diff --git a/ui/src/pages/chat/chat-send-actions.ts b/ui/src/pages/chat/chat-send-actions.ts
index 01754a8af33d..14239c7c6241 100644
--- a/ui/src/pages/chat/chat-send-actions.ts
+++ b/ui/src/pages/chat/chat-send-actions.ts
@@ -168,7 +168,7 @@ export function moveQueuedChatMessage(host: ChatHost, id: string, toIndex: numbe
 }
 
 export async function retryQueuedChatMessage(host: ChatHost, id: string) {
-  const item = host.chatQueue.find((entry) => entry.id === id);
+  let item = host.chatQueue.find((entry) => entry.id === id);
   if (
     !item ||
     item.pendingRunId ||
@@ -180,23 +180,39 @@ export async function retryQueuedChatMessage(host: ChatHost, id: string) {
     return;
   }
   if (item.kind === "steered") {
-    if (!host.connected || !host.client || !hasAbortableSessionRun(host)) {
+    if (!host.connected || !host.client) {
       setChatError(host, t("chat.sendErrors.steerRunNoLongerActive"));
       return;
     }
-    const retry = updateQueuedMessage(host, id, (entry) => ({
-      ...entry,
-      sendAttempts: 0,
-      sendError: undefined,
-      sendRequestStartedAtMs: undefined,
-      sendState: "waiting-idle",
-    }));
-    if (!retry) {
+    if (hasAbortableSessionRun(host)) {
+      const retry = updateQueuedMessage(host, id, (entry) => ({
+        ...entry,
+        sendAttempts: 0,
+        sendError: undefined,
+        sendRequestStartedAtMs: undefined,
+        sendState: "waiting-idle",
+      }));
+      if (!retry) {
+        setChatError(host, OFFLINE_QUEUE_STORAGE_ERROR);
+        return;
+      }
+      await steerQueuedChatMessageLifecycle(host, id, steerSendDependencies);
+      return;
+    }
+    const converted = updateQueuedMessage(host, id, (entry) => {
+      const {
+        kind: _kind,
+        pendingRunId: _pendingRunId,
+        steerTargetRunId: _steerTargetRunId,
+        ...queued
+      } = entry;
+      return resetRetryState(queued, reconnectSafeQueuedSendState(host));
+    });
+    if (!converted) {
       setChatError(host, OFFLINE_QUEUE_STORAGE_ERROR);
       return;
     }
-    await steerQueuedChatMessageLifecycle(host, id, steerSendDependencies);
-    return;
+    item = converted;
   }
   let outbox = findStoredOutbox(host, item.id);
   if (!outbox) {
diff --git a/ui/src/pages/chat/chat-send.test.ts b/ui/src/pages/chat/chat-send.test.ts
index c60823c8d2ea..42b6ef5ee132 100644
--- a/ui/src/pages/chat/chat-send.test.ts
+++ b/ui/src/pages/chat/chat-send.test.ts
@@ -8797,13 +8797,14 @@ describe("handleSendChat", () => {
     ]);
     expect(host.lastError).toBe("no active turn to steer");
 
-    host.chatRunId = null;
+    host.connected = false;
     await retryQueuedChatMessage(host, original.id);
     expect(payloads).toHaveLength(1);
     expect(host.lastError).toBe(
       "This steer still targets the previous run, but that run is no longer active.",
     );
 
+    host.connected = true;
     host.chatRunId = "active-run";
     host.chatDisplayedLeafEntryId = "leaf-advanced-during-tool-work";
     await retryQueuedChatMessage(host, original.id);
@@ -8821,6 +8822,49 @@ describe("handleSendChat", () => {
     ]);
   });
 
+  it("retries a failed steer as a new turn when the session is idle", async () => {
+    const payloads: Array<Record<string, unknown>> = [];
+    const original = {
+      id: "idle-failed-steer",
+      text: "deliver this as a new turn",
+      createdAt: 1,
+      kind: "steered" as const,
+      sendAttempts: 1,
+      sendError: "The session switched branches — review and resend.",
+      sendRequestStartedAtMs: 123,
+      sendRunId: "previous-steer-request",
+      sendState: "failed" as const,
+      steerTargetRunId: "previous-run",
+      sessionKey: "agent:main:main",
+      agentId: "main",
+    };
+    const host = makeChatHost({
+      requestHandlers: {
+        "chat.history": idleChatHistory(original.sessionKey),
+        "chat.send": (params: unknown) => {
+          payloads.push(requireRecord(params, "idle steer retry payload"));
+          return { status: "ok", runId: "new-turn" };
+        },
+      },
+      chatError: "The session switched branches — review and resend.",
+      chatQueue: [original],
+      sessionKey: original.sessionKey,
+    });
+    expect(admitQueuedMessageForSession(host, host.sessionKey, original)).toBe(true);
+
+    await retryQueuedChatMessage(host, original.id);
+
+    expect(payloads).toHaveLength(1);
+    expect(payloads[0]).toMatchObject({ message: original.text });
+    expect(payloads[0]).not.toHaveProperty("expectedRunId");
+    expect(payloads[0]).not.toHaveProperty("expectedLeafEntryId");
+    expect(payloads[0]).not.toHaveProperty("queueMode");
+    expect(payloads[0]?.idempotencyKey).not.toBe(original.sendRunId);
+    expect(host.chatQueue).toEqual([]);
+    expect(host.chatError).toBeNull();
+    expect(host.lastError).toBeNull();
+  });
+
   it("fails a restored steer that predates durable target identity", async () => {
     const original = {
       id: "legacy-targetless-steer",