diff --git a/CHANGELOG.md b/CHANGELOG.md
index 40ff2a16203..2965b5062d4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -130,7 +130,7 @@ Docs: https://docs.openclaw.ai
 - Discord: keep REST, webhook, and monitor traffic on the configured proxy, preserve component-only media sends, honor `@everyone` and `@here` mention gates, keep ACK reactions on the active account, and split voice connect/playback timeouts so auto-join is more reliable. (#57465, #60361, #60345) Thanks @geekhuashan.
 - WhatsApp: restore `channels.whatsapp.blockStreaming` and reset watchdog timeouts after reconnect so quiet chats stop falling into reconnect loops. (#60007, #60069) Thanks @MonkeyLeeT and @mcaxtr.
 - Memory: keep `memory-core` builtin embedding registration on the already-registered path so selecting `memory-core` no longer recurses through plugin discovery and crashes during startup. (#61402) Thanks @ngutman.
-- Agents/tool results: keep large `read` outputs visible longer and preserve the latest `read` output during tool-result context compaction so fresh file reads stop getting replaced by compacted stubs when older tool output can absorb the overflow budget. Thanks @vincentkoc.
+- Agents/tool results: keep large `read` outputs visible longer, preserve the latest `read` output when older tool output can absorb the overflow budget, and fall back to Pi's normal overflow compaction/retry path before replacing a fresh `read` with a compacted stub. Thanks @vincentkoc.
 - Memory/QMD: prefer modern `qmd collection add --glob`, accept newer single-line JSON hit metadata while keeping legacy line fields, refresh QMD docs/doctor install guidance and model-override guidance, and keep older QMD releases working. Thanks @vincentkoc.
 - MS Teams: download inline DM images via Graph API and preserve channel reply threading in proactive fallback. (#52212, #55198) Thanks @Ted-developer and @hyojin.
 - MS Teams: replace the deprecated Teams SDK HttpPlugin stub with `httpServerAdapter` so recurring gateway deprecation warnings stop firing and the Express 5 compatibility workaround stays on the supported SDK path. (#60939) Thanks @coolramukaka-sys.
diff --git a/src/agents/pi-embedded-runner/tool-result-context-guard.test.ts b/src/agents/pi-embedded-runner/tool-result-context-guard.test.ts
index fb80de18478..33ffaf10293 100644
--- a/src/agents/pi-embedded-runner/tool-result-context-guard.test.ts
+++ b/src/agents/pi-embedded-runner/tool-result-context-guard.test.ts
@@ -17,17 +17,21 @@ function makeUser(text: string): AgentMessage {
   });
 }
 
-function makeToolResult(id: string, text: string): AgentMessage {
+function makeToolResult(id: string, text: string, toolName = "grep"): AgentMessage {
   return castAgentMessage({
     role: "toolResult",
     toolCallId: id,
-    toolName: "read",
+    toolName,
     content: [{ type: "text", text }],
     isError: false,
     timestamp: Date.now(),
   });
 }
 
+function makeReadToolResult(id: string, text: string): AgentMessage {
+  return makeToolResult(id, text, "read");
+}
+
 function makeLegacyToolResult(id: string, text: string): AgentMessage {
   return castAgentMessage({
     role: "tool",
@@ -311,6 +315,51 @@ describe("installToolResultContextGuard", () => {
     expect(newResult.details).toBeUndefined();
   });
 
+  it("throws overflow instead of compacting the latest read result during aggregate compaction", async () => {
+    const agent = makeGuardableAgent();
+
+    installToolResultContextGuard({
+      agent,
+      contextWindowTokens: 1_000,
+    });
+
+    const contextForNextCall = [
+      makeUser("u".repeat(2_600)),
+      makeToolResult("call_old", "x".repeat(300)),
+      makeReadToolResult("call_new", "y".repeat(500)),
+    ];
+
+    await expect(
+      agent.transformContext?.(contextForNextCall, new AbortController().signal),
+    ).rejects.toThrow(PREEMPTIVE_CONTEXT_OVERFLOW_MESSAGE);
+
+    expect(getToolResultText(contextForNextCall[1])).toBe("x".repeat(300));
+    expect(getToolResultText(contextForNextCall[2])).toBe("y".repeat(500));
+  });
+
+  it("keeps the latest read result when older outputs absorb the aggregate overflow", async () => {
+    const agent = makeGuardableAgent();
+
+    installToolResultContextGuard({
+      agent,
+      contextWindowTokens: 1_000,
+    });
+
+    const contextForNextCall = [
+      makeUser("u".repeat(1_400)),
+      makeToolResult("call_old_1", "a".repeat(350)),
+      makeToolResult("call_old_2", "b".repeat(350)),
+      makeReadToolResult("call_new", "c".repeat(500)),
+    ];
+
+    const transformed = (await agent.transformContext?.(
+      contextForNextCall,
+      new AbortController().signal,
+    )) as AgentMessage[];
+
+    expect(getToolResultText(transformed[3])).toBe("c".repeat(500));
+  });
+
   it("throws preemptive context overflow when context exceeds 90% after tool-result compaction", async () => {
     const agent = makeGuardableAgent();
 
