diff --git a/src/agents/pi-embedded-runner/compact.ts b/src/agents/pi-embedded-runner/compact.ts
index 280e7d0aba..84a0c61661 100644
--- a/src/agents/pi-embedded-runner/compact.ts
+++ b/src/agents/pi-embedded-runner/compact.ts
@@ -44,6 +44,7 @@ import { createOpenClawCodingTools } from "../pi-tools.js";
 import { resolveSandboxContext } from "../sandbox.js";
 import { repairSessionFileIfNeeded } from "../session-file-repair.js";
 import { guardSessionManager } from "../session-tool-result-guard-wrapper.js";
+import { sanitizeToolUseResultPairing } from "../session-transcript-repair.js";
 import { acquireSessionWriteLock } from "../session-write-lock.js";
 import { detectRuntimeShell } from "../shell-utils.js";
 import {
@@ -429,10 +430,16 @@ export async function compactEmbeddedPiSessionDirect(
         const validated = transcriptPolicy.validateAnthropicTurns
           ? validateAnthropicTurns(validatedGemini)
           : validatedGemini;
-        const limited = limitHistoryTurns(
+        const truncated = limitHistoryTurns(
           validated,
           getDmHistoryLimitFromSessionKey(params.sessionKey, params.config),
         );
+        // Re-run tool_use/tool_result pairing repair after truncation, since
+        // limitHistoryTurns can orphan tool_result blocks by removing the
+        // assistant message that contained the matching tool_use.
+        const limited = transcriptPolicy.repairToolUseResultPairing
+          ? sanitizeToolUseResultPairing(truncated)
+          : truncated;
         if (limited.length > 0) {
           session.agent.replaceMessages(limited);
         }
diff --git a/src/agents/pi-embedded-runner/run/attempt.ts b/src/agents/pi-embedded-runner/run/attempt.ts
index 086b11fae1..893bcbc671 100644
--- a/src/agents/pi-embedded-runner/run/attempt.ts
+++ b/src/agents/pi-embedded-runner/run/attempt.ts
@@ -48,6 +48,7 @@ import { resolveSandboxContext } from "../../sandbox.js";
 import { resolveSandboxRuntimeStatus } from "../../sandbox/runtime-status.js";
 import { repairSessionFileIfNeeded } from "../../session-file-repair.js";
 import { guardSessionManager } from "../../session-tool-result-guard-wrapper.js";
+import { sanitizeToolUseResultPairing } from "../../session-transcript-repair.js";
 import { acquireSessionWriteLock } from "../../session-write-lock.js";
 import { detectRuntimeShell } from "../../shell-utils.js";
 import {
@@ -556,10 +557,16 @@ export async function runEmbeddedAttempt(
         const validated = transcriptPolicy.validateAnthropicTurns
           ? validateAnthropicTurns(validatedGemini)
           : validatedGemini;
-        const limited = limitHistoryTurns(
+        const truncated = limitHistoryTurns(
           validated,
           getDmHistoryLimitFromSessionKey(params.sessionKey, params.config),
         );
+        // Re-run tool_use/tool_result pairing repair after truncation, since
+        // limitHistoryTurns can orphan tool_result blocks by removing the
+        // assistant message that contained the matching tool_use.
+        const limited = transcriptPolicy.repairToolUseResultPairing
+          ? sanitizeToolUseResultPairing(truncated)
+          : truncated;
         cacheTrace?.recordStage("session:limited", { messages: limited });
         if (limited.length > 0) {
           activeSession.agent.replaceMessages(limited);