diff --git a/docs/release-control/v6/internal/subsystems/ai-runtime.md b/docs/release-control/v6/internal/subsystems/ai-runtime.md
index 0abba367f..18f80d778 100644
--- a/docs/release-control/v6/internal/subsystems/ai-runtime.md
+++ b/docs/release-control/v6/internal/subsystems/ai-runtime.md
@@ -122,9 +122,9 @@ runtime cost control, and shared AI transport surfaces.
    provider route to a configured gateway or alternate model without losing the
    draft or creating a parallel picker. When the same model is available through
    another configured provider route, the failed turn must offer that route as a
-   direct one-click action before falling back to the general model selector.
-   Retry remains available, but it must not be the only visible action when a
-   failed Assistant turn is shown.
+   direct one-click route-and-retry action before falling back to the general
+   model selector. Retry remains available, but it must not be the only visible
+   action when a failed Assistant turn is shown.
    Restored Assistant sessions must hydrate saved assistant content and
    persisted tool calls into the same transcript event shape used by live
    streams so switching sessions does not hide prior tool evidence or collapse
diff --git a/frontend-modern/src/components/AI/Chat/ChatMessages.tsx b/frontend-modern/src/components/AI/Chat/ChatMessages.tsx
index 93934e84f..5bae36d0f 100644
--- a/frontend-modern/src/components/AI/Chat/ChatMessages.tsx
+++ b/frontend-modern/src/components/AI/Chat/ChatMessages.tsx
@@ -22,7 +22,7 @@ interface ChatMessagesProps {
   onRetry?: (messageId: string) => void;
   onChangeModel?: () => void;
   getModelRouteAlternative?: (message: ChatMessage) => ModelRouteRecoveryOption | null;
-  onUseModelRoute?: (modelId: string) => void;
+  onUseModelRoute?: (modelId: string, messageId?: string) => void;
   // Dashboard props
   recentSessions?: ChatSession[];
   onLoadSession?: (sessionId: string) => void;
diff --git a/frontend-modern/src/components/AI/Chat/MessageItem.tsx b/frontend-modern/src/components/AI/Chat/MessageItem.tsx
index 2f7cb0669..86c266f88 100644
--- a/frontend-modern/src/components/AI/Chat/MessageItem.tsx
+++ b/frontend-modern/src/components/AI/Chat/MessageItem.tsx
@@ -37,7 +37,7 @@ interface MessageItemProps {
   onRetry?: (messageId: string) => void;
   onChangeModel?: () => void;
   modelRouteAlternative?: ModelRouteRecoveryOption | null;
-  onUseModelRoute?: (modelId: string) => void;
+  onUseModelRoute?: (modelId: string, messageId?: string) => void;
 }
 
