diff --git a/scripts/translations/.translation_state.json b/scripts/translations/.translation_state.json
index 81b72bd0ea..87c967532a 100644
--- a/scripts/translations/.translation_state.json
+++ b/scripts/translations/.translation_state.json
@@ -15539,7 +15539,6 @@
     "actions": {
       "actionsRefresh": "3cf8d66227384dc2",
       "aiChatClose": "a619ab8971872dcf",
-      "aiChatExpand": "cb569c3ed515eb89",
       "aiChatToggle": "e5000da4d3f67a4c",
       "aiToolsetsRefresh": "3cf8d66227384dc2",
       "alertDestinationsAdd": "d0eb0b5fd8a15847",
diff --git a/web/src/lib/vue-shortcut-manager/ShortcutCheatsheet.vue b/web/src/lib/vue-shortcut-manager/ShortcutCheatsheet.vue
index 4321b08e3e..99d1bb4ad7 100644
--- a/web/src/lib/vue-shortcut-manager/ShortcutCheatsheet.vue
+++ b/web/src/lib/vue-shortcut-manager/ShortcutCheatsheet.vue
@@ -261,6 +261,7 @@ const capabilities = computed<ShortcutCapabilities>(() => ({
   incidentsEnabled: Boolean(store.state.zoConfig?.incidents_enabled),
   modelPricingEnabled: Boolean(store.state.zoConfig?.model_pricing_enabled),
   rbacEnabled: Boolean(store.state.zoConfig?.rbac_enabled),
+  aiEnabled: Boolean(store.state.zoConfig?.ai_enabled),
 }));
 
 const open = computed({
@@ -315,11 +316,14 @@ const allModules = computed<DisplayModule[]>(() => {
       return [
         {
           title: t(group.pageKey, PAGE_TITLE_PARAMS[group.pageKey] ?? {}),
-          entries: group.shortcuts.map((s) => ({
-            id: s.id,
-            display: entryDisplay(s),
-            label: t(s.descriptionKey),
-          })),
+          entries: group.shortcuts
+            // Entry-level gate mirrors the feature's real availability (e.g. the AI chat shortcut only works on enterprise with ai_enabled).
+            .filter((s) => !s.visible || s.visible(caps))
+            .map((s) => ({
+              id: s.id,
+              display: entryDisplay(s),
+              label: t(s.descriptionKey),
+            })),
         },
       ];
     }),
diff --git a/web/src/lib/vue-shortcut-manager/__tests__/shortcutRegistry.spec.ts b/web/src/lib/vue-shortcut-manager/__tests__/shortcutRegistry.spec.ts
index 1ef4ec8f0c..3b1706c623 100644
--- a/web/src/lib/vue-shortcut-manager/__tests__/shortcutRegistry.spec.ts
+++ b/web/src/lib/vue-shortcut-manager/__tests__/shortcutRegistry.spec.ts
@@ -13,6 +13,7 @@ const OSS: ShortcutCapabilities = {
   incidentsEnabled: false,
   modelPricingEnabled: false,
   rbacEnabled: false,
+  aiEnabled: false,
 };
 const ENTERPRISE: ShortcutCapabilities = {
   isEnterprise: true,
@@ -22,6 +23,7 @@ const ENTERPRISE: ShortcutCapabilities = {
   incidentsEnabled: true,
   modelPricingEnabled: true,
   rbacEnabled: true,
+  aiEnabled: true,
 };
 const CLOUD: ShortcutCapabilities = {
   isEnterprise: false,
@@ -31,6 +33,7 @@ const CLOUD: ShortcutCapabilities = {
   incidentsEnabled: true,
   modelPricingEnabled: true,
   rbacEnabled: true,
+  aiEnabled: true,
 };
 
 /** Mirrors ShortcutCheatsheet: a page shows unless its gate rejects the caps. */
@@ -50,6 +53,15 @@ function visibleModuleTitles(caps: ShortcutCapabilities): string[] {
   );
 }
 
+/** Entry-level gate, mirroring ShortcutCheatsheet: an entry shows unless its own gate rejects the caps. */
+function entryVisible(id: string, caps: ShortcutCapabilities): boolean {
+  for (const g of SHORTCUT_REGISTRY) {
+    const e = g.shortcuts.find((s) => s.id === id);
+    if (e) return !e.visible || e.visible(caps);
+  }
+  throw new Error(`entry ${id} not registered`);
+}
+
 const GATED_IN_OSS = [
   "shortcuts.pages.searchSchedulers",
   "shortcuts.pages.alertSources",
@@ -177,3 +189,21 @@ describe("shortcut cheatsheet OSS gating", () => {
     expect(cloudNonMeta.has("shortcuts.pages.orgManagement")).toBe(false);
   });
 });
+
+describe("aiChatToggle entry visibility", () => {
