diff --git a/apps/web/src/components/layout/sidebar.tsx b/apps/web/src/components/layout/sidebar.tsx
index d5b7d820..7383ae1f 100644
--- a/apps/web/src/components/layout/sidebar.tsx
+++ b/apps/web/src/components/layout/sidebar.tsx
@@ -10,9 +10,10 @@
  * - 單色圖示
  *
  * IA D0 (2026-06-27):
- * - 側欄只放高頻 primary 工作台。
- * - Runs / Approvals / Contracts 等流程細節保留深連結，不再攤平成主導航。
- * - 頁面內以同頁 sections 呈現關鍵狀態，減少二層分頁藏內容。
+ * - 側欄保留 primary 工作台與 secondary 深連結。
+ * - Runs / Approvals / Contracts / Alerts 等流程細節以二級樣式顯示，
+ *   避免路由被移除後只剩隱藏連結。
+ * - 頁面內仍以同頁 sections 呈現關鍵狀態，減少二層分頁藏內容。
  *
  * Phase 19: 使用 Z_INDEX.SIDEBAR (40)
  * @see lib/constants/z-index.ts
@@ -126,8 +127,7 @@ export function Sidebar({
       {/* 導航列表 - Operator workflow sections */}
       <nav className="flex-1 py-2 overflow-y-auto">
         {PRODUCT_NAV_SECTIONS.map(section => {
-          const visibleItems = section.items.filter(item => item.surface !== 'secondary')
-          if (visibleItems.length === 0) return null
+          if (section.items.length === 0) return null
 
           return (
           <div key={section.sectionKey} style={{ marginBottom: 4 }}>
@@ -145,9 +145,10 @@ export function Sidebar({
                 {tSection(section.sectionKey)}
               </div>
             )}
-            {visibleItems.map(item => {
+            {section.items.map(item => {
               const active = isActive(item)
               const count = item.badge && mounted ? pendingCount : 0
+              const secondary = item.surface === 'secondary'
               return (
                 <Link
                   key={item.id}
@@ -157,21 +158,21 @@ export function Sidebar({
                   style={{
                     display: 'flex',
                     alignItems: 'center',
-                    gap: collapsed ? 0 : 8,
+                    gap: collapsed ? 0 : secondary ? 7 : 8,
                     justifyContent: collapsed ? 'center' : 'flex-start',
-                    padding: collapsed ? '8px 0' : '6px 12px',
-                    fontSize: 14,
-                    color: active ? '#141413' : '#87867f',
+                    padding: collapsed ? '8px 0' : secondary ? '4px 12px 4px 30px' : '6px 12px',
+                    fontSize: secondary ? 13 : 14,
+                    color: active ? '#141413' : secondary ? '#77736a' : '#87867f',
                     fontWeight: active ? 600 : 400,
                     borderRight: active ? '2px solid #d97757' : '2px solid transparent',
                     background: active ? 'rgba(217,119,87,0.08)' : 'transparent',
                     textDecoration: 'none',
                     transition: 'all 0.15s',
                     position: 'relative' as const,
-                    minHeight: collapsed ? 36 : 32,
+                    minHeight: collapsed ? 36 : secondary ? 28 : 32,
                   }}
                 >
-                  <item.Icon size={15} aria-hidden="true" />
+                  <item.Icon size={secondary ? 14 : 15} aria-hidden="true" />
                   {!collapsed && (
                     <span style={{ minWidth: 0, overflowWrap: 'anywhere' }}>
                       {t(item.labelKey)}
diff --git a/apps/web/src/lib/__tests__/product-ia.test.ts b/apps/web/src/lib/__tests__/product-ia.test.ts
new file mode 100644
index 00000000..5c1cd6b3
--- /dev/null
+++ b/apps/web/src/lib/__tests__/product-ia.test.ts
@@ -0,0 +1,27 @@
+import { describe, expect, it } from 'vitest'
+
+import { PRODUCT_NAV_SECTIONS } from '../navigation/product-ia'
+
+const navIds = PRODUCT_NAV_SECTIONS.flatMap(section => section.items.map(item => item.id))
+
+describe('product IA navigation', () => {
+  it('keeps secondary operational routes visible in the canonical nav map', () => {
+    expect(navIds).toEqual(expect.arrayContaining([
+      'awooop-runs',
+      'awooop-approvals',
+      'awooop-contracts',
+      'alerts',
+      'reports',
+      'terminal',
+      'classic',
+    ]))
+  })
+
+  it('keeps IwoooS related security routes integrated instead of removing them', () => {
+    expect(navIds).toEqual(expect.arrayContaining([
+      'iwooos-security',
+      'iwooos-security-compliance',
+      'governance-security',
+    ]))
+  })
+})
diff --git a/apps/web/src/lib/navigation/product-ia.ts b/apps/web/src/lib/navigation/product-ia.ts
index b6065f4f..1da2c227 100644
--- a/apps/web/src/lib/navigation/product-ia.ts
+++ b/apps/web/src/lib/navigation/product-ia.ts
@@ -134,8 +134,21 @@ export const PRODUCT_NAV_SECTIONS: ProductNavSection[] = [
         href: '/iwooos',
         labelKey: 'iwooos',
         Icon: ShieldCheck,
-        aliases: ['/security-compliance'],
-        relatedPaths: ['/security', '/compliance', '/governance'],
+      },
+      {
+        id: 'iwooos-security-compliance',
+        href: '/security-compliance',
+        labelKey: 'iwooosSecurityCompliance',
+        Icon: ShieldCheck,
+        aliases: ['/security', '/compliance'],
+        surface: 'secondary',
+      },
+      {
+        id: 'governance-security',
+        href: '/governance',
+        labelKey: 'governanceSecurity',
+        Icon: Radar,
+        surface: 'secondary',
       },
       {
         id: 'operations',