 const markdownClass =
@@ -298,13 +298,15 @@ export const MessageItem: Component<MessageItemProps> = (props) => {
                         {(alternative) => (
                           <button
                             type="button"
-                            onClick={() => props.onUseModelRoute?.(alternative().id)}
-                            aria-label={`Use ${alternative().providerLabel} provider route`}
+                            onClick={() =>
+                              props.onUseModelRoute?.(alternative().id, props.message.id)
+                            }
+                            aria-label={`Retry via ${alternative().providerLabel} provider route`}
                             title={alternative().label}
-                            class="inline-flex max-w-[11rem] items-center gap-1.5 rounded-md border border-red-300 bg-white/80 px-2 py-1 text-xs font-medium text-red-700 transition-colors hover:bg-red-100 dark:border-red-800 dark:bg-red-950/20 dark:text-red-300 dark:hover:bg-red-900/40"
+                            class="inline-flex max-w-[14rem] items-center gap-1.5 rounded-md border border-red-300 bg-white/80 px-2 py-1 text-xs font-medium text-red-700 transition-colors hover:bg-red-100 dark:border-red-800 dark:bg-red-950/20 dark:text-red-300 dark:hover:bg-red-900/40"
                           >
                             <CpuIcon class="h-3.5 w-3.5" />
-                            <span class="truncate">Use {alternative().providerLabel}</span>
+                            <span class="truncate">Retry via {alternative().providerLabel}</span>
                           </button>
                         )}
                       </Show>
diff --git a/frontend-modern/src/components/AI/Chat/__tests__/AIChat.test.tsx b/frontend-modern/src/components/AI/Chat/__tests__/AIChat.test.tsx
index 5599a4ed5..e0a2347cb 100644
--- a/frontend-modern/src/components/AI/Chat/__tests__/AIChat.test.tsx
+++ b/frontend-modern/src/components/AI/Chat/__tests__/AIChat.test.tsx
@@ -21,7 +21,7 @@ const {
     messages: ChatMessage[];
     onChangeModel?: () => void;
     getModelRouteAlternative?: (message: ChatMessage) => ModelRouteRecoveryOption | null;
-    onUseModelRoute?: (modelId: string) => void;
+    onUseModelRoute?: (modelId: string, messageId?: string) => void;
   }> = [];
   const mockChat = {
     messages: vi.fn((): ChatMessage[] => []),
@@ -32,6 +32,7 @@ const {
     queuedFollowUps: vi.fn((): QueuedFollowUp[] => []),
     queuedFollowUpCount: vi.fn(() => 0),
     sendMessage: vi.fn().mockResolvedValue(true),
+    retryMessage: vi.fn(),
     stop: vi.fn(),
     cancelQueuedFollowUp: vi.fn(),
     takeQueuedFollowUp: vi.fn((): QueuedFollowUp | undefined => undefined),
@@ -193,11 +194,12 @@ vi.mock('../ChatMessages', () => ({
     emptyState?: { title: string; subtitle?: string };
     onChangeModel?: () => void;
     getModelRouteAlternative?: (message: ChatMessage) => ModelRouteRecoveryOption | null;
-    onUseModelRoute?: (modelId: string) => void;
+    onUseModelRoute?: (modelId: string, messageId?: string) => void;
   }) => {
-    const routeAlternative = () => {
+    const routeRecovery = () => {
       const failedMessage = props.messages.find((message) => message.error);
-      return failedMessage ? props.getModelRouteAlternative?.(failedMessage) : null;
+      const alternative = failedMessage ? props.getModelRouteAlternative?.(failedMessage) : null;
+      return failedMessage && alternative ? { alternative, failedMessage } : null;
     };
     mockChatMessagesProps.push(props);
     return (
@@ -215,14 +217,16 @@ vi.mock('../ChatMessages', () => ({
         >
           Change model
         </button>
-        <Show when={routeAlternative()}>
-          {(alternative) => (
+        <Show when={routeRecovery()}>
+          {(recovery) => (
             <button
               type="button"
               data-testid="mock-use-model-route"
-              onClick={() => props.onUseModelRoute?.(alternative().id)}
+              onClick={() =>
+                props.onUseModelRoute?.(recovery().alternative.id, recovery().failedMessage.id)
+              }
             >
-              Use {alternative().providerLabel}
+              Retry via {recovery().alternative.providerLabel}
             </button>
           )}
         </Show>
@@ -433,7 +437,7 @@ describe('AIChat', () => {
       });
     });
 
