diff --git a/crates/goose-server/Cargo.toml b/crates/goose-server/Cargo.toml
index 3c5c7451..a89ebf98 100644
--- a/crates/goose-server/Cargo.toml
+++ b/crates/goose-server/Cargo.toml
@@ -25,6 +25,9 @@ http-body-util = "0.1"
 http = "1.0"
 config = { version = "0.14.1", features = ["toml"] }
 thiserror = "1.0"
+reqwest = "0.11"
+scraper = "0.12.0"
+url = "2.2.2"
 
 [[bin]]
 name = "goosed"
diff --git a/crates/goose-server/lib.rs b/crates/goose-server/lib.rs
new file mode 100644
index 00000000..9b603f76
--- /dev/null
+++ b/crates/goose-server/lib.rs
@@ -0,0 +1 @@
+use crate::routes::metadata; 
\ No newline at end of file
diff --git a/crates/goose-server/src/routes/metadata.rs b/crates/goose-server/src/routes/metadata.rs
new file mode 100644
index 00000000..2ec96aa4
--- /dev/null
+++ b/crates/goose-server/src/routes/metadata.rs
@@ -0,0 +1,176 @@
+use axum::{
+    extract::Query,
+    response::Json,
+    routing::get,
+    Router,
+};
+use reqwest::header::USER_AGENT;
+use scraper::{Html, Selector};
+use serde::{Deserialize, Serialize};
+use std::collections::HashMap;
+use url::Url;
+use tracing::{info, error, warn};
+
+#[derive(Debug, Serialize)]
+pub struct Metadata {
+    title: Option<String>,
+    description: Option<String>,
+    favicon: Option<String>,
+    image: Option<String>,
+    url: String,
+}
+
+#[derive(Debug, Deserialize)]
+pub struct MetadataQuery {
+    url: String,
+}
+
+pub async fn get_metadata(
+    Query(params): Query<HashMap<String, String>>,
+) -> Json<Metadata> {
+    let url = params.get("url").expect("URL is required");
+    info!("📨 Received metadata request for URL: {}", url);
+
+    let metadata = fetch_metadata(url).await.unwrap_or_else(|e| {
+        error!("❌ Error fetching metadata: {:?}", e);
+        Metadata {
+            title: None,
+            description: None,
+            favicon: None,
+            image: None,
+            url: url.to_string(),
+        }
+    });
+
+    info!("✅ Returning metadata: {:?}", metadata);
+    Json(metadata)
+}
+
+async fn fetch_metadata(url: &str) -> Result<Metadata, Box<dyn std::error::Error>> {
+    info!("🌐 Making request to: {}", url);
+    
+    let client = reqwest::Client::new();
+    let response = client
+        .get(url)
+        .header(USER_AGENT, "Mozilla/5.0 (compatible; Goose/1.0)")
+        .send()
+        .await?;
+
+    info!("📥 Response status: {}", response.status());
+    info!("📤 Response headers: {:?}", response.headers());
+
+    let html = response.text().await?;
+    let document = Html::parse_document(&html);
+    let base_url = Url::parse(url)?;
+
+    info!("📄 Successfully parsed HTML document");
+
+    // Title selector with detailed logging
+    let title = document
+        .select(&Selector::parse("title").unwrap())
+        .next()
+        .map(|el| el.text().collect::<String>())
+        .or_else(|| {
+            info!("⚠️ No <title> tag found, trying OpenGraph title");
+            document
+                .select(&Selector::parse("meta[property='og:title']").unwrap())
+                .next()
+                .and_then(|el| el.value().attr("content"))
+                .map(String::from)
+        });
+
+    info!("📝 Found title: {:?}", title);
+
+    // Description selector with fallbacks
+    let description = document
+        .select(&Selector::parse("meta[name='description']").unwrap())
+        .next()
+        .or_else(|| {
+            info!("⚠️ No meta description found, trying OpenGraph description");
+            document
+                .select(&Selector::parse("meta[property='og:description']").unwrap())
+                .next()
+        })
+        .and_then(|el| el.value().attr("content"))
+        .map(String::from);
+
+    info!("📝 Found description: {:?}", description);
+
+    // Favicon with detailed error logging
+    let favicon = match find_favicon(&document, &base_url) {
+        Ok(Some(url)) => {
+            info!("🎨 Found favicon: {}", url);
+            Some(url)
+        }
+        Ok(None) => {
+            warn!("⚠️ No favicon found");
+            None
+        }
+        Err(e) => {
+            error!("❌ Error finding favicon: {:?}", e);
+            None
