diff --git a/browser-extension/popup/popup.js b/browser-extension/popup/popup.js
index 8c7ae997..22f82558 100644
--- a/browser-extension/popup/popup.js
+++ b/browser-extension/popup/popup.js
@@ -109,18 +109,22 @@ sendFileBtn.addEventListener('click', async () => {
             credentials: 'include'
         });
         
-        const result = await response.json();
-        
         if (response.ok) {
+            const result = await response.json();
             showStatus(
                 `✓ File sent successfully! Task ID: ${result.task_id}\nFilename: ${result.filename}`,
                 'success'
             );
         } else {
-            showStatus(
-                `Error: ${result.detail || 'Failed to send file'}`,
-                'error'
-            );
+            // Try to parse JSON error, fall back to status text
+            let errorMessage = 'Failed to send file';
+            try {
+                const result = await response.json();
+                errorMessage = result.detail || errorMessage;
+            } catch (e) {
+                errorMessage = `HTTP ${response.status}: ${response.statusText}`;
+            }
+            showStatus(`Error: ${errorMessage}`, 'error');
         }
     } catch (error) {
         showStatus(
diff --git a/browser-extension/scripts/background.js b/browser-extension/scripts/background.js
index 90f90eaa..8fc110da 100644
--- a/browser-extension/scripts/background.js
+++ b/browser-extension/scripts/background.js
@@ -4,13 +4,18 @@
 chrome.runtime.onInstalled.addListener((details) => {
     if (details.reason === 'install') {
         console.log('DocuElevate extension installed');
-        // Open options page on first install
-        chrome.tabs.create({
-            url: chrome.runtime.getURL('popup/popup.html')
-        });
+        // Note: We don't open the popup automatically to avoid poor UX
+        // User can click the extension icon to configure
     } else if (details.reason === 'update') {
         console.log('DocuElevate extension updated');
     }
+    
+    // Create context menu item
+    chrome.contextMenus.create({
+        id: 'send-to-docuelevate',
+        title: 'Send to DocuElevate',
+        contexts: ['link', 'page']
+    });
 });
 
 // Listen for messages from content script or popup
@@ -59,15 +64,6 @@ async function handleSendUrl(data) {
     return await response.json();
 }
 
-// Add context menu item for sending URLs
-chrome.runtime.onInstalled.addListener(() => {
-    chrome.contextMenus.create({
-        id: 'send-to-docuelevate',
-        title: 'Send to DocuElevate',
-        contexts: ['link', 'page']
-    });
-});
-
 // Handle context menu clicks
 chrome.contextMenus.onClicked.addListener(async (info, tab) => {
     if (info.menuItemId === 'send-to-docuelevate') {
diff --git a/browser-extension/scripts/content.js b/browser-extension/scripts/content.js
index 89db0e3b..72face41 100644
--- a/browser-extension/scripts/content.js
+++ b/browser-extension/scripts/content.js
@@ -12,9 +12,7 @@ chrome.runtime.onMessage.addListener((message, sender, sendResponse) => {
             title: document.title
         };
         sendResponse(pageInfo);
-        return true; // Indicates response will be sent asynchronously
     }
-    return false; // No async response
 });
 
 // Detect if current page is a direct file link