diff --git a/lib/pangea/events/utils/message_text_util.dart b/lib/pangea/events/utils/message_text_util.dart
index f23fc30f28..7c829dba3c 100644
--- a/lib/pangea/events/utils/message_text_util.dart
+++ b/lib/pangea/events/utils/message_text_util.dart
@@ -28,7 +28,7 @@ class MessageTextUtil {
       final tokens = pangeaMessageEvent.messageDisplayRepresentation!.tokens!;
       int pointer = 0;
       while (pointer < tokens.length) {
-        final token = tokens[pointer];
+        PangeaToken token = tokens[pointer];
         final start = token.start;
         final end = token.end;
 
@@ -56,13 +56,23 @@ class MessageTextUtil {
           );
         }
 
-        // group tokens with punctuation next to it so punctuation doesn't cause newline
-        final List<PangeaToken> followingPunctTokens = [];
+        // group tokens with punctuation before and after so punctuation doesn't cause newline
         int nextTokenPointer = pointer + 1;
         while (nextTokenPointer < tokens.length) {
           final nextToken = tokens[nextTokenPointer];
-          if (nextToken.pos == 'PUNCT') {
-            followingPunctTokens.add(nextToken);
+          if (token.pos == 'PUNCT' && token.end == nextToken.start) {
+            token = nextToken;
+            nextTokenPointer++;
+            endIndex = messageCharacters.take(nextToken.end).length;
+            continue;
+          }
+          break;
+        }
+
+        while (nextTokenPointer < tokens.length) {
+          final nextToken = tokens[nextTokenPointer];
+
+          if (nextToken.pos == 'PUNCT' && token.end == nextToken.start) {
             nextTokenPointer++;
             endIndex = messageCharacters.take(nextToken.end).length;
             continue;
@@ -74,8 +84,8 @@ class MessageTextUtil {
           TokenPosition(
             start: startIndex,
             end: endIndex,
-            tokenStart: startIndex,
-            tokenEnd: messageCharacters.take(end).length,
+            tokenStart: messageCharacters.take(token.start).length,
+            tokenEnd: messageCharacters.take(token.end).length,
             token: token,
             hideContent: hideContent,
             selected: (isSelected?.call(token) ?? false) &&
diff --git a/lib/pangea/toolbar/widgets/message_token_text.dart b/lib/pangea/toolbar/widgets/message_token_text.dart
index 61d547dc85..82994bdbd8 100644
--- a/lib/pangea/toolbar/widgets/message_token_text.dart
+++ b/lib/pangea/toolbar/widgets/message_token_text.dart
@@ -238,16 +238,24 @@ class MessageTextWidget extends StatelessWidget {
               );
             }
 
-            // if the tokenPosition is a combination of the token and following punctuation
+            // if the tokenPosition is a combination of the token and preceding / following punctuation
             // split them so that only the token itself is highlighted when clicked
-            String firstSubstring = substring;
-            String secondSubstring = '';
+            String start = '';
+            String middle = substring;
+            String end = '';
+
+            if (tokenPosition.tokenStart != tokenPosition.start) {
+              final splitIndex =
+                  (tokenPosition.tokenStart - tokenPosition.start);
+              start = substring.substring(0, splitIndex);
+              middle = substring.substring(splitIndex);
+            }
 
             if (tokenPosition.end != tokenPosition.tokenEnd) {
               final splitIndex = (tokenPosition.end - tokenPosition.start) -
                   (tokenPosition.end - tokenPosition.tokenEnd);
-              firstSubstring = substring.substring(0, splitIndex);
-              secondSubstring = substring.substring(splitIndex);
+              middle = middle.substring(0, splitIndex);
+              end = substring.substring(splitIndex);
             }
 
             return WidgetSpan(
@@ -260,8 +268,22 @@ class MessageTextWidget extends StatelessWidget {
                   child: RichText(
                     text: TextSpan(
                       children: [
+                        if (start.isNotEmpty)
+                          LinkifySpan(
+                            text: start,
+                            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(),
+                          ),
                         LinkifySpan(
-                          text: firstSubstring,
+                          text: middle,
                           style: style.merge(
                             TextStyle(
                               backgroundColor: backgroundColor,
@@ -277,9 +299,9 @@ class MessageTextWidget extends StatelessWidget {
                           onOpen: (url) =>
                               UrlLauncher(context, url.url).launchUrl(),
                         ),
-                        if (secondSubstring.isNotEmpty)
+                        if (end.isNotEmpty)
                           LinkifySpan(
-                            text: secondSubstring,
+                            text: end,
                             style: style,
                             linkStyle: TextStyle(
                               decoration: TextDecoration.underline,