diff --git a/lib/pangea/constants/bot_mode.dart b/lib/pangea/constants/bot_mode.dart
index 96aa51e72..fbdd24b6f 100644
--- a/lib/pangea/constants/bot_mode.dart
+++ b/lib/pangea/constants/bot_mode.dart
@@ -1,4 +1,5 @@
 class BotMode {
+  static const direct = "direct";
   static const discussion = "discussion";
   static const custom = "custom";
   static const storyGame = "story_game";
diff --git a/lib/pangea/controllers/pangea_controller.dart b/lib/pangea/controllers/pangea_controller.dart
index 87552955f..fbb23845c 100644
--- a/lib/pangea/controllers/pangea_controller.dart
+++ b/lib/pangea/controllers/pangea_controller.dart
@@ -20,7 +20,6 @@ import 'package:fluffychat/pangea/controllers/subscription_controller.dart';
 import 'package:fluffychat/pangea/controllers/text_to_speech_controller.dart';
 import 'package:fluffychat/pangea/controllers/user_controller.dart';
 import 'package:fluffychat/pangea/controllers/word_net_controller.dart';
-import 'package:fluffychat/pangea/extensions/client_extension/client_extension.dart';
 import 'package:fluffychat/pangea/extensions/pangea_room_extension/pangea_room_extension.dart';
 import 'package:fluffychat/pangea/guard/p_vguard.dart';
 import 'package:fluffychat/pangea/utils/bot_name.dart';
@@ -193,19 +192,53 @@ class PangeaController {
   void startChatWithBotIfNotPresent() {
     Future.delayed(const Duration(milliseconds: 10000), () async {
       // check if user is logged in
-      if (!matrixState.client.isLogged() ||
-          (await matrixState.client.hasBotDM)) {
+      if (!matrixState.client.isLogged()) {
         return;
       }
 
-      try {
-        await matrixState.client.startDirectChat(
-          BotName.byEnvironment,
-          enableEncryption: false,
-        );
-      } catch (err, stack) {
-        debugger(when: kDebugMode);
-        ErrorHandler.logError(e: err, s: stack);
+      const List<Room> botDMs = [];
+      for (final room in matrixState.client.rooms) {
+        if (await room.isBotDM) {
+          botDMs.add(room);
+        }
+      }
+
+      if (botDMs.isEmpty) {
+        try {
+          await matrixState.client.startDirectChat(
+            BotName.byEnvironment,
+            enableEncryption: false,
+          );
+        } catch (err, stack) {
+          debugger(when: kDebugMode);
+          ErrorHandler.logError(e: err, s: stack);
+        }
+        return;
+      }
+
+      final Room botDMWithLatestActivity = botDMs.reduce((a, b) {
+        if (a.timeline == null || b.timeline == null) {
+          return a;
+        }
+        final aLastEvent = a.timeline!.events.last;
+        final bLastEvent = b.timeline!.events.last;
+        return aLastEvent.originServerTs.isAfter(bLastEvent.originServerTs)
+            ? a
+            : b;
+      });
+
+      for (final room in botDMs) {
+        if (room.id != botDMWithLatestActivity.id) {
+          await room.leave();
+          continue;
+        }
+      }
+
+      final participants = await botDMWithLatestActivity.requestParticipants();
+      final joinedParticipants =
+          participants.where((e) => e.membership == Membership.join).toList();
+      if (joinedParticipants.length < 2) {
+        await botDMWithLatestActivity.invite(BotName.byEnvironment);
       }
     });
   }
diff --git a/lib/pangea/extensions/pangea_room_extension/pangea_room_extension.dart b/lib/pangea/extensions/pangea_room_extension/pangea_room_extension.dart
index bf9e10953..813fb7f1c 100644
--- a/lib/pangea/extensions/pangea_room_extension/pangea_room_extension.dart
+++ b/lib/pangea/extensions/pangea_room_extension/pangea_room_extension.dart
@@ -4,6 +4,7 @@ import 'dart:developer';
 
 import 'package:adaptive_dialog/adaptive_dialog.dart';
 import 'package:collection/collection.dart';
+import 'package:fluffychat/pangea/constants/bot_mode.dart';
 import 'package:fluffychat/pangea/constants/class_default_values.dart';
 import 'package:fluffychat/pangea/constants/language_constants.dart';
 import 'package:fluffychat/pangea/constants/model_keys.dart';
@@ -253,7 +254,7 @@ extension PangeaRoom on Room {
 
   // bool isMadeForLang(String langCode) => _isMadeForLang(langCode);
 
-  Future<bool> get isBotRoom async => await _isBotRoom;
+  Future<bool> get botIsInRoom async => await _botIsInRoom;
 
   Future<bool> get isBotDM async => await _isBotDM;
 
diff --git a/lib/pangea/extensions/pangea_room_extension/room_information_extension.dart b/lib/pangea/extensions/pangea_room_extension/room_information_extension.dart
index 857ac26e0..a88551336 100644
--- a/lib/pangea/extensions/pangea_room_extension/room_information_extension.dart
+++ b/lib/pangea/extensions/pangea_room_extension/room_information_extension.dart
@@ -49,15 +49,14 @@ extension RoomInformationRoomExtension on Room {
   //       creationContent?.tryGet<String>(ModelKey.oldLangCode) == langCode;
   // }
 
-  Future<bool> get _isBotRoom async {
+  Future<bool> get _botIsInRoom async {
     final List<User> participants = await requestParticipants();
     return participants.any(
       (User user) => user.id == BotName.byEnvironment,
     );
   }
 
-  Future<bool> get _isBotDM async =>
-      (await isBotRoom) && getParticipants().length == 2;
+  Future<bool> get _isBotDM async => botOptions?.mode == BotMode.direct;
 
   bool get _isLocked {
     if (isDirectChat) return false;
diff --git a/lib/pangea/widgets/conversation_bot/conversation_bot_settings.dart b/lib/pangea/widgets/conversation_bot/conversation_bot_settings.dart
index 288149d76..fe85b48c7 100644
--- a/lib/pangea/widgets/conversation_bot/conversation_bot_settings.dart
+++ b/lib/pangea/widgets/conversation_bot/conversation_bot_settings.dart
@@ -46,7 +46,7 @@ class ConversationBotSettingsState extends State<ConversationBotSettings> {
     botOptions = widget.room?.botOptions != null
         ? BotOptionsModel.fromJson(widget.room?.botOptions?.toJson())
         : BotOptionsModel();
-    widget.room?.isBotRoom.then((bool isBotRoom) {
+    widget.room?.botIsInRoom.then((bool isBotRoom) {
       setState(() {
         addBot = isBotRoom;
       });
@@ -260,7 +260,7 @@ class ConversationBotSettingsState extends State<ConversationBotSettings> {
                         botOptions = botOptions;
                       });
                       final bool isBotRoomMember =
-                          await widget.room?.isBotRoom ?? false;
+                          await widget.room?.botIsInRoom ?? false;
                       if (addBot && !isBotRoomMember) {
                         await widget.room?.invite(BotName.byEnvironment);
                       } else if (!addBot && isBotRoomMember) {