diff --git a/ChatTwo/Chunk.cs b/ChatTwo/Chunk.cs
index f30b248..7b44562 100755
--- a/ChatTwo/Chunk.cs
+++ b/ChatTwo/Chunk.cs
@@ -70,6 +70,11 @@ public class TextChunk : Chunk
     [Key(6)]
     public string Content { get; set; }
 
+    private TextChunk(Chunk chunk, string content) : base(chunk.Source, chunk.Link)
+    {
+        Content = content;
+    }
+
     internal TextChunk(ChunkSource source, Payload? link, string content) : base(source, link)
     {
         // This has been null in the past, and it broke rendering code.
@@ -102,6 +107,20 @@ public class TextChunk : Chunk
             Italic = Italic,
         };
     }
+
+    /// <summary>
+    /// Creates a new TextChunk with identical styling to this one.
+    /// </summary>
+    public TextChunk NewWithStyle(Chunk chunk, string content)
+    {
+        return new TextChunk(chunk, content)
+        {
+            FallbackColour = FallbackColour,
+            Foreground = Foreground,
+            Glow = Glow,
+            Italic = Italic,
+        };
+    }
 }
 
 [MessagePackObject]
diff --git a/ChatTwo/Message.cs b/ChatTwo/Message.cs
index 155e116..42209c6 100755
--- a/ChatTwo/Message.cs
+++ b/ChatTwo/Message.cs
@@ -153,47 +153,10 @@ internal partial class Message
             newChunks.Add(chunk);
         }
 
-        void AddContentAfterURLCheck(string content, TextChunk text, Chunk chunk)
-        {
-            // This works because c# will split regex string, while keeping named groups as separated splits
-            // If the match is the first content of a string, the array will start with a ""
-            // Same if 2 matches are next to each other, they will be split with a ""
-            var splits = URLRegex.Split(content);
-            if (splits.Length == 1)
-            {
-                AddChunkWithMessage(text.NewWithStyle(chunk.Source, chunk.Link, content));
-                return;
-            }
-
-            var nextIsMatch = false;
-            foreach (var split in splits)
-            {
-                if (split == "" || !nextIsMatch)
-                {
-                    nextIsMatch = true;
-                    AddChunkWithMessage(text.NewWithStyle(chunk.Source, chunk.Link, split));
-                    continue;
-                }
-
-                // Create a new TextChunk with a URIPayload for the URL text.
-                nextIsMatch = false;
-                try
-                {
-                    var link = UriPayload.ResolveURI(split);
-                    AddChunkWithMessage(text.NewWithStyle(chunk.Source, link, split));
-                }
-                catch (UriFormatException)
-                {
-                    AddChunkWithMessage(text.NewWithStyle(chunk.Source, chunk.Link, split));
-                    Plugin.Log.Debug($"Invalid URL accepted by Regex but failed URI parsing: '{split}'");
-                }
-            }
-        }
-
         var checkForEmotes = (Code.IsPlayerMessage() || extraChatChannel != Guid.Empty) && Plugin.Config.ShowEmotes;
         foreach (var chunk in oldChunks)
         {
-            // Use as is if it's not a text chunk or it already has a payload.
+            // Use as is if it's not a text chunk, or it already has a payload.
             if (chunk is not TextChunk text || chunk.Link != null)
             {
                 // No need to call AddChunkWithMessage here since the chunk
@@ -215,28 +178,49 @@ internal partial class Message
                 var word = wordBuilder.ToString();
                 wordBuilder.Clear();
 
+
+                var wordUsed = false;
+                var tokenUsed = false;
+
                 if (checkForEmotes && EmoteCache.Exists(word) && !Plugin.Config.BlockedEmotes.Contains(word))
                 {
-                    // Add the previous sentence before the emote
-                    AddContentAfterURLCheck(sentenceBuilder.ToString(), text, chunk);
+                    // Add the previous sentence before adding the emote
+                    AddChunkWithMessage(text.NewWithStyle(chunk, sentenceBuilder.ToString()));
                     AddChunkWithMessage(new TextChunk(chunk.Source, EmotePayload.ResolveEmote(word), word) { FallbackColour = text.FallbackColour });
 