+        }
+    };
+
+    // OpenGraph image with logging
+    let image = document
+        .select(&Selector::parse("meta[property='og:image']").unwrap())
+        .next()
+        .and_then(|el| el.value().attr("content"))
+        .map(|src| {
+            info!("🖼️ Found OpenGraph image: {}", src);
+            resolve_url(&base_url, src)
+        })
+        .transpose()?;
+
+    let metadata = Metadata {
+        title,
+        description,
+        favicon,
+        image,
+        url: url.to_string(),
+    };
+
+    info!("✨ Successfully built metadata: {:?}", metadata);
+    Ok(metadata)
+}
+
+fn find_favicon(document: &Html, base_url: &Url) -> Result<Option<String>, Box<dyn std::error::Error>> {
+    info!("🔍 Searching for favicon");
+    
+    let favicon_selectors = [
+        "link[rel='icon']",
+        "link[rel='shortcut icon']",
+        "link[rel='apple-touch-icon']",
+        "link[rel='apple-touch-icon-precomposed']",
+    ];
+
+    for selector in favicon_selectors {
+        info!("👀 Trying selector: {}", selector);
+        if let Some(favicon) = document
+            .select(&Selector::parse(selector).unwrap())
+            .next()
+            .and_then(|el| el.value().attr("href"))
+        {
+            info!("✅ Found favicon with selector {}: {}", selector, favicon);
+            if let Ok(absolute_url) = resolve_url(base_url, favicon) {
+                return Ok(Some(absolute_url));
+            }
+        }
+    }
+
+    info!("ℹ️ Using fallback favicon.ico");
+    Ok(Some(base_url.join("/favicon.ico")?.to_string()))
+}
+
+fn resolve_url(base: &Url, path: &str) -> Result<String, Box<dyn std::error::Error>> {
+    info!("🔗 Resolving URL - Base: {}, Path: {}", base, path);
+    let resolved = base.join(path)?.to_string();
+    info!("✅ Resolved URL: {}", resolved);
+    Ok(resolved)
+}
+
+pub fn routes() -> Router {
+    Router::new()
+        .route("/api/metadata", get(get_metadata))
+}
\ No newline at end of file
diff --git a/crates/goose-server/src/routes/mod.rs b/crates/goose-server/src/routes/mod.rs
index 2d798a0d..6b3d7cdb 100644
--- a/crates/goose-server/src/routes/mod.rs
+++ b/crates/goose-server/src/routes/mod.rs
@@ -1,9 +1,12 @@
 // Export route modules
 pub mod reply;
+pub mod metadata; 
 
 use axum::Router;
+use crate::state::AppState;
 
 // Function to configure all routes
-pub fn configure(state: crate::state::AppState) -> Router {
+pub fn configure(state: AppState) -> Router {
     Router::new().merge(reply::routes(state))
+        .merge(metadata::routes())
 }
diff --git a/ui/desktop/package-lock.json b/ui/desktop/package-lock.json
index 4ef278df..ae91d044 100644
--- a/ui/desktop/package-lock.json
+++ b/ui/desktop/package-lock.json
@@ -27,6 +27,7 @@
         "electron-squirrel-startup": "^1.0.1",
         "express": "^4.21.1",
         "framer-motion": "^11.11.11",
+        "linkifyjs": "^4.1.4",
         "lucide-react": "^0.454.0",
         "react": "^18.3.1",
         "react-dom": "^18.3.1",
@@ -7242,6 +7243,11 @@
       "resolved": "https://artifactory.global.square/artifactory/api/npm/square-npm/lines-and-columns/-/lines-and-columns-1.2.4.tgz",
       "integrity": "sha512-7ylylesZQ/PV29jhEDl3Ufjo6ZX7gCqJr5F7PKrqc93v7fzSymt1BpwEU8nAUXs8qzzvqhbjhK5QZg6Mt/HkBg=="
     },
+    "node_modules/linkifyjs": {
+      "version": "4.1.4",
+      "resolved": "https://artifactory.global.square/artifactory/api/npm/square-npm/linkifyjs/-/linkifyjs-4.1.4.tgz",
+      "integrity": "sha512-0/NxkHNpiJ0k9VrYCkAn9OtU1eu8xEr1tCCpDtSsVRm/SF0xAak2Gzv3QimSfgUgqLBCDlfhMbu73XvaEHUTPQ=="
+    },
     "node_modules/listr2": {
       "version": "7.0.2",
       "resolved": "https://artifactory.global.square/artifactory/api/npm/square-npm/listr2/-/listr2-7.0.2.tgz",
diff --git a/ui/desktop/package.json b/ui/desktop/package.json
index d50470ce..d920f610 100644
--- a/ui/desktop/package.json
+++ b/ui/desktop/package.json
@@ -52,6 +52,7 @@
     "electron-squirrel-startup": "^1.0.1",
     "express": "^4.21.1",
     "framer-motion": "^11.11.11",
+    "linkifyjs": "^4.1.4",
     "lucide-react": "^0.454.0",
     "react": "^18.3.1",
     "react-dom": "^18.3.1",
