diff --git a/CHANGELOG.md b/CHANGELOG.md
index 291feb3fa..7847e2cf5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -78,6 +78,7 @@
 - Fix: normalize pairing CLI aliases, allow extension channels, and harden Zalo webhook payload parsing. (#991) — thanks @longmaba.
 - Fix: allow local Tailscale Serve hostnames without treating tailnet clients as direct. (#885) — thanks @oswalpalash.
 - Fix: reset sessions after role-ordering conflicts to recover from consecutive user turns. (#998)
+- Fix: repair orphaned user turns before embedded prompts to avoid role-ordering lockouts. (#1026) — thanks @odrobnik.
 - Fix: keep background exec aborts from killing backgrounded sessions while honoring timeouts.
 - Fix: use local auth for gateway security probe unless remote mode has a URL. (#1011) — thanks @ivanrvpereira.
 - Discord: truncate skill command descriptions for slash command limits. (#1018) — thanks @evalexpr.
diff --git a/src/agents/pi-embedded-runner.run-embedded-pi-agent.appends-new-user-assistant-after-existing-transcript.test.ts b/src/agents/pi-embedded-runner.run-embedded-pi-agent.appends-new-user-assistant-after-existing-transcript.test.ts
index 5c2df46dd..68bf5a7da 100644
--- a/src/agents/pi-embedded-runner.run-embedded-pi-agent.appends-new-user-assistant-after-existing-transcript.test.ts
+++ b/src/agents/pi-embedded-runner.run-embedded-pi-agent.appends-new-user-assistant-after-existing-transcript.test.ts
@@ -261,7 +261,7 @@ describe("runEmbeddedPiAgent", () => {
     expect(secondUserIndex).toBeGreaterThan(firstAssistantIndex);
     expect(secondAssistantIndex).toBeGreaterThan(secondUserIndex);
   }, 20_000);
-  it("returns role ordering error when session ends with a user turn", async () => {
+  it("repairs orphaned user messages and continues", async () => {
     const { SessionManager } = await import("@mariozechner/pi-coding-agent");
 
     const agentDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-agent-"));
@@ -317,8 +317,40 @@ describe("runEmbeddedPiAgent", () => {
       agentDir,
     });
 
-    expect(result.meta.error?.kind).toBe("role_ordering");
-    expect(result.meta.error?.message).toMatch(/incorrect role information|roles must alternate/i);
-    expect(result.payloads?.[0]?.text).toContain("Message ordering conflict");
+    expect(result.meta.error).toBeUndefined();
+    expect(result.payloads?.length ?? 0).toBeGreaterThan(0);
+  });
+
+  it("repairs orphaned single-user sessions and continues", async () => {
+    const { SessionManager } = await import("@mariozechner/pi-coding-agent");
+
+    const agentDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-agent-"));
+    const workspaceDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-workspace-"));
+    const sessionFile = path.join(workspaceDir, "session.jsonl");
+
+    const sessionManager = SessionManager.open(sessionFile);
+    sessionManager.appendMessage({
+      role: "user",
+      content: [{ type: "text", text: "seed user only" }],
+    });
+
+    const cfg = makeOpenAiConfig(["mock-1"]);
+    await ensureModels(cfg, agentDir);
+
+    const result = await runEmbeddedPiAgent({
+      sessionId: "session:test",
+      sessionKey: "agent:main:main",
+      sessionFile,
+      workspaceDir,
+      config: cfg,
+      prompt: "hello",
+      provider: "openai",
+      model: "mock-1",
+      timeoutMs: 5_000,
+      agentDir,
+    });
+
+    expect(result.meta.error).toBeUndefined();
+    expect(result.payloads?.length ?? 0).toBeGreaterThan(0);
   });
 });
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index b58ceeea4..2ca91ac7b 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -441,35 +441,30 @@ export async function runEmbeddedAttempt(
         const promptStartedAt = Date.now();
         log.debug(`embedded run prompt start: runId=${params.runId} sessionId=${params.sessionId}`);
 
-        // Check if last message is a user message to prevent consecutive user turns
-        const lastMsg = activeSession.messages[activeSession.messages.length - 1];
-        const lastMsgRole =
-          lastMsg && typeof lastMsg === "object" ? (lastMsg as { role?: unknown }).role : undefined;
-
-        if (lastMsgRole === "user") {
-          // Last message was a user message. Adding another user message would create
-          // consecutive user turns, violating Anthropic's role ordering requirement.
-          // This can happen when:
-          // 1. A previous heartbeat didn't get a response
-          // 2. A user message errored before getting an assistant response
-          // Skip this prompt to prevent "400 Incorrect role information" error.
+        // Repair orphaned trailing user messages so new prompts don't violate role ordering.
+        const leafEntry = sessionManager.getLeafEntry();
+        if (leafEntry?.type === "message" && leafEntry.message.role === "user") {
+          if (leafEntry.parentId) {
+            sessionManager.branch(leafEntry.parentId);
+          } else {
+            sessionManager.resetLeaf();
+          }
+          const sessionContext = sessionManager.buildSessionContext();
+          activeSession.agent.replaceMessages(sessionContext.messages);
           log.warn(
-            `Skipping prompt because last message is a user message (would create consecutive user turns). ` +
+            `Removed orphaned user message to prevent consecutive user turns. ` +
               `runId=${params.runId} sessionId=${params.sessionId}`,
           );
-          promptError = new Error(
-            "Incorrect role information: consecutive user messages would violate role ordering",
+        }
+
+        try {
+          await activeSession.prompt(params.prompt, { images: params.images });
+        } catch (err) {
+          promptError = err;
+        } finally {
+          log.debug(
+            `embedded run prompt end: runId=${params.runId} sessionId=${params.sessionId} durationMs=${Date.now() - promptStartedAt}`,
           );
-        } else {
-          try {
-            await activeSession.prompt(params.prompt, { images: params.images });
-          } catch (err) {
-            promptError = err;
-          } finally {
-            log.debug(
-              `embedded run prompt end: runId=${params.runId} sessionId=${params.sessionId} durationMs=${Date.now() - promptStartedAt}`,
-            );
-          }
         }
 
         try {