diff --git a/src/agents/pi-embedded-runner/tool-result-context-guard.ts b/src/agents/pi-embedded-runner/tool-result-context-guard.ts
index 42177eca6e9..407a9471e62 100644
--- a/src/agents/pi-embedded-runner/tool-result-context-guard.ts
+++ b/src/agents/pi-embedded-runner/tool-result-context-guard.ts
@@ -49,6 +49,21 @@ type GuardableAgentRecord = {
   transformContext?: GuardableTransformContext;
 };
 
+function getToolResultName(msg: AgentMessage): string | undefined {
+  const toolName = (msg as { toolName?: unknown }).toolName;
+  if (typeof toolName === "string" && toolName.trim().length > 0) {
+    return toolName;
+  }
+  const legacyToolName = (msg as { tool_name?: unknown }).tool_name;
+  return typeof legacyToolName === "string" && legacyToolName.trim().length > 0
+    ? legacyToolName
+    : undefined;
+}
+
+function isReadToolResultMessage(msg: AgentMessage): boolean {
+  return isToolResultMessage(msg) && getToolResultName(msg) === "read";
+}
+
 function truncateTextToBudget(text: string, maxChars: number): string {
   if (text.length <= maxChars) {
     return text;
@@ -278,6 +293,65 @@ function resolveToolResultCompactionOrder(messages: AgentMessage[]): number[] {
   return [...olderIndexes, newestIndex];
 }
 
+function getNewestToolResultIndex(messages: AgentMessage[]): number | undefined {
+  for (let i = messages.length - 1; i >= 0; i -= 1) {
+    if (isToolResultMessage(messages[i])) {
+      return i;
+    }
+  }
+  return undefined;
+}
+
+function shouldPreferOverflowForLatestRead(params: {
+  messages: AgentMessage[];
+  contextBudgetChars: number;
+  maxSingleToolResultChars: number;
+}): boolean {
+  const newestToolResultIndex = getNewestToolResultIndex(params.messages);
+  if (newestToolResultIndex === undefined) {
+    return false;
+  }
+  const newestToolResult = params.messages[newestToolResultIndex];
+  if (!isReadToolResultMessage(newestToolResult)) {
+    return false;
+  }
+
+  const initialCache = createMessageCharEstimateCache();
+  if (
+    estimateMessageCharsCached(newestToolResult, initialCache) > params.maxSingleToolResultChars
+  ) {
+    return false;
+  }
+
+  const simulatedMessages = cloneMessagesForGuard(params.messages);
+  const estimateCache = createMessageCharEstimateCache();
+  for (const message of simulatedMessages) {
+    if (!isToolResultMessage(message)) {
+      continue;
+    }
+    const truncated = truncateToolResultToChars(
+      message,
+      params.maxSingleToolResultChars,
+      estimateCache,
+    );
+    applyMessageMutationInPlace(message, truncated, estimateCache);
+  }
+
+  const currentChars = estimateContextChars(simulatedMessages, estimateCache);
+  if (currentChars <= params.contextBudgetChars) {
+    return false;
+  }
+
+  const newestToolResultAfterPerToolLimit = simulatedMessages[newestToolResultIndex];
+  const newestToolResultTextBefore = getToolResultText(newestToolResultAfterPerToolLimit);
+  compactExistingToolResultsInPlace({
+    messages: simulatedMessages,
+    charsNeeded: currentChars - params.contextBudgetChars,
+    cache: estimateCache,
+  });
+  return getToolResultText(simulatedMessages[newestToolResultIndex]) !== newestToolResultTextBefore;
+}
+
 function cloneMessagesForGuard(messages: AgentMessage[]): AgentMessage[] {
   return messages.map(
     (msg) => ({ ...(msg as unknown as Record<string, unknown>) }) as unknown as AgentMessage,
@@ -388,6 +462,15 @@ export function installToolResultContextGuard(params: {
       : messages;
 
     const sourceMessages = Array.isArray(transformed) ? transformed : messages;
+    if (
+      shouldPreferOverflowForLatestRead({
+        messages: sourceMessages,
+        contextBudgetChars,
+        maxSingleToolResultChars,
+      })
+    ) {
+      throw new Error(PREEMPTIVE_CONTEXT_OVERFLOW_MESSAGE);
+    }
     const contextMessages = contextNeedsToolResultCompaction({
       messages: sourceMessages,
       contextBudgetChars,