diff --git a/client-web/index.html b/client-web/index.html
index 0d36af5..113f6e5 100644
--- a/client-web/index.html
+++ b/client-web/index.html
@@ -110,7 +110,7 @@
                         </button>
                     </div>
                     <div class="message-input-wrapper">
-                        <input type="text" id="messageInput" placeholder="Send a message..." autofocus>
+                        <textarea style="font-family: sans-serif" id="messageInput" placeholder="Send a message..." autofocus></textarea>
                         <button class="send-button" onclick="sendMessage()">
                             <i class="fa-solid fa-paper-plane"></i>
                         </button>
diff --git a/client-web/index.js b/client-web/index.js
index b7f7602..0c2de7a 100644
--- a/client-web/index.js
+++ b/client-web/index.js
@@ -24,10 +24,17 @@ document.addEventListener('DOMContentLoaded', function() {
             chatHeader.insertBefore(menuToggle, chatHeader.firstChild);
         }
     }
+
+    document.getElementById('messageInput').addEventListener('input', function () {
+        this.style.height = 'auto';
+        this.style.height = (this.scrollHeight) + 'px';
+    });
+
     
     // Add event listeners
-    document.getElementById('messageInput').addEventListener('keypress', (event) => {
-        if (event.key === 'Enter') {
+    document.getElementById('messageInput').addEventListener('keydown', function(event) {
+        if (event.key === 'Enter' && !event.shiftKey) {
+            event.preventDefault();
             sendMessage();
         }
     });
@@ -264,6 +271,218 @@ function resetLoginButton() {
     }
 }
 
+function markdownToHtmlDiv(markdown) {
+  // Emoji mapping
+  const emojiMap = {
+      // 😀 Faces
+      smile: '😄',
+      happy: '😊',
+      grin: '😁',
+      laugh: '😂',
+      joy: '🤣',
+      wink: '😉',
+      blush: '☺️',
+      cool: '😎',
+      smirk: '😏',
+      thinking: '🤔',
+      neutral: '😐',
+      expressionless: '😑',
+      sleepy: '😴',
+      dizzy: '😵',
+      surprised: '😲',
+      scream: '😱',
+      cry: '😢',
+      sob: '😭',
+      angry: '😠',
+      rage: '😡',
+      yum: '😋',
+      relieved: '😌',
+      confused: '😕',
+      nerd: '🤓',
+      zany: '🤪',
+      shush: '🤫',
+      hush: '🤐',
+
+      // ❤️ Emotions
+      heart: '❤️',
+      heartbroken: '💔',
+      love: '😍',
+      kiss: '😘',
+      hug: '🤗',
+      clap: '👏',
+      pray: '🙏',
+      ok: '👌',
+      fingerscrossed: '🤞',
+      thumbsup: '👍',
+      thumbsdown: '👎',
+      eyes: '👀',
+
+      // 🔥 Reactions
+      fire: '🔥',
+      100: '💯',
+      poop: '💩',
+      poo: '💩',
+      skull: '💀',
+      explosion: '💥',
+      mindblown: '🤯',
+      party: '🥳',
+      tada: '🎉',
+      balloon: '🎈',
+
+      // 🐶 Animals
+      chicken: '🐔',
+      dog: '🐶',
+      cat: '🐱',
+      fox: '🦊',
+      panda: '🐼',
+      pig: '🐷',
+      cow: '🐮',
+      rabbit: '🐰',
+      bear: '🐻',
+      unicorn: '🦄',
+      monkey: '🐒',
+      dragon: '🐉',
+      snake: '🐍',
+
+      // 🍔 Food & Drink
+      pizza: '🍕',
+      burger: '🍔',
+      fries: '🍟',
+      hotdog: '🌭',
+      taco: '🌮',
+      ramen: '🍜',
+      sushi: '🍣',
+      icecream: '🍨',
+      cake: '🎂',
+      coffee: '☕',
+      tea: '🍵',
+      beer: '🍺',
+
+      // 🌍 Nature & Weather
+      sun: '☀️',
+      moon: '🌙',
+      star: '⭐',
+      cloud: '☁️',
+      rain: '🌧️',
+      snow: '❄️',
+      lightning: '⚡',
+      rainbow: '🌈',
+      tree: '🌳',
+      flower: '🌸',
+
+      // ⚽ Activities
+      soccer: '⚽',
+      basketball: '🏀',
+      football: '🏈',
+      baseball: '⚾',
+      tennis: '🎾',
+      bowling: '🎳',
+      video_game: '🎮',
+      chess: '♟️',
+      music: '🎵',
+      guitar: '🎸',
+      mic: '🎤',
+
+      // 💡 Objects & Symbols
+      lightbulb: '💡',
+      phone: '📱',
+      laptop: '💻',
+      bomb: '💣',
+      money: '💰',
+      star2: '🌟',
+      warning: '⚠️',
+      check: '✅',
+      x: '❌',
+      question: '❓',
+      exclamation: '❗',
+      infinity: '♾️',
+      hourglass: '⏳',
+      clock: '🕒',
+
+      pepe: '🐸',
+      troll: '😈',
+      sus: '🧐',
+      amongus: '🟥',
+      monke: '🐵',
+      chad: '🦍',
+      gigachad: '💪',
+      wojak: '😔',
+      feelsbadman: '😞',
+      feelsgoodman: '😌',
+      yikes: '😬',
+      clown: '🤡',
+      clownworld: '🌎🤡',
+      triggered: '😡',
+      pog: '😲',
+      kek: '🤣',
+      based: '😎',
+      cringe: '😖',
+      dab: '🕺',
+      sigma: '🧠',
+      npc: '🤖',
+      doomer: '🌑',
+      zoomer: '⚡',
+      boomer: '👴',
+      sheesh: '😤',
+      rickroll: '🕺🎶',
+      trolled: '🧌',
+      rekt: '💀',
+      skillissue: '📉',
+      bro: '🙄',
+      cope: '😢',
+      ratio: '➗',
+      amogus: '👁️👄👁️',
+
+};
+
+  // Escape HTML first
+  let html = markdown
+    .replace(/&/g, '&amp;')
+    .replace(/</g, '&lt;')
+    .replace(/>/g, '&gt;');
+
+  // Code blocks (```...```)
+  html = html.replace(/```([^```]*)```/gs, (match, p1) =>
+    `<pre><code>${p1.trim()}</code></pre>`
+  );
+
+  // Inline code (`code`)
+  html = html.replace(/`([^`\n]+)`/g, (match, p1) => `<code>${p1}</code>`);
+
+  // Emojis :emoji_name:
+  html = html.replace(/:([a-z0-9_]+):/gi, (match, p1) => emojiMap[p1] || match);
+
+  // Process overlapping formatting in order: Bold+Underline+Italic
+  html = parseFormatting(html);
+
+  // Replace line breaks
+  html = html.replace(/\n/g, '<br>');
+
+  return html;
+}
+
+// Parse overlapping formatting using tokens
+function parseFormatting(text) {
+  // Define replacement tokens and their HTML
+  const formattingRules = [
+    { regex: /\*\*\*(.*?)\*\*\*/g, html: '<strong><em>$1</em></strong>' }, // ***bold italic***
+    { regex: /___(.*?)___/g, html: '<u><em>$1</em></u>' },                 // ___underline italic___
+    { regex: /\*\*(.*?)\*\*/g, html: '<strong>$1</strong>' },             // **bold**
+    { regex: /__(.*?)__/g, html: '<u>$1</u>' },                           // __underline__
+    { regex: /\*(.*?)\*/g, html: '<em>$1</em>' },                         // *italic*
+    { regex: /_(.*?)_/g, html: '<em>$1</em>' },                           // _italic_
+    { regex: /~~(.*?)~~/g, html: '<s>$1</s>' }                            // ~~strike~~
+  ];
+
+  // Apply formatting in order
+  for (const rule of formattingRules) {
+    text = text.replace(rule.regex, rule.html);
+  }
+
+  return text;
+}
+
+
 // Handle incoming messages
 function handleMessage(event) {
     if (event.data === "ping") {
@@ -618,7 +837,7 @@ function addChatMessage(author, content, isHistory = false) {
     // Add message text
     const textDiv = document.createElement('div');
     textDiv.className = 'message-text';
-    textDiv.textContent = content;
+    textDiv.innerHTML = markdownToHtmlDiv(content);
     contentDiv.appendChild(textDiv);
     
