diff --git a/lib/pages/chat/events/html_message.dart b/lib/pages/chat/events/html_message.dart
index 393a1fa46..67263af7b 100644
--- a/lib/pages/chat/events/html_message.dart
+++ b/lib/pages/chat/events/html_message.dart
@@ -14,7 +14,7 @@ import 'package:fluffychat/pages/chat/chat.dart';
 import 'package:fluffychat/pangea/events/event_wrappers/pangea_message_event.dart';
 import 'package:fluffychat/pangea/events/models/pangea_token_model.dart';
 import 'package:fluffychat/pangea/message_token_text/message_token_button.dart';
-import 'package:fluffychat/pangea/message_token_text/token_position_model.dart';
+import 'package:fluffychat/pangea/message_token_text/tokens_util.dart';
 import 'package:fluffychat/pangea/toolbar/enums/reading_assistance_mode_enum.dart';
 import 'package:fluffychat/pangea/toolbar/utils/token_rendering_util.dart';
 import 'package:fluffychat/pangea/toolbar/widgets/message_selection_overlay.dart';
@@ -396,6 +396,9 @@ class HtmlMessage extends StatelessWidget {
     );
 
     final fontSize = renderer.fontSize(context) ?? this.fontSize;
+    final newTokens = pangeaMessageEvent != null
+        ? TokensUtil.getNewTokens(pangeaMessageEvent!)
+        : [];
     // Pangea#
 
     switch (node.localName) {
@@ -415,10 +418,7 @@ class HtmlMessage extends StatelessWidget {
             ? isHighlighted!.call(token)
             : false;
 
-        final isNew = token != null &&
-            overlayController != null &&
-            overlayController!.isNewToken(token);
-
+        final isNew = token != null && newTokens.contains(token.text);
         final tokenWidth = renderer.tokenTextWidthForContainer(
           context,
           node.text,
diff --git a/lib/pangea/course_plans/course_plan_builder.dart b/lib/pangea/course_plans/course_plan_builder.dart
index 8618dcaa1..e83847b02 100644
--- a/lib/pangea/course_plans/course_plan_builder.dart
+++ b/lib/pangea/course_plans/course_plan_builder.dart
@@ -68,9 +68,7 @@ class CoursePlanController extends State<CoursePlanBuilder> {
       widget.onNotFound?.call();
       error = e;
     } finally {
-      setState(() {
-        loading = false;
-      });
+      if (mounted) setState(() => loading = false);
     }
   }
 
diff --git a/lib/pangea/message_token_text/token_position_model.dart b/lib/pangea/message_token_text/tokens_util.dart
similarity index 69%
rename from lib/pangea/message_token_text/token_position_model.dart
rename to lib/pangea/message_token_text/tokens_util.dart
index cd5a47355..1922f656d 100644
--- a/lib/pangea/message_token_text/token_position_model.dart
+++ b/lib/pangea/message_token_text/tokens_util.dart
@@ -1,4 +1,27 @@
+import 'package:fluffychat/pangea/events/event_wrappers/pangea_message_event.dart';
 import 'package:fluffychat/pangea/events/models/pangea_token_model.dart';
+import 'package:fluffychat/pangea/events/models/pangea_token_text_model.dart';
+import 'package:fluffychat/widgets/matrix.dart';
+
+class _TokenPositionCacheItem {
+  final List<TokenPosition> positions;
+  final DateTime timestamp;
+
+  _TokenPositionCacheItem(
+    this.positions,
+    this.timestamp,
+  );
+}
+
+class _NewTokenCacheItem {
+  final List<PangeaTokenText> tokens;
+  final DateTime timestamp;
+
+  _NewTokenCacheItem(
+    this.tokens,
+    this.timestamp,
+  );
+}
 
 class TokenPosition {
   final PangeaToken? token;
@@ -15,9 +38,74 @@ class TokenPosition {
 class TokensUtil {
   /// A cache of calculated adjacent token positions
   static final Map<String, _TokenPositionCacheItem> _tokenPositionCache = {};
+  static final Map<String, _NewTokenCacheItem> _newTokenCache = {};
 
   static const Duration _cacheDuration = Duration(minutes: 1);
 