-    it('switches a failed turn to an equivalent configured-provider route', async () => {
+    it('switches a failed turn to an equivalent configured-provider route and retries it', async () => {
       mockChat.model.mockReturnValue('deepseek:deepseek-v4-pro');
       mockChat.messages.mockReturnValue([
         {
@@ -476,6 +480,7 @@ describe('AIChat', () => {
       fireEvent.click(await screen.findByTestId('mock-use-model-route'));
 
       expect(mockChat.setModel).toHaveBeenCalledWith('openrouter:deepseek/deepseek-v4-pro');
+      expect(mockChat.retryMessage).toHaveBeenCalledWith('assistant-error-1');
       expect(document.activeElement).toBe(
         screen.getByPlaceholderText('Ask about your infrastructure...'),
       );
diff --git a/frontend-modern/src/components/AI/Chat/__tests__/ChatMessages.test.tsx b/frontend-modern/src/components/AI/Chat/__tests__/ChatMessages.test.tsx
index 1371996a8..a3e469b44 100644
--- a/frontend-modern/src/components/AI/Chat/__tests__/ChatMessages.test.tsx
+++ b/frontend-modern/src/components/AI/Chat/__tests__/ChatMessages.test.tsx
@@ -20,7 +20,7 @@ let capturedMessageItemProps: Array<{
   onSkipQuestion: (questionId: string) => void;
   onChangeModel?: () => void;
   modelRouteAlternative?: ModelRouteRecoveryOption | null;
-  onUseModelRoute?: (modelId: string) => void;
+  onUseModelRoute?: (modelId: string, messageId?: string) => void;
 }> = [];
 
 vi.mock('../MessageItem', () => ({
@@ -35,7 +35,7 @@ vi.mock('../MessageItem', () => ({
     onSkipQuestion: (questionId: string) => void;
     onChangeModel?: () => void;
     modelRouteAlternative?: ModelRouteRecoveryOption | null;
-    onUseModelRoute?: (modelId: string) => void;
+    onUseModelRoute?: (modelId: string, messageId?: string) => void;
   }) => {
     capturedMessageItemProps.push(props);
     return (
diff --git a/frontend-modern/src/components/AI/Chat/__tests__/MessageItem.test.tsx b/frontend-modern/src/components/AI/Chat/__tests__/MessageItem.test.tsx
index e7b6cf8f1..f87789723 100644
--- a/frontend-modern/src/components/AI/Chat/__tests__/MessageItem.test.tsx
+++ b/frontend-modern/src/components/AI/Chat/__tests__/MessageItem.test.tsx
@@ -172,12 +172,15 @@ describe('MessageItem', () => {
       expect(alert).toBeInTheDocument();
       expect(alert.textContent).toContain('billing or quota reasons');
 
-      const useOpenRouter = screen.getByRole('button', {
-        name: 'Use OpenRouter provider route',
+      const retryViaOpenRouter = screen.getByRole('button', {
+        name: 'Retry via OpenRouter provider route',
       });
-      expect(useOpenRouter).toHaveTextContent('Use OpenRouter');
-      fireEvent.click(useOpenRouter);
-      expect(onUseModelRoute).toHaveBeenCalledWith('openrouter:deepseek/deepseek-v4-pro');
+      expect(retryViaOpenRouter).toHaveTextContent('Retry via OpenRouter');
+      fireEvent.click(retryViaOpenRouter);
+      expect(onUseModelRoute).toHaveBeenCalledWith(
+        'openrouter:deepseek/deepseek-v4-pro',
+        'msg-1',
+      );
 
       const changeModel = screen.getByRole('button', { name: /change model/i });
       fireEvent.click(changeModel);
diff --git a/frontend-modern/src/components/AI/Chat/index.tsx b/frontend-modern/src/components/AI/Chat/index.tsx
index 526139bdc..8cf618190 100644
--- a/frontend-modern/src/components/AI/Chat/index.tsx
+++ b/frontend-modern/src/components/AI/Chat/index.tsx
@@ -900,8 +900,11 @@ export const AIChat: Component<AIChatProps> = (props) => {
     return modelRouteAlternativeFor(message.model || selectedChatModel());
   };
 
-  const switchToModelRoute = (modelId: string) => {
+  const switchToModelRoute = (modelId: string, failedMessageId?: string) => {
     selectModel(modelId);
+    if (failedMessageId) {
+      chat.retryMessage(failedMessageId);
+    }
     focusComposer();
   };