diff --git a/CHANGELOG.md b/CHANGELOG.md
index 57a5b003f..1ab9a4f9a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -51,6 +51,7 @@
 - Fix: sanitize user-facing error text + strip `<final>` tags across reply pipelines. (#975) — thanks @ThomsenDrake.
 - 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)
 
 ## 2026.1.14-1
 
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 d559ce62e..5c2df46dd 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
@@ -261,4 +261,64 @@ 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 () => {
+    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 1" }],
+    });
+    sessionManager.appendMessage({
+      role: "assistant",
+      content: [{ type: "text", text: "seed assistant" }],
+      stopReason: "stop",
+      api: "openai-responses",
+      provider: "openai",
+      model: "mock-1",
+      usage: {
+        input: 1,
+        output: 1,
+        cacheRead: 0,
+        cacheWrite: 0,
+        totalTokens: 2,
+        cost: {
+          input: 0,
+          output: 0,
+          cacheRead: 0,
+          cacheWrite: 0,
+          total: 0,
+        },
+      },
+      timestamp: Date.now(),
+    });
+    sessionManager.appendMessage({
+      role: "user",
+      content: [{ type: "text", text: "seed user 2" }],
+    });
+
+    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?.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");
+  });
 });
diff --git a/src/agents/pi-embedded-runner/run.ts b/src/agents/pi-embedded-runner/run.ts
index f05703c95..757c429fa 100644
--- a/src/agents/pi-embedded-runner/run.ts
+++ b/src/agents/pi-embedded-runner/run.ts
@@ -274,6 +274,8 @@ export async function runEmbeddedPiAgent(
                     provider,
                     model: model.id,
                   },
+                  systemPromptReport: attempt.systemPromptReport,
+                  error: { kind: "role_ordering", message: errorText },
                 },
               };
             }
diff --git a/src/agents/pi-embedded-runner/types.ts b/src/agents/pi-embedded-runner/types.ts
index 3525de004..e2d33047a 100644
--- a/src/agents/pi-embedded-runner/types.ts
+++ b/src/agents/pi-embedded-runner/types.ts
@@ -20,7 +20,7 @@ export type EmbeddedPiRunMeta = {
   aborted?: boolean;
   systemPromptReport?: SessionSystemPromptReport;
   error?: {
-    kind: "context_overflow" | "compaction_failure";
+    kind: "context_overflow" | "compaction_failure" | "role_ordering";
     message: string;
   };
 };
diff --git a/src/auto-reply/reply/agent-runner-execution.ts b/src/auto-reply/reply/agent-runner-execution.ts
index abecf58be..ba6665860 100644
--- a/src/auto-reply/reply/agent-runner-execution.ts
+++ b/src/auto-reply/reply/agent-runner-execution.ts
@@ -63,6 +63,7 @@ export async function runAgentTurnWithFallback(params: {
   shouldEmitToolResult: () => boolean;
   pendingToolTasks: Set<Promise<void>>;
   resetSessionAfterCompactionFailure: (reason: string) => Promise<boolean>;
+  resetSessionAfterRoleOrderingConflict: (reason: string) => Promise<boolean>;
   isHeartbeat: boolean;
   sessionKey?: string;
   getActiveSessionEntry: () => SessionEntry | undefined;
@@ -376,6 +377,17 @@ export async function runAgentTurnWithFallback(params: {
         didResetAfterCompactionFailure = true;
         continue;
       }
+      if (embeddedError?.kind === "role_ordering") {
+        const didReset = await params.resetSessionAfterRoleOrderingConflict(embeddedError.message);
+        if (didReset) {
+          return {
+            kind: "final",
+            payload: {
+              text: "⚠️ Message ordering conflict. I've reset the conversation - please try again.",
+            },
+          };
+        }
+      }
 
       break;
     } catch (err) {
@@ -395,6 +407,17 @@ export async function runAgentTurnWithFallback(params: {
         didResetAfterCompactionFailure = true;
         continue;
       }
+      if (isRoleOrderingError) {
+        const didReset = await params.resetSessionAfterRoleOrderingConflict(message);
+        if (didReset) {
+          return {
+            kind: "final",
+            payload: {
+              text: "⚠️ Message ordering conflict. I've reset the conversation - please try again.",
+            },
+          };
+        }
+      }
 
       // Auto-recover from Gemini session corruption by resetting the session
       if (
diff --git a/src/auto-reply/reply/agent-runner.heartbeat-typing.runreplyagent-typing-heartbeat.retries-after-compaction-failure-by-resetting-session.test.ts b/src/auto-reply/reply/agent-runner.heartbeat-typing.runreplyagent-typing-heartbeat.retries-after-compaction-failure-by-resetting-session.test.ts
index cc490f6d1..6978f88fc 100644
--- a/src/auto-reply/reply/agent-runner.heartbeat-typing.runreplyagent-typing-heartbeat.retries-after-compaction-failure-by-resetting-session.test.ts
+++ b/src/auto-reply/reply/agent-runner.heartbeat-typing.runreplyagent-typing-heartbeat.retries-after-compaction-failure-by-resetting-session.test.ts
@@ -212,6 +212,55 @@ describe("runReplyAgent typing (heartbeat)", () => {
       expect(payload).toMatchObject({ text: "ok" });
       expect(sessionStore.main.sessionId).not.toBe(sessionId);
 
