diff --git a/lib/pangea/bot/utils/bot_room_extension.dart b/lib/pangea/bot/utils/bot_room_extension.dart
index b658235ed..830ca6a84 100644
--- a/lib/pangea/bot/utils/bot_room_extension.dart
+++ b/lib/pangea/bot/utils/bot_room_extension.dart
@@ -3,6 +3,7 @@ import 'package:matrix/matrix.dart';
 import 'package:fluffychat/pangea/bot/utils/bot_name.dart';
 import 'package:fluffychat/pangea/chat_settings/constants/bot_mode.dart';
 import 'package:fluffychat/pangea/chat_settings/models/bot_options_model.dart';
+import 'package:fluffychat/pangea/common/utils/error_handler.dart';
 import 'package:fluffychat/pangea/events/constants/pangea_event_types.dart';
 
 extension BotRoomExtension on Room {
@@ -23,11 +24,40 @@ extension BotRoomExtension on Room {
     return BotOptionsModel.fromJson(stateEvent.content);
   }
 
-  Future<void> setBotOptions(BotOptionsModel options) =>
-      client.setRoomStateWithKey(
-        id,
-        PangeaEventTypes.botOptions,
-        '',
-        options.toJson(),
-      );
+  Future<void> setBotOptions(BotOptionsModel options) async {
+    const maxRetries = 3;
+    Duration retryDelay = const Duration(seconds: 5);
+
+    for (int attempt = 1; attempt <= maxRetries; attempt++) {
+      try {
+        if (attempt > 1) {
+          await Future.delayed(retryDelay);
+          retryDelay *= 2;
+        }
+
+        await client.setRoomStateWithKey(
+          id,
+          PangeaEventTypes.botOptions,
+          '',
+          options.toJson(),
+        );
+
+        return;
+      } catch (e, s) {
+        ErrorHandler.logError(
+          e: e,
+          s: s,
+          data: {
+            'roomId': id,
+            'options': options.toJson(),
+            'attempt': attempt,
+          },
+        );
+
+        if (attempt == maxRetries) {
+          rethrow;
+        }
+      }
+    }
+  }
 }
diff --git a/lib/pangea/chat_settings/utils/bot_client_extension.dart b/lib/pangea/chat_settings/utils/bot_client_extension.dart
index 5021d19ed..69c9b84cc 100644
--- a/lib/pangea/chat_settings/utils/bot_client_extension.dart
+++ b/lib/pangea/chat_settings/utils/bot_client_extension.dart
@@ -1,11 +1,13 @@
 import 'package:collection/collection.dart';
 import 'package:matrix/matrix.dart';
 
+import 'package:fluffychat/pangea/activity_sessions/activity_room_extension.dart';
 import 'package:fluffychat/pangea/bot/utils/bot_name.dart';
 import 'package:fluffychat/pangea/bot/utils/bot_room_extension.dart';
 import 'package:fluffychat/pangea/chat/constants/default_power_level.dart';
 import 'package:fluffychat/pangea/chat_settings/constants/bot_mode.dart';
 import 'package:fluffychat/pangea/chat_settings/models/bot_options_model.dart';
+import 'package:fluffychat/pangea/common/utils/error_handler.dart';
 import 'package:fluffychat/pangea/events/constants/pangea_event_types.dart';
 import 'package:fluffychat/pangea/user/user_model.dart';
 import 'package:fluffychat/widgets/matrix.dart';
@@ -15,10 +17,15 @@ extension BotClientExtension on Client {
   Room? get botDM => rooms.firstWhereOrNull((r) => r.isBotDM);
 
   // All 2-member rooms with the bot
-  List<Room> get targetBotChats => rooms.where((r) {
-        if (r.isBotDM) return true;
-        if (r.summary.mJoinedMemberCount != 2) return false;
-        return r.getParticipants().any((u) => u.id == BotName.byEnvironment);
+  List<Room> get _targetBotChats => rooms.where((r) {
+        return
+            // bot settings exist
+            r.botOptions != null &&
+                // there is no activity plan
+                r.activityPlan == null &&
+                // it's just the bot and one other user in the room
+                r.summary.mJoinedMemberCount == 2 &&
+                r.getParticipants().any((u) => u.id == BotName.byEnvironment);
       }).toList();
 
   Future<String> startChatWithBot() => startDirectChat(
@@ -42,30 +49,41 @@ extension BotClientExtension on Client {
       );
 
   Future<void> updateBotOptions(UserSettings userSettings) async {
-    final rooms = targetBotChats;
-    if (rooms.isEmpty) return;
+    final targetBotRooms = [..._targetBotChats];
+    if (targetBotRooms.isEmpty) return;
 
-    final futures = <Future>[];
-    for (final room in rooms) {
-      final botOptions = room.botOptions ?? const BotOptionsModel();
-      final targetLanguage = userSettings.targetLanguage;
-      final languageLevel = userSettings.cefrLevel;
-      final voice = userSettings.voice;
+    try {
+      final futures = <Future>[];
+      for (final targetBotRoom in targetBotRooms) {
+        final botOptions = targetBotRoom.botOptions ?? const BotOptionsModel();
+        final targetLanguage = userSettings.targetLanguage;
+        final languageLevel = userSettings.cefrLevel;
+        final voice = userSettings.voice;
 
-      if (botOptions.targetLanguage == targetLanguage &&
-          botOptions.languageLevel == languageLevel &&
-          botOptions.targetVoice == voice) {
-        continue;
+        if (botOptions.targetLanguage == targetLanguage &&
+            botOptions.languageLevel == languageLevel &&
+            botOptions.targetVoice == voice) {
+          continue;
+        }
+
+        final updated = botOptions.copyWith(
+          targetLanguage: targetLanguage,
+          languageLevel: languageLevel,
+          targetVoice: voice,
+        );
+        futures.add(targetBotRoom.setBotOptions(updated));
       }
 
-      final updated = botOptions.copyWith(
-        targetLanguage: targetLanguage,
-        languageLevel: languageLevel,
-        targetVoice: voice,
+      await Future.wait(futures);
+    } catch (e, s) {
+      ErrorHandler.logError(
+        e: e,
+        s: s,
+        data: {
+          'userSettings': userSettings.toJson(),
+          'targetBotRooms': targetBotRooms.map((r) => r.id).toList(),
+        },
       );
-      futures.add(room.setBotOptions(updated));
     }
-
-    await Future.wait(futures);
   }
 }