+  it("is hidden on OSS (the shortcut is never registered there)", () => {
+    expect(entryVisible("aiChatToggle", OSS)).toBe(false);
+  });
+
+  it("is hidden on cloud — the AI chat shortcut is enterprise-only", () => {
+    expect(entryVisible("aiChatToggle", CLOUD)).toBe(false);
+  });
+
+  it("is hidden on enterprise when ai_enabled is off (the handler no-ops)", () => {
+    expect(entryVisible("aiChatToggle", { ...ENTERPRISE, aiEnabled: false })).toBe(false);
+  });
+
+  it("is shown only on enterprise with ai_enabled on", () => {
+    expect(entryVisible("aiChatToggle", ENTERPRISE)).toBe(true);
+  });
+});
diff --git a/web/src/lib/vue-shortcut-manager/shortcutRegistry.ts b/web/src/lib/vue-shortcut-manager/shortcutRegistry.ts
index 94fac4914c..93b5556950 100644
--- a/web/src/lib/vue-shortcut-manager/shortcutRegistry.ts
+++ b/web/src/lib/vue-shortcut-manager/shortcutRegistry.ts
@@ -42,6 +42,8 @@ export interface ShortcutEntry {
   display?: string;
   /** Fire even while a text input has focus (see `Shortcut.allowInInput`). */
   allowInInput?: boolean;
+  /** Hide this entry in the cheatsheet unless the edition/config exposes it. */
+  visible?: (caps: ShortcutCapabilities) => boolean;
 }
 
 export interface ShortcutGroup {
@@ -63,6 +65,7 @@ export interface ShortcutCapabilities {
   incidentsEnabled: boolean;
   modelPricingEnabled: boolean;
   rbacEnabled: boolean;
+  aiEnabled: boolean;
 }
 
 export interface ShortcutModule {
@@ -86,6 +89,7 @@ const incidents = (c: ShortcutCapabilities) => enterpriseOrCloud(c) && c.inciden
 const onlineEvals = (c: ShortcutCapabilities) => enterpriseOrCloud(c) && c.onlineEvalsEnabled;
 const modelPricing = (c: ShortcutCapabilities) => enterpriseOrCloud(c) && c.modelPricingEnabled;
 const rbac = (c: ShortcutCapabilities) => enterpriseOrCloud(c) && c.rbacEnabled;
+const aiChat = (c: ShortcutCapabilities) => c.isEnterprise && c.aiEnabled;
 // Cluster-scoped admin surfaces only render inside the _meta org.
 const metaAdmin = (c: ShortcutCapabilities) => c.isEnterprise && c.isMetaOrg;
 const cloudMetaAdmin = (c: ShortcutCapabilities) => c.isCloud && c.isMetaOrg;
@@ -207,6 +211,7 @@ export const SHORTCUT_REGISTRY: ShortcutGroup[] = [
         keyForWindows: "ctrl+b",
         keyForMac: "meta+b",
         descriptionKey: "shortcuts.actions.aiChatToggle",
+        visible: aiChat,
       },
     ],
   },
diff --git a/web/src/locales/languages/ar-SA.json b/web/src/locales/languages/ar-SA.json
index 36f57978db..8e61c1c6f9 100644
--- a/web/src/locales/languages/ar-SA.json
+++ b/web/src/locales/languages/ar-SA.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "تحديث قائمة الرموز",
       "aiChatToggle": "تبديل دردشة الذكاء الاصطناعي",
       "aiChatClose": "إغلاق دردشة الذكاء الاصطناعي",
-      "aiChatExpand": "توسيع/تقويم دردشة الذكاء الاصطناعي",
       "logsSaveView": "عرض حفظ كملف محفوظ",
       "logsExport": "نتائج التصدير CSV",
       "tracesCopyUrl": "رابط مشاركة التتبع للنسخ",
diff --git a/web/src/locales/languages/de-DE.json b/web/src/locales/languages/de-DE.json
index c17e149634..76656fa04b 100644
--- a/web/src/locales/languages/de-DE.json
+++ b/web/src/locales/languages/de-DE.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Tokenliste aktualisieren",
       "aiChatToggle": "KI-Chat umschalten",
       "aiChatClose": "KI-Chat schließen",
-      "aiChatExpand": "KI-Chat erweitern/einklappen",
       "logsSaveView": "Als gespeicherte Ansicht speichern",
       "logsExport": "Ergebnisse als CSV exportieren",
       "tracesCopyUrl": "Trace-Share-URL kopieren",
diff --git a/web/src/locales/languages/en-US.json b/web/src/locales/languages/en-US.json
index 533cc951c4..c30b820a61 100644
--- a/web/src/locales/languages/en-US.json
+++ b/web/src/locales/languages/en-US.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Refresh token list",
       "aiChatToggle": "Toggle AI chat",
