diff --git a/src/adapters/inbound/ui/SidecarPanelAdapter.ts b/src/adapters/inbound/ui/SidecarPanelAdapter.ts
index 995acf8..8b94e7f 100644
--- a/src/adapters/inbound/ui/SidecarPanelAdapter.ts
+++ b/src/adapters/inbound/ui/SidecarPanelAdapter.ts
@@ -239,8 +239,8 @@ export class SidecarPanelAdapter {
                         await this.handleOpenHNStory(message.url);
                         break;
                     case 'openHNStoryInPanel':
-                        // Use new content view system instead of separate panel
-                        this.panelStateManager?.openContentView(message.url, message.title);
+                        // Check if URL can be embedded, otherwise open externally
+                        await this.handleOpenHNStoryInPanel(message.url, message.title);
                         break;
                     case 'openContentView':
                         this.panelStateManager?.openContentView(message.url, message.title);
@@ -756,6 +756,72 @@ export class SidecarPanelAdapter {
         await vscode.env.openExternal(vscode.Uri.parse(hnUrl));
     }
 
+    /**
+     * Check if a URL can be embedded in an iframe
+     * Returns true if the URL allows iframe embedding, false otherwise
+     */
+    private async checkIframeEmbeddable(url: string): Promise<boolean> {
+        try {
+            // Use native fetch with HEAD request to check headers
+            const controller = new AbortController();
+            const timeoutId = setTimeout(() => controller.abort(), 5000);
+
+            const response = await fetch(url, {
+                method: 'HEAD',
+                signal: controller.signal,
+                redirect: 'follow',
+            });
+
+            clearTimeout(timeoutId);
+
+            // Check X-Frame-Options header
+            const xFrameOptions = response.headers.get('x-frame-options');
+            if (xFrameOptions) {
+                const value = xFrameOptions.toLowerCase();
+                if (value === 'deny' || value === 'sameorigin') {
+                    return false;
+                }
+            }
+
+            // Check Content-Security-Policy frame-ancestors directive
+            const csp = response.headers.get('content-security-policy');
+            if (csp) {
+                const frameAncestorsMatch = csp.match(/frame-ancestors\s+([^;]+)/i);
+                if (frameAncestorsMatch) {
+                    const ancestors = frameAncestorsMatch[1].toLowerCase().trim();
+                    // 'none' or 'self' means no external embedding
+                    if (ancestors === "'none'" || ancestors === "'self'") {
+                        return false;
+                    }
+                }
+            }
+
+            return true;
+        } catch {
+            // On error (timeout, network issues), assume embeddable and let iframe handle it
+            return true;
+        }
+    }
+
+    /**
+     * Handle opening HN story in panel or external browser
+     * Checks if the URL can be embedded in iframe, opens externally if not
+     */
+    private async handleOpenHNStoryInPanel(url: string, title: string): Promise<void> {
+        if (!url) return;
+
+        const canEmbed = await this.checkIframeEmbeddable(url);
+        if (canEmbed) {
+            this.panelStateManager?.openContentView(url, title);
+        } else {
+            // Open in external browser and show notification
+            await vscode.env.openExternal(vscode.Uri.parse(url));
+            vscode.window.showInformationMessage(
+                `"${title}" opened in browser (site blocks iframe embedding)`
+            );
+        }
+    }
+
     private escapeHtml(text: string): string {
         return text
             .replace(/&/g, '&amp;')
diff --git a/src/adapters/inbound/ui/webview/core/App.ts b/src/adapters/inbound/ui/webview/core/App.ts
index a3c9f1a..9b5a89a 100644
--- a/src/adapters/inbound/ui/webview/core/App.ts
+++ b/src/adapters/inbound/ui/webview/core/App.ts
@@ -828,11 +828,84 @@ function renderContentViewState(contentView: ContentView): void {
   }
 
   if (iframe) {
+    // Track if content loaded successfully
+    let loadSuccessful = false;
+    let loadTimeout: ReturnType<typeof setTimeout> | null = null;
+
+    const showError = () => {
+      const loading = document.getElementById('content-loading');
+      const error = document.getElementById('content-error');
+      if (loading) loading.classList.add('hidden');
+      if (error) error.classList.remove('hidden');
+      iframe.style.display = 'none';
+    };
+
+    const showContent = () => {
+      loadSuccessful = true;
+      if (loadTimeout) {
+        clearTimeout(loadTimeout);
+        loadTimeout = null;
+      }
+      const loading = document.getElementById('content-loading');
+      if (loading) loading.classList.add('hidden');
+      iframe.style.display = 'block';
+    };
+
+    // Set a timeout to detect if iframe fails to load (X-Frame-Options, CSP blocks)
+    // Many sites block iframe embedding but don't trigger error events
+    loadTimeout = setTimeout(() => {
+      if (!loadSuccessful) {
+        // After timeout, check if iframe has any accessible content
+        try {
+          // Try to access iframe content - will throw for blocked/cross-origin frames
+          const doc = iframe.contentDocument;
+          // If we can access and it's empty or about:blank, likely blocked
+          if (doc && (doc.body?.innerHTML === '' || doc.URL === 'about:blank')) {
+            showError();
+            return;
+          }
+          // If accessible and has content, show it
+          if (doc && doc.body?.innerHTML) {
+            showContent();
+            return;
+          }
+          // Cross-origin but might be loaded - give benefit of doubt
+          showContent();
+        } catch {
+          // Cross-origin access denied - this is normal for loaded external sites
+          // The iframe might still be showing content, so show it
+          showContent();
+        }
+      }
+    }, 5000);
+
     iframe.addEventListener(
       'load',
       () => {
-        const loading = document.getElementById('content-loading');
-        if (loading) loading.classList.add('hidden');
+        // iframe loaded - but might be empty if blocked by X-Frame-Options
+        // Check if we can detect empty content
+        setTimeout(() => {
+          try {
+            const doc = iframe.contentDocument;
+            // If we can access the document and it's essentially empty, likely blocked
+            if (doc) {
+              const bodyContent = doc.body?.innerHTML?.trim() || '';
+              const hasContent = bodyContent.length > 0 && doc.URL !== 'about:blank';
+              if (hasContent) {
+                showContent();
+              } else {
+                // Empty content likely means blocked
+                showError();
+              }
+            } else {
+              // Can't access document (cross-origin) - assume loaded successfully
+              showContent();
+            }
+          } catch {
+            // Cross-origin access denied - iframe is loaded with external content
+            showContent();
+          }
+        }, 100);
       },
       { signal: getSignal() }
     );
@@ -840,10 +913,11 @@ function renderContentViewState(contentView: ContentView): void {
     iframe.addEventListener(
       'error',
       () => {
-        const loading = document.getElementById('content-loading');
-        const error = document.getElementById('content-error');
-        if (loading) loading.classList.add('hidden');
-        if (error) error.classList.remove('hidden');
+        if (loadTimeout) {
+          clearTimeout(loadTimeout);
+          loadTimeout = null;
+        }
+        showError();
       },
       { signal: getSignal() }
     );