-                    // Append the current punctuation symbol
+                    wordUsed = true;
+                    sentenceBuilder.Clear();
+                }
+
+                if (token.TokenType == Tokenizer.TokenType.UrlString)
+                {
+                    // Add the previous sentence before adding the url
+                    AddChunkWithMessage(text.NewWithStyle(chunk.Source, chunk.Link, sentenceBuilder.Append(!wordUsed ? word : "").ToString()));
+                    try
+                    {
+                        AddChunkWithMessage(text.NewWithStyle(chunk.Source, UriPayload.ResolveURI(token.Value), token.Value));
+                    }
+                    catch (UriFormatException)
+                    {
+                        AddChunkWithMessage(text.NewWithStyle(chunk.Source, chunk.Link, token.Value));
+                        Plugin.Log.Debug($"Invalid URL accepted by Regex but failed URI parsing: '{token.Value}'");
+                    }
+
+                    wordUsed = true;
+                    tokenUsed = true;
                     sentenceBuilder.Clear();
-                    sentenceBuilder.Append(token.Value);
-                    continue;
                 }
 
                 // Append match if we haven't reached end of string yet
                 if (token.TokenType != Tokenizer.TokenType.SequenceTerminator)
                 {
-                    sentenceBuilder.Append(word);
-                    sentenceBuilder.Append(token.Value);
+                    sentenceBuilder.Append(!wordUsed ? word : "");
+                    sentenceBuilder.Append(!tokenUsed ? token.Value : "");
                     continue;
                 }
 
                 // End of string reached, we add our leftover
-                AddContentAfterURLCheck(sentenceBuilder.Append(word).ToString(), text, chunk);
+                AddChunkWithMessage(text.NewWithStyle(chunk, sentenceBuilder.Append(!wordUsed ? word : "").ToString()));
             }
         }
 
@@ -340,23 +324,6 @@ internal partial class Message
         Content = newChunks;
     }
 
-    /// <summary>
-    /// URLRegex returns a regex object that matches URLs like:
-    /// - https://example.com
-    /// - http://example.com
-    /// - www.example.com
-    /// - https://sub.example.com
-    /// - example.com
-    /// - sub.example.com
-    ///
-    /// It matches URLs with www. or https:// prefix, and also matches URLs
-    /// without a prefix on specific TLDs.
-    /// </summary>
-    private static Regex URLRegex = new(
-        @"(?<URL>((https?:\/\/|www\.)[a-z0-9-]+(\.[a-z0-9-]+)*|([a-z0-9-]+(\.[a-z0-9-]+)*\.(com|net|org|co|io|app)))(:[\d]{1,5})?(\/[^\s]+)?)",
-        RegexOptions.Compiled | RegexOptions.IgnoreCase | RegexOptions.ExplicitCapture
-    );
-
     [GeneratedRegex("(<item>|<flag>)")]
     private static partial Regex TextParamRegex();
 }
diff --git a/ChatTwo/Resources/Language.Designer.cs b/ChatTwo/Resources/Language.Designer.cs
index 48a01d2..e668d90 100755
--- a/ChatTwo/Resources/Language.Designer.cs
+++ b/ChatTwo/Resources/Language.Designer.cs
@@ -2409,7 +2409,7 @@ namespace ChatTwo.Resources {
         }
         
         /// <summary>
-        ///   Looks up a localized string similar to Text Preview:.
+        ///   Looks up a localized string similar to Message Preview:.
         /// </summary>
         internal static string Options_Preview_Header {
             get {
@@ -2427,7 +2427,7 @@ namespace ChatTwo.Resources {
         }
         