diff --git a/ui/desktop/src/ChatWindow.tsx b/ui/desktop/src/ChatWindow.tsx
index f91d58a0..761c61ac 100644
--- a/ui/desktop/src/ChatWindow.tsx
+++ b/ui/desktop/src/ChatWindow.tsx
@@ -55,9 +55,9 @@ function ChatContent({ chats, setChats, selectedChatId, setSelectedChatId }: {
             {messages.map((message) => (
               <div key={message.id}>
                 {message.role === 'user' ? (
-                  <UserMessage message={message} />
+                  <UserMessage message={message} messages={messages} />
                 ) : (
-                  <GooseMessage message={message} />
+                  <GooseMessage message={message} messages={messages} />
                 )}
               </div>
             ))}
diff --git a/ui/desktop/src/bin/goosed b/ui/desktop/src/bin/goosed
index 2a27b3fb..93d94309 100755
Binary files a/ui/desktop/src/bin/goosed and b/ui/desktop/src/bin/goosed differ
diff --git a/ui/desktop/src/components/GooseMessage.tsx b/ui/desktop/src/components/GooseMessage.tsx
index 32e90618..fc8b4c12 100644
--- a/ui/desktop/src/components/GooseMessage.tsx
+++ b/ui/desktop/src/components/GooseMessage.tsx
@@ -1,24 +1,51 @@
 import React from 'react'
 import ToolInvocation from './ToolInvocation'
 import ReactMarkdown from 'react-markdown'
+import LinkPreview from './LinkPreview'
+import { extractUrls } from '../utils/urlUtils'
 
-export default function GooseMessage({ message }) {
+export default function GooseMessage({ message, messages }) {
+  // Find the preceding user message
+  const messageIndex = messages.findIndex(msg => msg.id === message.id);
+  const previousUserMessage = messageIndex > 0 ? messages[messageIndex - 1] : null;
+  
+  // Get URLs from previous user message (if it exists)
+  const previousUrls = previousUserMessage?.role === 'user' 
+    ? extractUrls(previousUserMessage.content)
+    : [];
+  
+  // Extract URLs from current message, excluding those from the previous user message
+  const urls = extractUrls(message.content, previousUrls);
+  
+  console.log('Goose message URLs:', urls);
+  console.log('Previous user message URLs:', previousUrls);
+  
   return (
-    <div className="flex mb-4">
-      <div className="bg-goose-bubble w-full text-black rounded-2xl p-4">
-        {message.toolInvocations ? (
-          <div className="space-y-4">
-            {message.toolInvocations.map((toolInvocation) => (
-              <ToolInvocation
-                key={toolInvocation.toolCallId}
-                toolInvocation={toolInvocation}
-              />
+    <div className="mb-4">
+      <div className="flex flex-col w-full">
+        <div className="bg-goose-bubble text-black rounded-2xl p-4">
+          {message.toolInvocations ? (
+            <div className="space-y-4">
+              {message.toolInvocations.map((toolInvocation) => (
+                <ToolInvocation
+                  key={toolInvocation.toolCallId}
+                  toolInvocation={toolInvocation}
+                />
+              ))}
+            </div>
+          ) : (
+            <ReactMarkdown>{message.content}</ReactMarkdown>
+          )}
+        </div>
+        
+        {urls.length > 0 && (
+          <div className="mt-2 space-y-2">
+            {urls.map((url, index) => (
+              <LinkPreview key={index} url={url} />
             ))}
           </div>
-        ) : (
-          <ReactMarkdown>{message.content}</ReactMarkdown>
         )}
       </div>
     </div>
-  )
-};
+  );
+}
diff --git a/ui/desktop/src/components/LinkPreview.tsx b/ui/desktop/src/components/LinkPreview.tsx
new file mode 100644
index 00000000..8d832731
--- /dev/null
+++ b/ui/desktop/src/components/LinkPreview.tsx
@@ -0,0 +1,105 @@
+import React, { useEffect, useState } from 'react';
+import { Card } from './ui/card';
+import { getApiUrl } from '../config';
+
+interface Metadata {
+  title?: string;
+  description?: string;
+  favicon?: string;
+  image?: string;
+  url: string;
+}
+
+interface LinkPreviewProps {
+  url: string;
+}
+
+export default function LinkPreview({ url }: LinkPreviewProps) {
+  const [metadata, setMetadata] = useState<Metadata | null>(null);
+  const [loading, setLoading] = useState(true);