+      const persisted = JSON.parse(await fs.readFile(storePath, "utf-8"));
+      expect(persisted.main.sessionId).toBe(sessionStore.main.sessionId);
+    } finally {
+      if (prevStateDir) {
+        process.env.CLAWDBOT_STATE_DIR = prevStateDir;
+      } else {
+        delete process.env.CLAWDBOT_STATE_DIR;
+      }
+    }
+  });
+  it("resets the session after role ordering payloads", async () => {
+    const prevStateDir = process.env.CLAWDBOT_STATE_DIR;
+    const stateDir = await fs.mkdtemp(path.join(tmpdir(), "clawdbot-session-role-ordering-"));
+    process.env.CLAWDBOT_STATE_DIR = stateDir;
+    try {
+      const sessionId = "session";
+      const storePath = path.join(stateDir, "sessions", "sessions.json");
+      const sessionEntry = { sessionId, updatedAt: Date.now() };
+      const sessionStore = { main: sessionEntry };
+
+      await fs.mkdir(path.dirname(storePath), { recursive: true });
+      await fs.writeFile(storePath, JSON.stringify(sessionStore), "utf-8");
+
+      runEmbeddedPiAgentMock.mockImplementationOnce(async () => ({
+        payloads: [{ text: "Message ordering conflict - please try again.", isError: true }],
+        meta: {
+          durationMs: 1,
+          error: {
+            kind: "role_ordering",
+            message: 'messages: roles must alternate between "user" and "assistant"',
+          },
+        },
+      }));
+
+      const { run } = createMinimalRun({
+        sessionEntry,
+        sessionStore,
+        sessionKey: "main",
+        storePath,
+      });
+      const res = await run();
+
+      const payload = Array.isArray(res) ? res[0] : res;
+      expect(payload).toMatchObject({
+        text: expect.stringContaining("Message ordering conflict"),
+      });
+      expect(payload.text?.toLowerCase()).toContain("reset");
+      expect(sessionStore.main.sessionId).not.toBe(sessionId);
+
       const persisted = JSON.parse(await fs.readFile(storePath, "utf-8"));
       expect(persisted.main.sessionId).toBe(sessionStore.main.sessionId);
     } finally {
diff --git a/src/auto-reply/reply/agent-runner.ts b/src/auto-reply/reply/agent-runner.ts
index c23328f58..215756967 100644
--- a/src/auto-reply/reply/agent-runner.ts
+++ b/src/auto-reply/reply/agent-runner.ts
@@ -245,6 +245,42 @@ export async function runReplyAgent(params: {
     );
     return true;
   };
+  const resetSessionAfterRoleOrderingConflict = async (reason: string): Promise<boolean> => {
+    if (!sessionKey || !activeSessionStore || !storePath) return false;
+    const nextSessionId = crypto.randomUUID();
+    const nextEntry: SessionEntry = {
+      ...(activeSessionStore[sessionKey] ?? activeSessionEntry),
+      sessionId: nextSessionId,
+      updatedAt: Date.now(),
+      systemSent: false,
+      abortedLastRun: false,
+    };
+    const agentId = resolveAgentIdFromSessionKey(sessionKey);
+    const nextSessionFile = resolveSessionTranscriptPath(
+      nextSessionId,
+      agentId,
+      sessionCtx.MessageThreadId,
+    );
+    nextEntry.sessionFile = nextSessionFile;
+    activeSessionStore[sessionKey] = nextEntry;
+    try {
+      await updateSessionStore(storePath, (store) => {
+        store[sessionKey] = nextEntry;
+      });
+    } catch (err) {
+      defaultRuntime.error(
+        `Failed to persist session reset after role ordering conflict (${sessionKey}): ${String(err)}`,
+      );
+    }
+    followupRun.run.sessionId = nextSessionId;
+    followupRun.run.sessionFile = nextSessionFile;
+    activeSessionEntry = nextEntry;
+    activeIsNewSession = true;
+    defaultRuntime.error(
+      `Role ordering conflict (${reason}). Restarting session ${sessionKey} -> ${nextSessionId}.`,
+    );
+    return true;
+  };
   try {
     const runOutcome = await runAgentTurnWithFallback({
       commandBody,
@@ -260,6 +296,7 @@ export async function runReplyAgent(params: {
       shouldEmitToolResult,
       pendingToolTasks,
       resetSessionAfterCompactionFailure,
+      resetSessionAfterRoleOrderingConflict,
       isHeartbeat,
       sessionKey,
       getActiveSessionEntry: () => activeSessionEntry,