         /// <summary>
-        ///   Looks up a localized string similar to Text preview.
+        ///   Looks up a localized string similar to Message preview.
         /// </summary>
         internal static string Options_Preview_Name {
             get {
diff --git a/ChatTwo/Resources/Language.resx b/ChatTwo/Resources/Language.resx
index d91b1cf..2f450a8 100644
--- a/ChatTwo/Resources/Language.resx
+++ b/ChatTwo/Resources/Language.resx
@@ -1055,7 +1055,7 @@
         <value>Displays a preview with special parameter evaluated, like emotes and &lt;item&gt;</value>
     </data>
     <data name="Options_Preview_Name" xml:space="preserve">
-        <value>Text preview</value>
+        <value>Message preview</value>
     </data>
     <data name="Options_Preview_None" xml:space="preserve">
         <value>None</value>
@@ -1070,7 +1070,7 @@
         <value>Bottom</value>
     </data>
     <data name="Options_Preview_Header" xml:space="preserve">
-        <value>Text Preview:</value>
+        <value>Message Preview:</value>
     </data>
     <data name="Options_Preview_Tooltip" xml:space="preserve">
         <value>Tooltip</value>
diff --git a/ChatTwo/Ui/ChatLogWindow.cs b/ChatTwo/Ui/ChatLogWindow.cs
index 7886d75..3d00dc2 100644
--- a/ChatTwo/Ui/ChatLogWindow.cs
+++ b/ChatTwo/Ui/ChatLogWindow.cs
@@ -49,7 +49,7 @@ public sealed class ChatLogWindow : Window
         }
     }
 
-    internal bool KeepFocusedThroughPreview;
+    internal bool FocusedPreview;
     internal bool Activate;
     private int ActivatePos = -1;
     internal string Chat = string.Empty;
@@ -686,9 +686,9 @@ public sealed class ChatLogWindow : Window
         var push = inputColour != null;
         using (ImRaii.PushColor(ImGuiCol.Text, push ? ColourUtil.RgbaToAbgr(inputColour!.Value) : 0, push))
         {
-            if (Activate || KeepFocusedThroughPreview)
+            if (Activate || FocusedPreview)
             {
-                KeepFocusedThroughPreview = false;
+                FocusedPreview = false;
                 ImGui.SetKeyboardFocusHere();
             }
 
diff --git a/ChatTwo/Ui/InputPreview.cs b/ChatTwo/Ui/InputPreview.cs
index 727707c..de92e1a 100644
--- a/ChatTwo/Ui/InputPreview.cs
+++ b/ChatTwo/Ui/InputPreview.cs
@@ -1,6 +1,7 @@
 using System.Numerics;
 using System.Reflection;
 using System.Text;
+using System.Text.RegularExpressions;
 using ChatTwo.Code;
 using ChatTwo.Resources;
 using ChatTwo.Util;
@@ -14,7 +15,7 @@ using ImGuiNET;
 
 namespace ChatTwo.Ui;
 
-public class InputPreview : Window
+public partial class InputPreview : Window
 {
     private ChatLogWindow LogWindow { get; }
 
@@ -231,24 +232,20 @@ public class InputPreview : Window
                 CursorPosition += "<flag>".Length;
             else if (text.Link is EmotePayload emote)
                 CursorPosition += emote.Code.Length;
+            else if (text.Link is UriPayload)
+                CursorPosition += text.Content.Length;
 
             ImGuiUtil.WrapText(text.Content, chunk, handler, LogWindow.DefaultText, lineWidth);
             return;
         }
 
-        var splits = text.Content.Split(" ");
-        for (var i = 0; i < splits.Length; i++)
+        foreach (var word in WhitespaceRegex().Split(text.Content).Where(s => s != string.Empty))
         {
-            // The last character should never be an empty string
-            // Sorting this out because it leads to double whitespaces
-            if (i + 1 == splits.Length && splits[i] == "")
-                break;
-
-            var wordSize = ImGui.CalcTextSize(splits[i]);
+            var wordSize = ImGui.CalcTextSize(word);
             if (ImGui.GetContentRegionAvail().X < wordSize.X)
                 ImGui.NewLine();
 
-            foreach (var letter in $"{splits[i]} ")
+            foreach (var letter in word)
             {
                 var letterSize = ImGui.CalcTextSize(letter.ToString());
 