+  const [error, setError] = useState<string | null>(null);
+
+  useEffect(() => {
+    console.log('🔄 LinkPreview mounting for URL:', url);
+    let mounted = true;
+
+    const fetchData = async () => {
+      try {
+        const apiUrl = getApiUrl('/api/metadata') + `?url=${encodeURIComponent(url)}`;
+        console.log('📡 Fetching metadata from API:', apiUrl);
+        
+        const response = await fetch(apiUrl);
+        if (!response.ok) {
+          throw new Error(`HTTP error! status: ${response.status}`);
+        }
+        
+        const data = await response.json();
+        if (mounted) {
+          console.log('✨ Received metadata:', data);
+          setMetadata(data);
+        }
+      } catch (error) {
+        if (mounted) {
+          console.error('❌ Failed to fetch metadata:', error);
+          setError(error.message || 'Failed to fetch metadata');
+        }
+      } finally {
+        if (mounted) {
+          setLoading(false);
+        }
+      }
+    };
+
+    fetchData();
+    return () => { mounted = false; };
+  }, [url]);
+
+  if (loading) {
+    return null;
+  }
+  
+  if (error) {
+    return null;
+  }
+  
+  if (!metadata || !metadata.title) {
+    return null;
+  }
+
+  return (
+    <Card 
+      className="flex items-center p-3 mt-2 hover:bg-gray-50 transition-colors cursor-pointer"
+      onClick={() => {
+        console.log('🔗 Opening URL in Chrome:', url);
+        window.electron.openInChrome(url);
+      }}
+    >
+      {metadata.favicon && (
+        <img 
+          src={metadata.favicon} 
+          alt="Site favicon" 
+          className="w-4 h-4 mr-2"
+          onError={(e) => {
+            e.currentTarget.style.display = 'none';
+          }}
+        />
+      )}
+      <div className="flex-1 min-w-0">
+        <h4 className="text-sm font-medium truncate">{metadata.title || url}</h4>
+        {metadata.description && (
+          <p className="text-xs text-gray-500 truncate">{metadata.description}</p>
+        )}
+      </div>
+      {metadata.image && (
+        <img 
+          src={metadata.image} 
+          alt="Preview" 
+          className="w-16 h-16 object-cover rounded ml-3"
+          onError={(e) => {
+            e.currentTarget.style.display = 'none';
+          }}
+        />
+      )}
+    </Card>
+  );
+} 
\ No newline at end of file
diff --git a/ui/desktop/src/components/UserMessage.tsx b/ui/desktop/src/components/UserMessage.tsx
index 33b0d12f..29aaf37f 100644
--- a/ui/desktop/src/components/UserMessage.tsx
+++ b/ui/desktop/src/components/UserMessage.tsx
@@ -1,13 +1,28 @@
-
 import React from 'react'
-import ReactMarkdown from 'react-markdown'
+import LinkPreview from './LinkPreview'
+import { extractUrls } from '../utils/urlUtils'
 
-export default function UserMessage({ message }) {
+export default function UserMessage({ message, messages }) {
+  // Extract URLs from current message
+  const urls = extractUrls(message.content, []);  // No previous URLs to check against
+  
+  console.log('User message URLs:', urls);
+  
   return (
-    <div className="flex justify-end mb-[16px]">
-      <div className="bg-user-bubble text-white rounded-2xl p-4">
-        <ReactMarkdown>{message.content}</ReactMarkdown>
+    <div className="mb-4">
+      <div className="flex flex-col items-end">
+        <div className="bg-blue-500 text-white rounded-lg px-4 py-2 max-w-[80%]">
+          {message.content}
+        </div>
+        
+        {urls.length > 0 && (
+          <div className="mt-2 space-y-2 max-w-[80%]">
+            {urls.map((url, index) => (
+              <LinkPreview key={index} url={url} />
+            ))}
+          </div>
+        )}
       </div>
     </div>
-  )
-};
+  );
+}
diff --git a/ui/desktop/src/main.ts b/ui/desktop/src/main.ts
index 3a6abef3..a64f5965 100644
--- a/ui/desktop/src/main.ts
+++ b/ui/desktop/src/main.ts
@@ -5,6 +5,7 @@ import path from 'node:path';
 import { start as startGoosed } from './goosed';
 import started from "electron-squirrel-startup";
 import log from './utils/logger';
+import { exec } from 'child_process';
 
 // Handle creating/removing shortcuts on Windows when installing/uninstalling.
