diff --git a/packages/server/src/server/agent/providers/claude-agent.ts b/packages/server/src/server/agent/providers/claude-agent.ts
index ee614fb7f..f2b26c3a2 100644
--- a/packages/server/src/server/agent/providers/claude-agent.ts
+++ b/packages/server/src/server/agent/providers/claude-agent.ts
@@ -1087,11 +1087,6 @@ class ClaudeAgentSession implements AgentSession {
     invocation: SlashCommandInvocation
   ): AsyncGenerator<AgentStreamEvent> {
     yield { type: "turn_started", provider: "claude" };
-    yield {
-      type: "timeline",
-      provider: "claude",
-      item: { type: "user_message", text: invocation.rawInput },
-    };
 
     try {
       const rewindAttempt = await this.attemptRewind(invocation.args);
diff --git a/packages/server/src/server/daemon-e2e/rewind-user-message-dedupe-claude.real.e2e.test.ts b/packages/server/src/server/daemon-e2e/rewind-user-message-dedupe-claude.real.e2e.test.ts
new file mode 100644
index 000000000..3e784bcf4
--- /dev/null
+++ b/packages/server/src/server/daemon-e2e/rewind-user-message-dedupe-claude.real.e2e.test.ts
@@ -0,0 +1,73 @@
+import { describe, expect, test } from "vitest";
+import { mkdtempSync, rmSync } from "node:fs";
+import { tmpdir } from "node:os";
+import path from "node:path";
+import pino from "pino";
+
+import { createTestPaseoDaemon } from "../test-utils/paseo-daemon.js";
+import { DaemonClient } from "../test-utils/daemon-client.js";
+import { ClaudeAgentClient } from "../agent/providers/claude-agent.js";
+import { getFullAccessConfig } from "./agent-configs.js";
+import { isCommandAvailable } from "../agent/provider-launch-config.js";
+
+function tmpCwd(): string {
+  return mkdtempSync(path.join(tmpdir(), "daemon-rewind-dedupe-real-claude-"));
+}
+
+const hasClaudeCredentials =
+  !!process.env.CLAUDE_CODE_OAUTH_TOKEN || !!process.env.ANTHROPIC_API_KEY;
+
+describe("daemon E2E (real claude) - rewind user message dedupe", () => {
+  test.runIf(isCommandAvailable("claude") && hasClaudeCredentials)(
+    "emits /rewind user message once in persisted timeline",
+    async () => {
+      const logger = pino({ level: "silent" });
+      const cwd = tmpCwd();
+      const daemon = await createTestPaseoDaemon({
+        agentClients: { claude: new ClaudeAgentClient({ logger }) },
+        logger,
+      });
+      const client = new DaemonClient({ url: `ws://127.0.0.1:${daemon.port}/ws` });
+
+      try {
+        await client.connect();
+        await client.fetchAgents({
+          subscribe: { subscriptionId: "rewind-user-message-dedupe" },
+        });
+
+        const agent = await client.createAgent({
+          cwd,
+          title: "rewind-user-message-dedupe-real-claude",
+          ...getFullAccessConfig("claude"),
+        });
+
+        await client.sendMessage(agent.id, "Reply with exactly: READY");
+        const initialResult = await client.waitForFinish(agent.id, 180_000);
+        expect(initialResult.status).toBe("idle");
+
+        await client.sendMessage(agent.id, "/rewind");
+        const rewindResult = await client.waitForFinish(agent.id, 180_000);
+        expect(rewindResult.status).not.toBe("timeout");
+
+        const timeline = await client.fetchAgentTimeline(agent.id, {
+          direction: "tail",
+          limit: 0,
+          projection: "canonical",
+        });
+
+        const rewindUserMessages = timeline.entries.filter(
+          (entry) =>
+            entry.item.type === "user_message" &&
+            entry.item.text.trim() === "/rewind"
+        );
+
+        expect(rewindUserMessages).toHaveLength(1);
+      } finally {
+        await client.close();
+        await daemon.close();
+        rmSync(cwd, { recursive: true, force: true });
+      }
+    },
+    300_000
+  );
+});