From 1c35ec6cd73ff84e4b65a1435c42438c479041eb Mon Sep 17 00:00:00 2001
From: Shakker <shakkerdroid@gmail.com>
Date: Mon, 25 May 2026 18:23:34 +0100
Subject: [PATCH] fix: preserve chat send user turns on started failures

---
 src/agents/cli-runner.reliability.test.ts     | 12 ++++----
 .../chat.directive-tags.test.ts               | 28 +++++++++++++++++++
 src/gateway/server-methods/chat.ts            |  8 ++++++
 3 files changed, 42 insertions(+), 6 deletions(-)

diff --git a/src/agents/cli-runner.reliability.test.ts b/src/agents/cli-runner.reliability.test.ts
index db33e5eac95f..2cc29ac88990 100644
--- a/src/agents/cli-runner.reliability.test.ts
+++ b/src/agents/cli-runner.reliability.test.ts
@@ -10,6 +10,7 @@ import {
 } from "../auto-reply/reply/reply-run-registry.js";
 import type { OpenClawConfig } from "../config/types.openclaw.js";
 import { getGlobalHookRunner } from "../plugins/hook-runner-global.js";
+import { buildPersistedUserTurnMessage } from "../sessions/user-turn-transcript.js";
 import { runPreparedCliAgent } from "./cli-runner.js";
 import {
   createManagedRun,
@@ -900,12 +901,11 @@ describe("runCliAgent reliability", () => {
           workspaceDir: dir,
           prompt: "runtime image prompt",
           userTurnTranscript: {
-            message: {
-              role: "user",
-              content: "describe this",
-              MediaPath: "/tmp/image.png",
-              MediaType: "image/png",
-            },
+            message: buildPersistedUserTurnMessage({
+              text: "describe this",
+              media: [{ path: "/tmp/image.png", contentType: "image/png" }],
+              timestamp: 123,
+            }),
           },
           onUserMessagePersisted,
         },
diff --git a/src/gateway/server-methods/chat.directive-tags.test.ts b/src/gateway/server-methods/chat.directive-tags.test.ts
index bc5e184e0e42..60168908fccc 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -4422,6 +4422,34 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
       expect(persistedUser?.content).toBe("hello before cli startup failure");
     });
   });
+
+  it("emits a user transcript update when a started agent returns an error before runtime persistence", async () => {
+    createTranscriptFixture("openclaw-chat-send-user-transcript-agent-error-no-runtime-persist-");
+    mockState.triggerAgentRunStart = true;
+    mockState.finalPayload = { text: "agent failed before prompt append", isError: true };
+    const respond = vi.fn();
+    const context = createChatContext();
+
+    await runNonStreamingChatSend({
+      context,
+      respond,
+      idempotencyKey: "idem-user-transcript-agent-error-no-runtime-persist",
+      message: "hello before agent error payload",
+      expectBroadcast: false,
+    });
+
+    await waitForAssertion(() => {
+      expect(
+        context.dedupe.get("chat:idem-user-transcript-agent-error-no-runtime-persist")?.ok,
+      ).toBe(false);
+      const userUpdate = findUserUpdate();
+      const message = userUpdateMessage(userUpdate);
+      expect(userUpdate?.sessionFile.endsWith("sess.jsonl")).toBe(true);
+      expect(userUpdate?.sessionKey).toBe("main");
+      expect(message?.role).toBe("user");
+      expect(message?.content).toBe("hello before agent error payload");
+    });
+  });
 });
 
 describe("chat.send operator UI client sender context", () => {
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 9d1566feff44..e5de986bbb0a 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -2910,6 +2910,14 @@ export const chatHandlers: GatewayRequestHandlers = {
                   .map((payload) => payload.text?.trim())
                   .filter((text): text is string => Boolean(text))
                   .join(" | ") || undefined;
+              if (
+                agentRunStarted &&
+                returnedAgentErrorPayloads.length > 0 &&
+                !agentUserMessagePersisted &&
+                !beforeAgentRunHooksRegistered
+              ) {
+                await persistGatewayUserTurnTranscript();
+              }
               let broadcastedSourceReplyFinal = false;
               // WebChat persistence has two owners. Agent runs persist model-visible turns
               // through Pi's SessionManager; this dispatcher only owns live delivery payloads.