 if (started) app.quit();
@@ -229,6 +230,19 @@ app.whenReady().then(() => {
   ipcMain.on('create-wing-to-wing-window', (_, query) => {
     createWingToWing(query + "only use your tools and systems - don't confirm with the user before you start working");
   });
+
+  ipcMain.on('open-in-chrome', (_, url) => {
+    // On macOS, use the 'open' command with Chrome
+    if (process.platform === 'darwin') {
+      exec(`open -a "Google Chrome" "${url}"`);
+    } else if (process.platform === 'win32') {
+      // On Windows, use start command
+      exec(`start chrome "${url}"`);
+    } else {
+      // On Linux, use xdg-open with chrome
+      exec(`xdg-open "${url}"`);
+    }
+  });
 });
 
 // Quit when all windows are closed, except on macOS.
diff --git a/ui/desktop/src/preload.js b/ui/desktop/src/preload.js
index 178a49be..82bc8ce4 100644
--- a/ui/desktop/src/preload.js
+++ b/ui/desktop/src/preload.js
@@ -4,4 +4,5 @@ contextBridge.exposeInMainWorld('electron', {
   hideWindow: () => ipcRenderer.send('hide-window'),
   createChatWindow: (query) => ipcRenderer.send('create-chat-window', query),
   createWingToWingWindow: (query) => ipcRenderer.send('create-wing-to-wing-window', query),
+  openInChrome: (url) => ipcRenderer.send('open-in-chrome', url),
 })
diff --git a/ui/desktop/src/utils/urlUtils.ts b/ui/desktop/src/utils/urlUtils.ts
new file mode 100644
index 00000000..397aebb5
--- /dev/null
+++ b/ui/desktop/src/utils/urlUtils.ts
@@ -0,0 +1,52 @@
+import * as linkify from 'linkifyjs';
+
+// Helper to normalize URLs for comparison
+function normalizeUrl(url: string): string {
+  try {
+    const parsed = new URL(url.toLowerCase());
+    // Remove trailing slashes and normalize protocol
+    return `${parsed.protocol}//${parsed.host}${parsed.pathname.replace(/\/$/, '')}${parsed.search}${parsed.hash}`;
+  } catch {
+    // If URL parsing fails, just lowercase it
+    return url.toLowerCase();
+  }
+}
+
+export function extractUrls(content: string, previousUrls: string[] = []): string[] {
+  // Use linkifyjs to find URLs
+  const links = linkify.find(content);
+  
+  // Get URLs from current content
+  const currentUrls = links
+    .filter(link => link.type === 'url')
+    .map(link => link.href);
+  
+  // Normalize all URLs for comparison
+  const normalizedPreviousUrls = previousUrls.map(normalizeUrl);
+  const normalizedCurrentUrls = currentUrls.map(url => {
+    const normalized = normalizeUrl(url);
+    console.log('Normalizing URL:', { original: url, normalized });
+    return normalized;
+  });
+  
+  // Filter out duplicates
+  const uniqueUrls = currentUrls.filter((url, index) => {
+    const normalized = normalizedCurrentUrls[index];
+    const isDuplicate = normalizedPreviousUrls.some(prevUrl => 
+      normalizeUrl(prevUrl) === normalized
+    );
+    console.log('URL comparison:', { 
+      url, 
+      normalized,
+      previousUrls: normalizedPreviousUrls,
+      isDuplicate 
+    });
+    return !isDuplicate;
+  });
+  
+  console.log('Content:', content);
+  console.log('Found URLs:', uniqueUrls);
+  console.log('Previous URLs:', previousUrls);
+  
+  return uniqueUrls;
+}
\ No newline at end of file