diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8b8da00be2a..1cb795f8468 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -87,6 +87,7 @@ Docs: https://docs.openclaw.ai
 - MCP/plugin tools: apply global `tools.profile`, `tools.alsoAllow`, and `tools.deny` policy while exposing plugin tools over the standalone MCP bridge, so ACP clients do not see policy-hidden plugin tools or miss opt-in optional tools. Thanks @vincentkoc.
 - Plugin tools: honor explicit tool denylists while selecting plugin tool runtimes, so denied plugin tools are not materialized for direct command or gateway surfaces before later policy filtering. Thanks @vincentkoc.
 - Plugin tools: filter factory-returned tools by manifest per-tool optional policy, so optional sibling tools from a shared runtime factory stay hidden unless explicitly allowed. Thanks @vincentkoc.
+- Agents/transcripts: retry context-overflow compaction from the current transcript only after the inbound user turn was actually persisted, and keep WebChat agent-run live delivery from writing duplicate Pi-managed assistant turns. Fixes #76424.
 - Agents/bootstrap: keep pending `BOOTSTRAP.md` and bootstrap truncation notices in system-prompt Project Context instead of copying setup text or raw warning diagnostics into WebChat user/runtime context. Fixes #76946.
 - Channels/WhatsApp: allow `@whiskeysockets/libsignal-node` in `onlyBuiltDependencies` so pnpm v9+ `blockExoticSubdeps` no longer rejects the baileys git-tarball subdep and silences all inbound agent replies. Fixes #76539. Thanks @ottodeng and @vincentkoc.
 - Gateway/install: keep `.env`-managed values in the macOS LaunchAgent env file while still tracking `OPENCLAW_SERVICE_MANAGED_ENV_KEYS`, so regenerated services do not boot without managed auth/provider keys. Fixes #75374.
diff --git a/src/agents/pi-embedded-runner/run.overflow-compaction.loop.test.ts b/src/agents/pi-embedded-runner/run.overflow-compaction.loop.test.ts
index c70bedde48e..23b09368d78 100644
--- a/src/agents/pi-embedded-runner/run.overflow-compaction.loop.test.ts
+++ b/src/agents/pi-embedded-runner/run.overflow-compaction.loop.test.ts
@@ -98,6 +98,89 @@ describe("overflow compaction in run loop", () => {
     expect(result.meta.error).toBeUndefined();
   });
 
+  it("continues from transcript after compaction when the current inbound message was persisted", async () => {
+    const overflowError = makeOverflowError();
+
+    mockedRunEmbeddedAttempt
+      .mockImplementationOnce(async (attemptParams) => {
+        (
+          attemptParams as {
+            onUserMessagePersisted?: (message: { role: "user"; content: string }) => void;
+          }
+        ).onUserMessagePersisted?.({ role: "user", content: baseParams.prompt });
+        return makeAttemptResult({ promptError: overflowError });
+      })
+      .mockResolvedValueOnce(makeAttemptResult({ promptError: null }));
+
+    mockedCompactDirect.mockResolvedValueOnce(
+      makeCompactionSuccess({
+        summary: "Compacted session",
+        firstKeptEntryId: "entry-5",
+        tokensBefore: 150000,
+      }),
+    );
+
+    const result = await runEmbeddedPiAgent({
+      ...baseParams,
+      currentMessageId: "telegram-msg-51024",
+    });
+
+    expect(mockedCompactDirect).toHaveBeenCalledTimes(1);
+    expect(mockedRunEmbeddedAttempt).toHaveBeenCalledTimes(2);
+    expect(mockedRunEmbeddedAttempt).toHaveBeenNthCalledWith(
+      2,
+      expect.objectContaining({
+        prompt: expect.stringContaining("Continue from the current transcript"),
+        suppressNextUserMessagePersistence: true,
+      }),
+    );
+    expect(mockedRunEmbeddedAttempt).not.toHaveBeenNthCalledWith(
+      2,
+      expect.objectContaining({ prompt: baseParams.prompt }),
+    );
+    expect(result.meta.error).toBeUndefined();
+  });
+
+  it("does not suppress the next user turn when precheck overflow never persisted it", async () => {
+    const overflowError = makeOverflowError(
+      "Context overflow: prompt too large for the model (precheck).",
+    );
+
+    mockedRunEmbeddedAttempt
+      .mockResolvedValueOnce(
+        makeAttemptResult({
+          promptError: overflowError,
+          promptErrorSource: "precheck",
+          preflightRecovery: { route: "compact_only" },
+        }),
+      )
+      .mockResolvedValueOnce(makeAttemptResult({ promptError: null }));
+
+    mockedCompactDirect.mockResolvedValueOnce(
+      makeCompactionSuccess({
+        summary: "Compacted before prompt submission",
+        firstKeptEntryId: "entry-5",
+        tokensBefore: 150000,
+      }),
+    );
+
+    const result = await runEmbeddedPiAgent({
+      ...baseParams,
+      currentMessageId: "telegram-msg-51025",
+    });
+
+    expect(mockedCompactDirect).toHaveBeenCalledTimes(1);
+    expect(mockedRunEmbeddedAttempt).toHaveBeenCalledTimes(2);
+    expect(mockedRunEmbeddedAttempt).toHaveBeenNthCalledWith(
+      2,
+      expect.objectContaining({
+        prompt: baseParams.prompt,
+        suppressNextUserMessagePersistence: false,
+      }),
+    );
+    expect(result.meta.error).toBeUndefined();
+  });
+
   it("retries after successful compaction on likely-overflow promptError variants", async () => {
     const overflowHintError = new Error("Context window exceeded: requested 12000 tokens");
 