       "aiChatClose": "Close AI chat",
-      "aiChatExpand": "Expand/collapse AI chat",
       "logsSaveView": "Save as saved view",
       "logsExport": "Export results as CSV",
       "tracesCopyUrl": "Copy trace share URL",
diff --git a/web/src/locales/languages/es-ES.json b/web/src/locales/languages/es-ES.json
index 6b3e7d66ce..e9811aa609 100644
--- a/web/src/locales/languages/es-ES.json
+++ b/web/src/locales/languages/es-ES.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Actualizar lista de tokens",
       "aiChatToggle": "Alternar el chat de IA",
       "aiChatClose": "Cerrar chat de IA",
-      "aiChatExpand": "Expandir/contraer chat de IA",
       "logsSaveView": "Guardar como vista guardada",
       "logsExport": "Exportar los resultados como CSV",
       "tracesCopyUrl": "Copiar URL para compartir la traza",
diff --git a/web/src/locales/languages/fr-FR.json b/web/src/locales/languages/fr-FR.json
index 5c25f49508..dda498ec55 100644
--- a/web/src/locales/languages/fr-FR.json
+++ b/web/src/locales/languages/fr-FR.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Actualiser la liste des jetons",
       "aiChatToggle": "Activer/désactiver le chat IA",
       "aiChatClose": "Fermer le chat IA",
-      "aiChatExpand": "Développer/réduire le chat IA",
       "logsSaveView": "Enregistrer en tant que vue enregistrée",
       "logsExport": "Exporter les résultats au format CSV",
       "tracesCopyUrl": "Copier l'URL de partage de la trace",
diff --git a/web/src/locales/languages/it-IT.json b/web/src/locales/languages/it-IT.json
index 15b23c826e..986971c45c 100644
--- a/web/src/locales/languages/it-IT.json
+++ b/web/src/locales/languages/it-IT.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Aggiorna elenco token",
       "aiChatToggle": "Attiva la chat AI",
       "aiChatClose": "Chiudi chat AI",
-      "aiChatExpand": "Espandi/comprimi chat AI",
       "logsSaveView": "Salva come visualizzazione salvata",
       "logsExport": "Esporta i risultati in formato CSV",
       "tracesCopyUrl": "Copia URL di condivisione della traccia",
diff --git a/web/src/locales/languages/ja-JP.json b/web/src/locales/languages/ja-JP.json
index feadf149a0..4324e608db 100644
--- a/web/src/locales/languages/ja-JP.json
+++ b/web/src/locales/languages/ja-JP.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "トークンリストを更新",
       "aiChatToggle": "AI チャットを切り替える",
       "aiChatClose": "AI チャットを閉じる",
-      "aiChatExpand": "AI チャットを展開/折りたたむ",
       "logsSaveView": "保存済みビューとして保存",
       "logsExport": "結果を CSV としてエクスポート",
       "tracesCopyUrl": "トレース共有URLをコピー",
diff --git a/web/src/locales/languages/ko-KR.json b/web/src/locales/languages/ko-KR.json
index f1c50af176..be7cd90bd6 100644
--- a/web/src/locales/languages/ko-KR.json
+++ b/web/src/locales/languages/ko-KR.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "토큰 목록 새로고침",
       "aiChatToggle": "AI 채팅 켜기/끄기",
       "aiChatClose": "AI 채팅 닫기",
-      "aiChatExpand": "AI 채팅 펼치기/접기",
       "logsSaveView": "저장된 뷰로 저장",
       "logsExport": "결과를 CSV로 내보내기",
       "tracesCopyUrl": "트레이스 공유 URL 복사",
diff --git a/web/src/locales/languages/nl-NL.json b/web/src/locales/languages/nl-NL.json
index 59c2ed3583..4e2f747454 100644
--- a/web/src/locales/languages/nl-NL.json
+++ b/web/src/locales/languages/nl-NL.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Tokenlijst vernieuwen",
       "aiChatToggle": "AI-chat inschakelen",
       "aiChatClose": "AI-chat sluiten",
-      "aiChatExpand": "AI-chat uitvouwen/invouwen",
       "logsSaveView": "Opslaan als opgeslagen weergave",
       "logsExport": "Exporteer resultaten als CSV",
       "tracesCopyUrl": "Kopieer trace-deel-URL",
diff --git a/web/src/locales/languages/pl-PL.json b/web/src/locales/languages/pl-PL.json
index d63e476ca9..3f57ac0de1 100644
--- a/web/src/locales/languages/pl-PL.json
