diff --git a/extension/src/background/index.ts b/extension/src/background/index.ts
index 4fea757..6ba46b3 100644
--- a/extension/src/background/index.ts
+++ b/extension/src/background/index.ts
@@ -9,7 +9,19 @@ const API_BASE = import.meta.env.VITE_API_BASE_URL || 'http://localhost:8080/api
 
 chrome.runtime.onMessage.addListener((message: { type: string; payload?: any }, _sender: chrome.runtime.MessageSender, sendResponse: (response?: any) => void) => {
     if (message.type === 'SHOW_INSIGHT') {
-        console.log('Received tweet data in background:', message.payload);
+        console.log('[InsightReply Background] Received SHOW_INSIGHT data:', message.payload);
+        if (_sender.tab?.id) {
+            console.log(`[InsightReply Background] Forwarding SHOW_INSIGHT to tab ${_sender.tab.id}`);
+            chrome.tabs.sendMessage(_sender.tab.id, message, (response) => {
+                if (chrome.runtime.lastError) {
+                    console.error('[InsightReply Background] Error forwarding message to tab:', chrome.runtime.lastError);
+                } else {
+                    console.log('[InsightReply Background] Successfully forwarded to tab, response:', response);
+                }
+            });
+        }
+        sendResponse({ success: true, forwarded: !!_sender.tab?.id });
+        return true;
     }
 
     if (message.type === 'FETCH_CUSTOM_STRATEGIES') {
diff --git a/extension/src/content/index.ts b/extension/src/content/index.ts
index de75472..ec88edb 100644
--- a/extension/src/content/index.ts
+++ b/extension/src/content/index.ts
@@ -52,7 +52,14 @@ const extractTweetData = (tweetElement: HTMLElement): TweetData | null => {
         const authorElement = tweetElement.querySelector('[data-testid="User-Name"]');
         const linkElement = tweetElement.querySelector('time')?.parentElement as HTMLAnchorElement;
 
-        if (!textElement || !authorElement || !linkElement) return null;
+        if (!textElement || !authorElement || !linkElement) {
+            console.debug('[InsightReply] Missing elements for tweet extraction:', {
+                hasText: !!textElement,
+                hasAuthor: !!authorElement,
+                hasLink: !!linkElement
+            });
+            return null;
+        }
 
         const getStat = (testid: string) => {
             const el = tweetElement.querySelector(`[data-testid="${testid}"]`);
@@ -146,19 +153,40 @@ const injectInsightButton = (tweetElement: HTMLElement) => {
     btnContainer.style.marginLeft = '12px';
     btnContainer.style.cursor = 'pointer';
 
-    btnContainer.innerHTML = `
-    <div style="padding: 4px; border-radius: 9999px; transition: background 0.2s;" onmouseover="this.style.background='rgba(139, 92, 246, 0.1)'" onmouseout="this.style.background='transparent'">
+    const innerDiv = document.createElement('div');
+    innerDiv.style.cssText = 'padding: 4px; border-radius: 9999px; transition: background 0.2s;';
+
+    // Use event listeners instead of inline handlers to comply with Content Security Policy
+    innerDiv.addEventListener('mouseover', () => {
+        innerDiv.style.background = 'rgba(139, 92, 246, 0.1)';
+    });
+    innerDiv.addEventListener('mouseout', () => {
+        innerDiv.style.background = 'transparent';
+    });
+
+    innerDiv.innerHTML = `
       <svg viewBox="0 0 24 24" width="20" height="20" fill="currentColor" style="color: #8B5CF6;">
         <path d="M12 2C6.48 2 2 6.48 2 12s4.48 10 10 10 10-4.48 10-10S17.52 2 12 2zm1 15h-2v-2h2v2zm0-4h-2V7h2v6z"></path>
       </svg>
-    </div>
-  `;
+    `;
+    btnContainer.appendChild(innerDiv);
 
     btnContainer.onclick = (e) => {
         e.stopPropagation();
+        e.preventDefault();
+        console.log('[InsightReply] Insight button clicked');
+
         const data = extractTweetData(tweetElement);
         if (data) {
-            chrome.runtime.sendMessage({ type: 'SHOW_INSIGHT', payload: data });
+            console.log('[InsightReply] Extracted Tweet Data:', data);
+            chrome.runtime.sendMessage({ type: 'SHOW_INSIGHT', payload: data }, (response) => {
+                console.log('[InsightReply] Background script responsed SHOW_INSIGHT with:', response);
+                if (chrome.runtime.lastError) {
+                    console.error('[InsightReply] Error sending SHOW_INSIGHT message:', chrome.runtime.lastError);
+                }
+            });
+        } else {
+            console.warn('[InsightReply] Failed to extract tweet data on click');
         }
     };
 
diff --git a/extension/src/content/sidebar-mount.ts b/extension/src/content/sidebar-mount.ts
index ad5efb5..f7e8bd1 100644
--- a/extension/src/content/sidebar-mount.ts
+++ b/extension/src/content/sidebar-mount.ts
@@ -44,8 +44,11 @@ function initSidebar(tweetData?: any) {
 }
 
 // Listen for messages to show/hide or update data
-chrome.runtime.onMessage.addListener((message) => {
+chrome.runtime.onMessage.addListener((message, _sender, sendResponse) => {
     if (message.type === 'SHOW_INSIGHT') {
-        initSidebar(message.payload)
+        console.log('[InsightReply Sidebar Mount] Received SHOW_INSIGHT message:', message.payload);
+        initSidebar(message.payload);
+        sendResponse({ received: true });
     }
+    return true;
 });