     messageWrapper.appendChild(avatar);
@@ -797,6 +1016,8 @@ async function uploadFile() {
     const formData = new FormData();
     formData.append("file", fileInput.files[0]);
     formData.append("room", currentRoom); 
+    formData.append("username", username);
+    formData.append("token", md5(password));
     
     try {
         const response = await fetch(getUploadUrl(), {
@@ -807,17 +1028,6 @@ async function uploadFile() {
         
         if (response.ok) {
             hideFileUpload();
-            
-            const processedMessage = {
-                "type": "message",
-                "username": username,
-                "token": md5(password),
-                "room": currentRoom,
-                "content": `Sent a file`
-            }
-            if (ws && ws.readyState === WebSocket.OPEN) {
-                ws.send(JSON.stringify(processedMessage));
-            }
         } else {
             alert("Failed to upload file. Please try again.");
         }
@@ -1143,4 +1353,4 @@ if (uploadField) {
             this.value = "";
         }
     };
-}
\ No newline at end of file
+}
diff --git a/server/src/main/kotlin/Main.kt b/server/src/main/kotlin/Main.kt
index 70e7d7c..47c05da 100644
--- a/server/src/main/kotlin/Main.kt
+++ b/server/src/main/kotlin/Main.kt
@@ -798,6 +798,20 @@ fun main(args: Array<String>) {
             Files.copy(uploadedFile.content(), filePath)
             
             val room = if (ctx.formParam("room") != null) ctx.formParam("room") else "general"
+            var username: String = ""
+            var token: String = ""
+
+            if (ctx.formParam("username") != null) {
+                username = ctx.formParam("username").toString()
+            } else {
+                // do error
+            }
+
+            if (ctx.formParam("token") != null) {
+                token = ctx.formParam("token").toString()
+            } else {
+                // do error
+            }
             
             val processedData = JSONObject().apply {
                 put("type", "fileStatus")
@@ -808,7 +822,7 @@ fun main(args: Array<String>) {
             
             val processedData2 = JSONObject().apply {
                 put("type", "file")
-                put("username", "system")
+                put("username", username)
                 put("room", room)
                 put("content", "https://maxwellj.xyz/chookchat/uploads/$newFilename")
             }