage(8, userIds[0], groupChatId, false, 8, makeTextMessage("8")),
+        0
+    ));
+    prpl.verifyEvents(
+        ServGotChatEvent(connection, purpleChatId, userNameInChat, "8", PURPLE_MESSAGE_RECV, 8)
+    );
+    tgl.verifyRequest(viewMessages(groupChatId, {8}, true));
+
+    ASSERT_EQ(std::string("8"), std::string(purple_account_get_string(
         account, ("last-message-chat" + std::to_string(groupChatId)).c_str(), "")));
 }
 
@@ -85,11 +98,11 @@ TEST_F(MessageHistoryTest, TdlibSkipMessages_FlushAtLogout)
     tgl.update(make_object<updateChatLastMessage>(
         groupChatId, nullptr, 0
     ));
-    tgl.verifyRequest(getChatHistory(groupChatId, 0, 0, 30, false));
 
     tgl.update(make_object<updateNewMessage>(
         makeMessage(6, userIds[0], groupChatId, false, 6, makeTextMessage("6"))
     ));
+    tgl.verifyRequest(getChatHistory(groupChatId, 6, 0, 30, false));
     tgl.update(make_object<updateChatLastMessage>(
         groupChatId,
         makeMessage(6, userIds[0], groupChatId, false, 6, makeTextMessage("6")),