+  static List<PangeaTokenText>? _getCachedNewTokens(String eventID) {
+    final cacheItem = _newTokenCache[eventID];
+    if (cacheItem == null) return null;
+    if (cacheItem.timestamp.isBefore(DateTime.now().subtract(_cacheDuration))) {
+      _newTokenCache.remove(eventID);
+      return null;
+    }
+
+    return cacheItem.tokens;
+  }
+
+  static void _setCachedNewTokens(
+    String eventID,
+    List<PangeaTokenText> tokens,
+  ) {
+    _newTokenCache[eventID] = _NewTokenCacheItem(
+      tokens,
+      DateTime.now(),
+    );
+  }
+
+  static List<PangeaTokenText> getNewTokens(
+    PangeaMessageEvent event,
+  ) {
+    final messageInUserL2 = event.messageDisplayLangCode.split("-")[0] ==
+        MatrixState.pangeaController.languageController.userL2?.langCodeShort;
+
+    final cached = _getCachedNewTokens(event.eventId);
+    if (cached != null) {
+      if (!messageInUserL2) {
+        _newTokenCache.remove(event.eventId);
+        return [];
+      }
+      return cached;
+    }
+
+    final tokens = event.messageDisplayRepresentation?.tokens;
+    if (!messageInUserL2 || tokens == null || tokens.isEmpty) {
+      return [];
+    }
+
+    final List<PangeaTokenText> newTokens = [];
+    for (final token in tokens) {
+      if (!token.lemma.saveVocab || !token.isContentWord) continue;
+      if (token.vocabConstruct.uses.isNotEmpty) continue;
+      if (newTokens.any((t) => t == token.text)) continue;
+
+      newTokens.add(token.text);
+      if (newTokens.length >= 3) break;
+    }
+
+    _setCachedNewTokens(event.eventId, newTokens);
+    return newTokens;
+  }
+
+  static bool isNewToken(PangeaToken token, PangeaMessageEvent event) {
+    final newTokens = getNewTokens(event);
+    return newTokens.any((t) => t == token.text);
+  }
+
+  static clearNewTokenCache(String eventID) {
+    _newTokenCache.remove(eventID);
+  }
+
   static List<TokenPosition>? _getCachedTokenPositions(String eventID) {
     final cacheItem = _tokenPositionCache[eventID];
     if (cacheItem == null) return null;
@@ -158,13 +246,3 @@ class TokensUtil {
     return tokenPositions;
   }
 }
-
-class _TokenPositionCacheItem {
-  final List<TokenPosition> positions;
-  final DateTime timestamp;
-
-  _TokenPositionCacheItem(
-    this.positions,
-    this.timestamp,
-  );
-}
diff --git a/lib/pangea/toolbar/widgets/message_selection_overlay.dart b/lib/pangea/toolbar/widgets/message_selection_overlay.dart
index 43bcbb1dd..ddd0f5c64 100644
--- a/lib/pangea/toolbar/widgets/message_selection_overlay.dart
+++ b/lib/pangea/toolbar/widgets/message_selection_overlay.dart
@@ -19,6 +19,7 @@ import 'package:fluffychat/pangea/events/event_wrappers/pangea_message_event.dar
 import 'package:fluffychat/pangea/events/event_wrappers/pangea_representation_event.dart';
 import 'package:fluffychat/pangea/events/models/pangea_token_model.dart';
 import 'package:fluffychat/pangea/events/models/pangea_token_text_model.dart';
+import 'package:fluffychat/pangea/message_token_text/tokens_util.dart';
 import 'package:fluffychat/pangea/practice_activities/activity_type_enum.dart';
 import 'package:fluffychat/pangea/practice_activities/practice_activity_model.dart';
 import 'package:fluffychat/pangea/practice_activities/practice_choice.dart';
@@ -102,8 +103,6 @@ class MessageOverlayController extends State<MessageSelectionOverlay>
 
   double maxWidth = AppConfig.toolbarMinWidth;
 
-  List<PangeaToken> newTokens = [];
-
   /////////////////////////////////////
   /// Lifecycle
   /////////////////////////////////////
@@ -148,14 +147,6 @@ class MessageOverlayController extends State<MessageSelectionOverlay>
           MatrixState.pangeaController.languageController.userL2!.langCode,
         );
       }
-
-      newTokens = pangeaMessageEvent?.messageDisplayRepresentation?.tokens
-              ?.where((token) {
-            return token.lemma.saveVocab == true &&
-                token.vocabConstruct.uses.isEmpty &&
-                messageInUserL2;
-          }).toList() ??
-          [];
     } catch (e, s) {
       debugger(when: kDebugMode);
       ErrorHandler.logError(
@@ -554,14 +545,8 @@ class MessageOverlayController extends State<MessageSelectionOverlay>
     );
 
     if (mounted) {
-      setState(() {
-        newTokens.removeWhere(
-          (t) =>
-              t.text.offset == token.text.offset &&
-              t.text.length == token.text.length &&
-              t.lemma.text.equals(token.lemma.text),
-        );
-      });
+      TokensUtil.clearNewTokenCache(event.eventId);
+      setState(() {});
     }
   }
 
@@ -579,14 +564,8 @@ class MessageOverlayController extends State<MessageSelectionOverlay>
     return isSelected;
   }
 
-  bool isNewToken(PangeaToken token) {
-    if (newTokens.isEmpty) return false;
-    return newTokens.any(
-      (t) =>
-          t.text.offset == token.text.offset &&
-          t.text.length == token.text.length,
-    );
-  }
+  bool isNewToken(PangeaToken token) =>
+      TokensUtil.isNewToken(token, pangeaMessageEvent!);
 
   bool isTokenHighlighted(PangeaToken token) {
     if (_highlightedTokens == null) return false;
diff --git a/lib/pangea/toolbar/widgets/stt_transcript_tokens.dart b/lib/pangea/toolbar/widgets/stt_transcript_tokens.dart
index e63bcb7df..03247a35f 100644
--- a/lib/pangea/toolbar/widgets/stt_transcript_tokens.dart
+++ b/lib/pangea/toolbar/widgets/stt_transcript_tokens.dart
@@ -1,7 +1,7 @@
 import 'package:flutter/material.dart';
 
 import 'package:fluffychat/pangea/events/models/pangea_token_model.dart';
-import 'package:fluffychat/pangea/message_token_text/token_position_model.dart';
+import 'package:fluffychat/pangea/message_token_text/tokens_util.dart';
 import 'package:fluffychat/pangea/toolbar/models/speech_to_text_models.dart';
 
 class SttTranscriptTokens extends StatelessWidget {