diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3fc07ffb059..d206e228cae 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ Docs: https://docs.openclaw.ai
 
 - Docs/Web search: remove outdated Brave free-tier wording and replace prescriptive AI ToS guidance with neutral compliance language in Brave setup docs. (#26860) Thanks @HenryLoenwind.
 - Tools/Diffs guidance loading: move diffs usage guidance from unconditional prompt-hook injection to the plugin companion skill path, reducing unrelated-turn prompt noise while keeping diffs tool behavior unchanged. (#32630) thanks @sircrumpet.
+- Agents/tool-result truncation: preserve important tail diagnostics by using head+tail truncation for oversized tool results while keeping configurable truncation options. (#20076) thanks @jlwestsr.
 
 ### Fixes
 
diff --git a/src/agents/pi-embedded-runner/tool-result-truncation.test.ts b/src/agents/pi-embedded-runner/tool-result-truncation.test.ts
index a606d977ba1..8b4fbb628c6 100644
--- a/src/agents/pi-embedded-runner/tool-result-truncation.test.ts
+++ b/src/agents/pi-embedded-runner/tool-result-truncation.test.ts
@@ -289,3 +289,25 @@ describe("sessionLikelyHasOversizedToolResults", () => {
     ).toBe(false);
   });
 });
+
+describe("truncateToolResultText head+tail strategy", () => {
+  it("preserves error content at the tail when present", () => {
+    const head = "Line 1\n".repeat(500);
+    const middle = "data data data\n".repeat(500);
+    const tail = "\nError: something failed\nStack trace: at foo.ts:42\n";
+    const text = head + middle + tail;
+    const result = truncateToolResultText(text, 5000);
+    // Should contain both the beginning and the error at the end
+    expect(result).toContain("Line 1");
+    expect(result).toContain("Error: something failed");
+    expect(result).toContain("middle content omitted");
+  });
+
+  it("uses simple head truncation when tail has no important content", () => {
+    const text = "normal line\n".repeat(1000);
+    const result = truncateToolResultText(text, 5000);
+    expect(result).toContain("normal line");
+    expect(result).not.toContain("middle content omitted");
+    expect(result).toContain("truncated");
+  });
+});
diff --git a/src/agents/pi-embedded-runner/tool-result-truncation.ts b/src/agents/pi-embedded-runner/tool-result-truncation.ts
index 05bce138868..c8cbd1124bb 100644
--- a/src/agents/pi-embedded-runner/tool-result-truncation.ts
+++ b/src/agents/pi-embedded-runner/tool-result-truncation.ts
@@ -39,7 +39,34 @@ type ToolResultTruncationOptions = {
 };
 
 /**
- * Truncate a single text string to fit within maxChars, preserving the beginning.
+ * Marker inserted between head and tail when using head+tail truncation.
+ */
+const MIDDLE_OMISSION_MARKER =
+  "\n\n⚠️ [... middle content omitted — showing head and tail ...]\n\n";
+
+/**
+ * Detect whether text likely contains error/diagnostic content near the end,
+ * which should be preserved during truncation.
+ */
+function hasImportantTail(text: string): boolean {
+  // Check last ~2000 chars for error-like patterns
+  const tail = text.slice(-2000).toLowerCase();
+  return (
+    /\b(error|exception|failed|fatal|traceback|panic|stack trace|errno|exit code)\b/.test(tail) ||
+    // JSON closing — if the output is JSON, the tail has closing structure
+    /\}\s*$/.test(tail.trim()) ||
+    // Summary/result lines often appear at the end
+    /\b(total|summary|result|complete|finished|done)\b/.test(tail)
+  );
+}
+
+/**
+ * Truncate a single text string to fit within maxChars.
+ *
+ * Uses a head+tail strategy when the tail contains important content
+ * (errors, results, JSON structure), otherwise preserves the beginning.
+ * This ensures error messages and summaries at the end of tool output
+ * aren't lost during truncation.
  */
 export function truncateToolResultText(
   text: string,
@@ -51,11 +78,35 @@ export function truncateToolResultText(
   if (text.length <= maxChars) {
     return text;
   }
-  const keepChars = Math.max(minKeepChars, maxChars - suffix.length);
-  // Try to break at a newline boundary to avoid cutting mid-line
-  let cutPoint = keepChars;
-  const lastNewline = text.lastIndexOf("\n", keepChars);
-  if (lastNewline > keepChars * 0.8) {
+  const budget = Math.max(minKeepChars, maxChars - suffix.length);
+
+  // If tail looks important, split budget between head and tail
+  if (hasImportantTail(text) && budget > minKeepChars * 2) {
+    const tailBudget = Math.min(Math.floor(budget * 0.3), 4_000);
+    const headBudget = budget - tailBudget - MIDDLE_OMISSION_MARKER.length;
+
+    if (headBudget > minKeepChars) {
+      // Find clean cut points at newline boundaries
+      let headCut = headBudget;
+      const headNewline = text.lastIndexOf("\n", headBudget);
+      if (headNewline > headBudget * 0.8) {
+        headCut = headNewline;
+      }
+
+      let tailStart = text.length - tailBudget;
+      const tailNewline = text.indexOf("\n", tailStart);
+      if (tailNewline !== -1 && tailNewline < tailStart + tailBudget * 0.2) {
+        tailStart = tailNewline + 1;
+      }
+
+      return text.slice(0, headCut) + MIDDLE_OMISSION_MARKER + text.slice(tailStart) + suffix;
+    }
+  }
+
+  // Default: keep the beginning
+  let cutPoint = budget;
+  const lastNewline = text.lastIndexOf("\n", budget);
+  if (lastNewline > budget * 0.8) {
     cutPoint = lastNewline;
   }
   return text.slice(0, cutPoint) + suffix;