+++ b/web/src/locales/languages/pl-PL.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Odśwież listę tokenów",
       "aiChatToggle": "Przełącz czat AI",
       "aiChatClose": "Zamknij czat AI",
-      "aiChatExpand": "Rozwiń/zwiń czat AI",
       "logsSaveView": "Zapisz jako zapisany widok",
       "logsExport": "Eksportuj wyniki jako CSV",
       "tracesCopyUrl": "Kopiuj URL do udostępnienia śladu",
diff --git a/web/src/locales/languages/pt-PT.json b/web/src/locales/languages/pt-PT.json
index 0b373f7b48..574c17d03e 100644
--- a/web/src/locales/languages/pt-PT.json
+++ b/web/src/locales/languages/pt-PT.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Atualizar lista de tokens",
       "aiChatToggle": "Alternar bate-papo com IA",
       "aiChatClose": "Fechar chat de IA",
-      "aiChatExpand": "Expandir/recolher chat de IA",
       "logsSaveView": "Salvar como visualização salva",
       "logsExport": "Exportar resultados como CSV",
       "tracesCopyUrl": "Copiar URL de compartilhamento do rastreamento",
diff --git a/web/src/locales/languages/ru-RU.json b/web/src/locales/languages/ru-RU.json
index 46f3c79454..10c3632557 100644
--- a/web/src/locales/languages/ru-RU.json
+++ b/web/src/locales/languages/ru-RU.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Обновить список токенов",
       "aiChatToggle": "Переключить AI-чат",
       "aiChatClose": "Закрыть чат ИИ",
-      "aiChatExpand": "Развернуть/свернуть чат ИИ",
       "logsSaveView": "Сохранить как сохранённое представление",
       "logsExport": "Экспортировать результаты в CSV",
       "tracesCopyUrl": "Скопировать общую ссылку на трассировку",
diff --git a/web/src/locales/languages/tr-TR.json b/web/src/locales/languages/tr-TR.json
index 0ddfe7a397..2dd2e09d23 100644
--- a/web/src/locales/languages/tr-TR.json
+++ b/web/src/locales/languages/tr-TR.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Belirteç listesini yenile",
       "aiChatToggle": "AI sohbetini aç/kapat",
       "aiChatClose": "AI sohbetini kapat",
-      "aiChatExpand": "AI sohbetini genişlet/daralt",
       "logsSaveView": "Kayıtlı görünüm olarak kaydet",
       "logsExport": "Sonuçları CSV olarak dışa aktarın",
       "tracesCopyUrl": "İz paylaşım URL'sini kopyala",
diff --git a/web/src/locales/languages/vi-VN.json b/web/src/locales/languages/vi-VN.json
index 4ee9970c41..c6464e388a 100644
--- a/web/src/locales/languages/vi-VN.json
+++ b/web/src/locales/languages/vi-VN.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "Làm mới danh sách token",
       "aiChatToggle": "Bật/tắt trò chuyện AI",
       "aiChatClose": "Đóng trò chuyện AI",
-      "aiChatExpand": "Mở rộng/thu gọn trò chuyện AI",
       "logsSaveView": "Lưu dưới dạng chế độ xem đã lưu",
       "logsExport": "Xuất kết quả dưới dạng CSV",
       "tracesCopyUrl": "Sao chép URL chia sẻ dấu vết",
diff --git a/web/src/locales/languages/zh-CN.json b/web/src/locales/languages/zh-CN.json
index ced65c508d..ec9c420490 100644
--- a/web/src/locales/languages/zh-CN.json
+++ b/web/src/locales/languages/zh-CN.json
@@ -15164,7 +15164,6 @@
       "syntheticsTokensRefresh": "刷新令牌列表",
       "aiChatToggle": "切换 AI 聊天",
       "aiChatClose": "关闭 AI 聊天",
-      "aiChatExpand": "展开/折叠 AI 聊天",
       "logsSaveView": "另存为已保存视图",
       "logsExport": "将结果导出为 CSV",
       "tracesCopyUrl": "复制追踪分享链接",
diff --git a/web/src/locales/languages/zh-TW.json b/web/src/locales/languages/zh-TW.json
index 6c7e779185..5efe2e180b 100644
--- a/web/src/locales/languages/zh-TW.json
+++ b/web/src/locales/languages/zh-TW.json
@@ -15159,7 +15159,6 @@
       "syntheticsTokensRefresh": "重新整理 Token 清單",
       "aiChatToggle": "切換AI聊天",
       "aiChatClose": "關閉 AI 聊天",
-      "aiChatExpand": "展開/收合 AI 聊天",
       "logsSaveView": "另存為已儲存檢視",
       "logsExport": "匯出結果為CSV",
       "tracesCopyUrl": "複製追蹤分享網址",