diff --git a/src/agents/pi-embedded-runner/run.ts b/src/agents/pi-embedded-runner/run.ts
index 91d02918cc1..8ea0f8d25f1 100644
--- a/src/agents/pi-embedded-runner/run.ts
+++ b/src/agents/pi-embedded-runner/run.ts
@@ -805,6 +805,16 @@ export async function runEmbeddedPiAgent(
       const rateLimitProfileRotationLimit = resolveRateLimitProfileRotationLimit(params.config);
       let activeSessionId = params.sessionId;
       let activeSessionFile = params.sessionFile;
+      let suppressNextUserMessagePersistence = params.suppressNextUserMessagePersistence ?? false;
+      let lastPersistedCurrentMessageId: string | number | undefined;
+      const onUserMessagePersisted: RunEmbeddedPiAgentParams["onUserMessagePersisted"] = (
+        message,
+      ) => {
+        if (params.currentMessageId !== undefined) {
+          lastPersistedCurrentMessageId = params.currentMessageId;
+        }
+        params.onUserMessagePersisted?.(message);
+      };
       const maybeEscalateRateLimitProfileFallback = (params: {
         failoverProvider: string;
         failoverModel: string;
@@ -1170,8 +1180,8 @@ export async function runEmbeddedPiAgent(
             bootstrapPromptWarningSignaturesSeen,
             bootstrapPromptWarningSignature:
               bootstrapPromptWarningSignaturesSeen[bootstrapPromptWarningSignaturesSeen.length - 1],
-            suppressNextUserMessagePersistence: params.suppressNextUserMessagePersistence,
-            onUserMessagePersisted: params.onUserMessagePersisted,
+            suppressNextUserMessagePersistence,
+            onUserMessagePersisted,
           });
           const attempt = normalizeEmbeddedRunAttemptResult(rawAttempt);
 
@@ -1634,6 +1644,12 @@ export async function runEmbeddedPiAgent(
                 log.info(`auto-compaction succeeded for ${provider}/${modelId}; retrying prompt`);
                 if (preflightRecovery?.source === "mid-turn") {
                   nextAttemptPromptOverride = MID_TURN_PRECHECK_CONTINUATION_PROMPT;
+                } else if (
+                  params.currentMessageId !== undefined &&
+                  params.currentMessageId === lastPersistedCurrentMessageId
+                ) {
+                  nextAttemptPromptOverride = MID_TURN_PRECHECK_CONTINUATION_PROMPT;
+                  suppressNextUserMessagePersistence = true;
                 }
                 continue;
               }
diff --git a/src/gateway/server-methods/chat.directive-tags.test.ts b/src/gateway/server-methods/chat.directive-tags.test.ts
index fe26ee538f2..f68b4316e60 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -716,7 +716,7 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
     );
   });
 
-  it("does not persist agent media supplements when no playable media resolves", async () => {
+  it("does not mirror agent-run stale media final text from live delivery", async () => {
     const transcriptDir = createTranscriptFixture("openclaw-chat-send-agent-stale-tts-");
     const staleAudioPath = path.join(transcriptDir, "stale.mp3");
     mockState.config = {
@@ -756,6 +756,66 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
         (update.message as { role?: unknown }).role === "assistant",
     );
     expect(assistantUpdates).toEqual([]);
+    const transcriptLines = fs
+      .readFileSync(mockState.transcriptPath, "utf-8")
+      .split("\n")
+      .filter(Boolean)
+      .map((line) => JSON.parse(line) as Record<string, unknown>);
+    const assistantEntries = transcriptLines.filter(
+      (entry) =>
+        (entry as { message?: { role?: string } }).message?.role === "assistant" ||
+        (entry as { role?: string }).role === "assistant",
+    );
+    expect(assistantEntries).toEqual([]);
+  });
+
+  it("does not mirror normal agent-run final text from live delivery", async () => {
+    const transcriptDir = createTranscriptFixture("openclaw-chat-send-agent-text-only-");
+    mockState.config = {
+      agents: {
+        defaults: {
+          workspace: transcriptDir,
+        },
+      },
+    };
+    mockState.triggerAgentRunStart = true;
+    mockState.dispatchedReplies = [
+      {
+        kind: "final",
+        payload: {
+          text: "It's 11:52 AM EDT.",
+        },
+      },
+    ];
+    const respond = vi.fn();
+    const context = createChatContext();
+
+    await runNonStreamingChatSend({
+      context,
+      respond,
+      idempotencyKey: "idem-agent-text-only",
+      expectBroadcast: false,
+      waitFor: "dedupe",
+    });
+
+    const assistantUpdates = mockState.emittedTranscriptUpdates.filter(
+      (update) =>
+        typeof update.message === "object" &&
+        update.message !== null &&
+        (update.message as { role?: unknown }).role === "assistant",
+    );
+    expect(assistantUpdates).toEqual([]);
+    const transcriptLines = fs
+      .readFileSync(mockState.transcriptPath, "utf-8")
+      .split("\n")
+      .filter(Boolean)
+      .map((line) => JSON.parse(line) as Record<string, unknown>);
+    const assistantEntries = transcriptLines.filter(
+      (entry) =>
+        (entry as { message?: { role?: string } }).message?.role === "assistant" ||
+        (entry as { role?: string }).role === "assistant",
+    );
+    expect(assistantEntries).toEqual([]);
   });
 
   it("keeps visible text on non-agent TTS final media because no model transcript exists", async () => {