diff --git a/lib/pangea/events/utils/message_text_util.dart b/lib/pangea/events/utils/message_text_util.dart
index 825c19fc3..f23fc30f2 100644
--- a/lib/pangea/events/utils/message_text_util.dart
+++ b/lib/pangea/events/utils/message_text_util.dart
@@ -25,14 +25,16 @@ class MessageTextUtil {
       final List<TokenPosition> tokenPositions = [];
       int globalIndex = 0;
 
-      for (final token
-          in pangeaMessageEvent.messageDisplayRepresentation!.tokens!) {
+      final tokens = pangeaMessageEvent.messageDisplayRepresentation!.tokens!;
+      int pointer = 0;
+      while (pointer < tokens.length) {
+        final token = tokens[pointer];
         final start = token.start;
         final end = token.end;
 
         // Calculate the number of grapheme clusters up to the start and end positions
         final int startIndex = messageCharacters.take(start).length;
-        final int endIndex = messageCharacters.take(end).length;
+        int endIndex = messageCharacters.take(end).length;
 
         final hideContent =
             messageAnalyticsEntry?.isTokenInHiddenWordActivity(token) ?? false;
@@ -40,21 +42,40 @@ class MessageTextUtil {
         final hasHiddenContent =
             messageAnalyticsEntry?.hasHiddenWordActivity ?? false;
 
+        // if this is white space, add position without token
         if (globalIndex < startIndex) {
           tokenPositions.add(
             TokenPosition(
               start: globalIndex,
               end: startIndex,
+              tokenStart: globalIndex,
+              tokenEnd: startIndex,
               hideContent: false,
               selected: (isSelected?.call(token) ?? false) && !hasHiddenContent,
             ),
           );
         }
 
+        // group tokens with punctuation next to it so punctuation doesn't cause newline
+        final List<PangeaToken> followingPunctTokens = [];
+        int nextTokenPointer = pointer + 1;
+        while (nextTokenPointer < tokens.length) {
+          final nextToken = tokens[nextTokenPointer];
+          if (nextToken.pos == 'PUNCT') {
+            followingPunctTokens.add(nextToken);
+            nextTokenPointer++;
+            endIndex = messageCharacters.take(nextToken.end).length;
+            continue;
+          }
+          break;
+        }
+
         tokenPositions.add(
           TokenPosition(
             start: startIndex,
             end: endIndex,
+            tokenStart: startIndex,
+            tokenEnd: messageCharacters.take(end).length,
             token: token,
             hideContent: hideContent,
             selected: (isSelected?.call(token) ?? false) &&
@@ -62,7 +83,10 @@ class MessageTextUtil {
                 !hasHiddenContent,
           ),
         );
+
         globalIndex = endIndex;
+        pointer = nextTokenPointer;
+        continue;
       }
 
       return tokenPositions;
diff --git a/lib/pangea/toolbar/widgets/message_token_text.dart b/lib/pangea/toolbar/widgets/message_token_text.dart
index 233f87b33..61d547dc8 100644
--- a/lib/pangea/toolbar/widgets/message_token_text.dart
+++ b/lib/pangea/toolbar/widgets/message_token_text.dart
@@ -70,8 +70,18 @@ class MessageTokenText extends StatelessWidget {
 }
 
 class TokenPosition {
+  /// Start index of the full substring in the message
   final int start;
+
+  /// End index of the full substring in the message
   final int end;
+
+  /// Start index of the token in the message
+  final int tokenStart;
+
+  /// End index of the token in the message
+  final int tokenEnd;
+
   final bool selected;
   final bool hideContent;
   final PangeaToken? token;
@@ -79,6 +89,8 @@ class TokenPosition {
   const TokenPosition({
     required this.start,
     required this.end,
+    required this.tokenStart,
+    required this.tokenEnd,
     required this.hideContent,
     required this.selected,
     this.token,
@@ -225,6 +237,19 @@ class MessageTextWidget extends StatelessWidget {
                 ),
               );
             }
+
+            // if the tokenPosition is a combination of the token and following punctuation
+            // split them so that only the token itself is highlighted when clicked
+            String firstSubstring = substring;
+            String secondSubstring = '';
+
+            if (tokenPosition.end != tokenPosition.tokenEnd) {
+              final splitIndex = (tokenPosition.end - tokenPosition.start) -
+                  (tokenPosition.end - tokenPosition.tokenEnd);
+              firstSubstring = substring.substring(0, splitIndex);
+              secondSubstring = substring.substring(splitIndex);
+            }
+
             return WidgetSpan(
               child: MouseRegion(
                 cursor: SystemMouseCursors.click,
@@ -233,21 +258,40 @@ class MessageTextWidget extends StatelessWidget {
                       ? () => onClick?.call(tokenPosition)
                       : null,
                   child: RichText(
-                    text: LinkifySpan(
-                      text: substring,
-                      style: style.merge(
-                        TextStyle(
-                          backgroundColor: backgroundColor,
+                    text: TextSpan(
+                      children: [
+                        LinkifySpan(
+                          text: firstSubstring,
+                          style: style.merge(
+                            TextStyle(
+                              backgroundColor: backgroundColor,
+                            ),
+                          ),
+                          linkStyle: TextStyle(
+                            decoration: TextDecoration.underline,
+                            color:
+                                Theme.of(context).brightness == Brightness.light
+                                    ? Theme.of(context).colorScheme.primary
+                                    : Theme.of(context).colorScheme.onPrimary,
+                          ),
+                          onOpen: (url) =>
+                              UrlLauncher(context, url.url).launchUrl(),
                         ),
-                      ),
-                      linkStyle: TextStyle(
-                        decoration: TextDecoration.underline,
-                        color: Theme.of(context).brightness == Brightness.light
-                            ? Theme.of(context).colorScheme.primary
-                            : Theme.of(context).colorScheme.onPrimary,
-                      ),
-                      onOpen: (url) =>
-                          UrlLauncher(context, url.url).launchUrl(),
+                        if (secondSubstring.isNotEmpty)
+                          LinkifySpan(
+                            text: secondSubstring,
+                            style: style,
+                            linkStyle: TextStyle(
+                              decoration: TextDecoration.underline,
+                              color: Theme.of(context).brightness ==
+                                      Brightness.light
+                                  ? Theme.of(context).colorScheme.primary
+                                  : Theme.of(context).colorScheme.onPrimary,
+                            ),
+                            onOpen: (url) =>
+                                UrlLauncher(context, url.url).launchUrl(),
+                          ),
+                      ],
                     ),
                   ),
                 ),