diff --git a/src/engine/redaction.ts b/src/engine/redaction.ts
index 5d3daa2..f4750f2 100644
--- a/src/engine/redaction.ts
+++ b/src/engine/redaction.ts
@@ -79,12 +79,39 @@ export function redact(input: string): string {
   return out;
 }
 
-/** Redact and cap length so a runaway log can't blow up a critic call. */
+/**
+ * Redact and cap length so a runaway log can't blow up a critic call.
+ *
+ * Structure-aware (inspired by pi's harness `truncate.ts`): when the content
+ * has line structure — diffs, build/test output — the head is snapped back to
+ * the last line boundary within budget and the tail forward to the next one, so
+ * the critic never reasons over a line cut mid-token. The elision marker
+ * reports how much (chars and lines) was dropped. A single very long line with
+ * no boundaries falls back to a hard head/tail char slice.
+ */
 export function redactAndTruncate(input: string, maxChars = 8_000): string {
   const redacted = redact(input);
   if (redacted.length <= maxChars) return redacted;
-  const head = redacted.slice(0, Math.floor(maxChars * 0.7));
-  const tail = redacted.slice(-Math.floor(maxChars * 0.2));
-  const omitted = redacted.length - head.length - tail.length;
-  return `${head}\n...[${omitted} chars truncated]...\n${tail}`;
+
+  const headBudget = Math.floor(maxChars * 0.7);
+  const tailBudget = Math.floor(maxChars * 0.2);
+
+  // Head: take the budget, then trim back to the last complete line.
+  let head = redacted.slice(0, headBudget);
+  const headNl = head.lastIndexOf("\n");
+  if (headNl >= 0) head = head.slice(0, headNl);
+
+  // Tail: take the budget from the end, then trim forward to start of a line.
+  let tail = redacted.slice(redacted.length - tailBudget);
+  const tailNl = tail.indexOf("\n");
+  if (tailNl >= 0) tail = tail.slice(tailNl + 1);
+
+  const omittedChars = redacted.length - head.length - tail.length;
+  if (omittedChars <= 0) return redacted; // budgets overlapped; nothing to drop
+
+  const omittedLines =
+    redacted.slice(head.length, redacted.length - tail.length).split("\n").length - 1;
+  const linesPart = omittedLines > 0 ? ` / ${omittedLines} lines` : "";
+
+  return `${head}\n...[${omittedChars} chars${linesPart} truncated]...\n${tail}`;
 }
diff --git a/test/redaction.test.ts b/test/redaction.test.ts
index b2bcd21..1de5998 100644
--- a/test/redaction.test.ts
+++ b/test/redaction.test.ts
@@ -40,6 +40,43 @@ describe("redaction", () => {
     expect(out).toContain("END");
     expect(out).toContain("truncated");
   });
+
+  it("truncates multi-line output on line boundaries, reporting omitted lines", () => {
+    const lines = Array.from({ length: 300 }, (_, i) => `line-${i}: ${"y".repeat(40)}`);
+    const out = redactAndTruncate(lines.join("\n"), 600);
+
+    expect(out).toContain("line-0:"); // first line kept
+    expect(out).toContain("line-299:"); // last line kept
+    expect(out).toContain("lines truncated");
+    expect(out).not.toContain("line-150:"); // a middle line dropped
+
+    // Every retained line in the head/tail segments is complete (no mid-line cut).
+    const segments = out.split(/\n\.\.\.\[[^\]]*\]\.\.\.\n/);
+    expect(segments).toHaveLength(2);
+    for (const seg of segments) {
+      for (const ln of seg.split("\n").filter(Boolean)) {
+        expect(ln).toMatch(/^line-\d+: y{40}$/);
+      }
+    }
+  });
+
+  it("falls back to a hard char slice for a single very long line", () => {
+    const big = "START" + "x".repeat(5_000) + "END";
+    const out = redactAndTruncate(big, 500);
+    expect(out).toContain("START");
+    expect(out).toContain("END");
+    expect(out).toContain("truncated");
+    expect(out.length).toBeLessThan(1_000);
+  });
+
+  it("still redacts secrets in the retained head/tail after truncation", () => {
+    const text =
+      "OPENAI_API_KEY=sk-abcdef0123456789abcdef\n" + "log line\n".repeat(2_000) + "trailing FOO=bar";
+    const out = redactAndTruncate(text, 400);
+    expect(out).toContain("OPENAI_API_KEY=[REDACTED]");
+    expect(out).not.toContain("sk-abcdef");
+    expect(out).toContain("trailing FOO=bar");
+  });
 });