@@ -256,11 +253,14 @@ public class InputPreview : Window
                 if (ImGui.Selectable($"{letter}##{CursorPosition + unique}", false, ImGuiSelectableFlags.None, letterSize))
                 {
                     SelectedCursorPos = CursorPosition;
-                    LogWindow.KeepFocusedThroughPreview = true;
+                    LogWindow.FocusedPreview = true;
                 }
                 ImGui.SameLine();
             }
         }
         ImGui.NewLine();
     }
+
+    [GeneratedRegex(@"(\s)")]
+    private static partial Regex WhitespaceRegex();
 }
diff --git a/ChatTwo/Util/Tokenizer.cs b/ChatTwo/Util/Tokenizer.cs
index 0b5ac1c..9092c7e 100644
--- a/ChatTwo/Util/Tokenizer.cs
+++ b/ChatTwo/Util/Tokenizer.cs
@@ -16,6 +16,7 @@ public static class Tokenizer
         Whitespace,
         Equals,
         OpenParenthesis,
+        UrlString,
         StringValue,
         Leftover,
         SequenceTerminator
@@ -46,6 +47,7 @@ public static class Tokenizer
                 new(TokenType.Whitespace, "\\s", 1),
                 new(TokenType.Equals, "=", 1),
                 new(TokenType.OpenParenthesis, "\\(", 1),
+                new(TokenType.UrlString, URLRegex, 1),
                 new(TokenType.StringValue, "\\p{IsBasicLatin}", 2),
                 new(TokenType.Leftover, ".", 3)
             };
@@ -85,9 +87,25 @@ public static class Tokenizer
         }
     }
 
-    private class TokenDefinition(TokenType returnsToken, string regexPattern, int precedence)
+    private class TokenDefinition
     {
-        private readonly Regex Regex = new(regexPattern, RegexOptions.IgnoreCase|RegexOptions.Compiled);
+        private readonly TokenType Type;
+        private readonly int Precedence;
+        private readonly Regex Regex;
+
+        public TokenDefinition(TokenType returnsToken, string regexPattern, int precedence)
+        {
+            Type = returnsToken;
+            Precedence = precedence;
+            Regex = new Regex(regexPattern, RegexOptions.IgnoreCase|RegexOptions.Compiled);
+        }
+
+        public TokenDefinition(TokenType returnsToken, Regex regex, int precedence)
+        {
+            Type = returnsToken;
+            Precedence = precedence;
+            Regex = regex;
+        }
 
         public IEnumerable<TokenMatch> FindMatches(string inputString)
         {
@@ -98,9 +116,9 @@ public static class Tokenizer
                 {
                     StartIndex = matches[i].Index,
                     EndIndex = matches[i].Index + matches[i].Length,
-                    TokenType = returnsToken,
+                    TokenType = Type,
                     Value = matches[i].Value,
-                    Precedence = precedence
+                    Precedence = Precedence
                 };
             }
         }
@@ -114,4 +132,21 @@ public static class Tokenizer
         public int EndIndex { get; set; }
         public int Precedence { get; set; }
     }
+
+    /// <summary>
+    /// URLRegex returns a regex object that matches URLs like:
+    /// - https://example.com
+    /// - http://example.com
+    /// - www.example.com
+    /// - https://sub.example.com
+    /// - example.com
+    /// - sub.example.com
+    ///
+    /// It matches URLs with www. or https:// prefix, and also matches URLs
+    /// without a prefix on specific TLDs.
+    /// </summary>
+    private static Regex URLRegex = new(
+        @"(?<URL>((https?:\/\/|www\.)[a-z0-9-]+(\.[a-z0-9-]+)*|([a-z0-9-]+(\.[a-z0-9-]+)*\.(com|net|org|co|io|app)))(:[\d]{1,5})?(\/[^\s]*)?)",
+        RegexOptions.Compiled | RegexOptions.IgnoreCase | RegexOptions.ExplicitCapture
+    );
 }
\ No newline at end of file