diff --git a/orchestrate/skills/orchestrate/scripts/__tests__/redact-body.test.ts b/orchestrate/skills/orchestrate/scripts/__tests__/redact-body.test.ts
index a7fbbd4a..cb990afe 100644
--- a/orchestrate/skills/orchestrate/scripts/__tests__/redact-body.test.ts
+++ b/orchestrate/skills/orchestrate/scripts/__tests__/redact-body.test.ts
@@ -41,6 +41,45 @@ describe("redactBody", () => {
     expect(redactBody(`\`${sha}\``).reasons).toEqual([]);
   });
 
+  test("redacts quoted JSON keys and values containing spaces", () => {
+    // The old pattern used \b around the key, so a quote-adjacent key like
+    // "api_key" in a pasted JSON body never matched and the secret went out
+    // unredacted. It also stopped the value at the first space, leaking
+    // `Bearer <jwt>` tails.
+    expect(
+      redactBody('{"Authorization": "Bearer eyJhbG.sig"}').text
+    ).toContain("Authorization=[redacted]");
+    expect(
+      redactBody('{"api_key": "sk-123", "name": "x"}').text
+    ).not.toContain("sk-123");
+    expect(redactBody('api_key = "super secret value"').text).toBe(
+      'api_key=[redacted]'
+    );
+  });
+
+  test("redacts unquoted values up to a separator, consuming it", () => {
+    // Cursor Bugbot flagged the first cut: the value pattern stopped at
+    // `,`/`;`/`}` without consuming them, so an unquoted assignment failed to
+    // match entirely and the raw secret passed through.
+    const result = redactBody("password: hunter2, keep");
+    expect(result.text).toBe("password=[redacted] keep");
+    expect(redactBody("token = abc123; next=1").text).toBe(
+      "token=[redacted] next=1"
+    );
+  });
+
+  test("does not truncate a quoted value at an inner apostrophe", () => {
+    // Bugbot round 2: the first fix merged `"` and `'` into one character
+    // class, so a double-quoted value containing an apostrophe ended at it and
+    // leaked the secret tail. The opening quote must decide the closing quote.
+    expect(
+      redactBody(`{"password": "it's a secret123"}`).text
+    ).toBe("{password=[redacted]}");
+    expect(redactBody(`{"token": "don't-panic"}`).text).toBe(
+      "{token=[redacted]}"
+    );
+  });
+
   test("allows concise operational context", () => {
     const result = redactBody("blocked: docker rate-limit on redis:7");
 
diff --git a/orchestrate/skills/orchestrate/scripts/core/redact-body.ts b/orchestrate/skills/orchestrate/scripts/core/redact-body.ts
index 4623f107..00cf1e3a 100644
--- a/orchestrate/skills/orchestrate/scripts/core/redact-body.ts
+++ b/orchestrate/skills/orchestrate/scripts/core/redact-body.ts
@@ -1,7 +1,15 @@
 const MAX_BODY_CHARS = 2_048;
 const SENSITIVE_KEY_RE = /token|secret|password|api[_-]?key|authorization/i;
 const SENSITIVE_ASSIGNMENT_RE =
-  /\b(token|secret|password|api[_-]?key|authorization)\b\s*[:=]\s*\S+/gi;
+  /"?((?:[\w.-]+\/)?(?:token|secret|password|api[_-]?key|authorization)[\w.-]*)"?\s*[:=]\s*/gi;
+// The value is matched up to a real assignment boundary and redacted whole:
+//  - a double-quoted value runs to its closing `"` (escaped quotes allowed), so a
+//    quoted value containing an apostrophe is not truncated at it;
+//  - a single-quoted value runs to its closing `'` (escaped quotes allowed);
+//  - an unquoted value runs to `,`/`;`/`}`/end-of-line, consuming one optional
+//    terminator so the assignment ends at a real boundary (Bugbot round 1).
+const SENSITIVE_VALUE_RE =
+  /(?:"(?:\\.|[^"\\])*"?|'(?:\\.|[^'\\])*'?|[^,;}\n]*[,;}]?)/;
 const PATH_PATTERNS = [
   { re: /^\/workspace\/\S*/gm, reason: "contains /workspace path" },
   { re: /^\/Users\/\S*/gm, reason: "contains /Users path" },
@@ -33,14 +41,16 @@ function redactSensitiveAssignments(
   text: string,
   reasons: Set<string>
 ): string {
-  return text.replace(SENSITIVE_ASSIGNMENT_RE, match => {
-    const [key] = match.split(/\s*[:=]\s*/, 1);
-    if (SENSITIVE_KEY_RE.test(key ?? "")) {
-      reasons.add("contains sensitive key");
-      return `${key}=[redacted]`;
+  return text.replace(
+    new RegExp(SENSITIVE_ASSIGNMENT_RE.source + SENSITIVE_VALUE_RE.source, "gi"),
+    (match, key: string | undefined) => {
+      if (SENSITIVE_KEY_RE.test(key ?? "")) {
+        reasons.add("contains sensitive key");
+        return `${key}=[redacted]`;
+      }
+      return match;
     }
-    return match;
-  });
+  );
 }
 
 function redactPaths(text: string, reasons: Set<string>): string {