diff --git a/src/lib/utils/json/coerce.ts b/src/lib/utils/json/coerce.ts
index 5f261d62c..bf787dc6a 100644
--- a/src/lib/utils/json/coerce.ts
+++ b/src/lib/utils/json/coerce.ts
@@ -56,6 +56,78 @@ function parseOrRepair(
   }
 }
 
+/** Bounds the recursive nested-string unwrap against pathological inputs. */
+const MAX_NESTED_UNWRAP_DEPTH = 6;
+
+/**
+ * Recursively replace any string-valued field whose content is itself a JSON
+ * object/array with the parsed value. Models sometimes double-encode a NESTED
+ * field — e.g. `{ "attachment": "{\"k\":1}" }` instead of
+ * `{ "attachment": { "k": 1 } }` — which fails schema validation even though the
+ * intended object is right there. (`coerceJsonToSchema` already unwraps a
+ * stringified TOP-LEVEL object; this handles the nested case.)
+ *
+ * A parsed string is NOT re-descended into: its own string fields (e.g. an
+ * attachment's `content`) are the model's intended values and must be left
+ * alone. Recursion only walks already-structural objects/arrays to find
+ * stringified fields anywhere in the tree. Returns a NEW value (never mutates
+ * the input) plus whether anything changed, so the caller can skip a redundant
+ * re-validation when nothing was unwrapped. Callers MUST re-validate the result
+ * against the schema — that gate is what keeps an over-eager unwrap (a field
+ * that should stay a string) from being accepted.
+ */
+function deepUnwrapJsonStrings(
+  value: unknown,
+  depth = 0,
+): { value: unknown; changed: boolean } {
+  if (depth > MAX_NESTED_UNWRAP_DEPTH) {
+    return { value, changed: false };
+  }
+  if (typeof value === "string") {
+    const s = value.trim();
+    const looksJson =
+      (s.startsWith("{") && s.endsWith("}")) ||
+      (s.startsWith("[") && s.endsWith("]"));
+    if (looksJson) {
+      try {
+        const parsed: unknown = JSON.parse(s);
+        if (parsed !== null && typeof parsed === "object") {
+          // Parsed one stringified layer. Do NOT descend into `parsed` — its
+          // own string fields are intended values, not double-encodings.
+          return { value: parsed, changed: true };
+        }
+      } catch {
+        // not JSON — leave the string as-is
+      }
+    }
+    return { value, changed: false };
+  }
+  if (Array.isArray(value)) {
+    let changed = false;
+    const out = value.map((item) => {
+      const r = deepUnwrapJsonStrings(item, depth + 1);
+      if (r.changed) {
+        changed = true;
+      }
+      return r.value;
+    });
+    return { value: changed ? out : value, changed };
+  }
+  if (value !== null && typeof value === "object") {
+    let changed = false;
+    const out: Record<string, unknown> = {};
+    for (const [k, v] of Object.entries(value as Record<string, unknown>)) {
+      const r = deepUnwrapJsonStrings(v, depth + 1);
+      if (r.changed) {
+        changed = true;
+      }
+      out[k] = r.value;
+    }
+    return { value: changed ? out : value, changed };
+  }
+  return { value, changed: false };
+}
+
 /**
  * Try to produce canonical JSON from `text`. Returns null when no JSON object
  * could be recovered (caller should then keep the raw text).
@@ -170,6 +242,25 @@ export function coerceJsonToSchema(
     };
     if (safeParseable.safeParse(outcome.value).success) {
       schemaValid.push(record);
+    } else {
+      // The model may have double-encoded a NESTED field as a JSON string
+      // (e.g. `{"attachment":"{...}"}` instead of `{"attachment":{...}}`),
+      // which fails validation even though the intended object is present.
+      // Unwrap stringified object/array fields and re-validate before giving
+      // up — the safeParse gate rejects any over-eager unwrap.
+      const unwrapped = deepUnwrapJsonStrings(outcome.value);
+      if (
+        unwrapped.changed &&
+        unwrapped.value !== null &&
+        typeof unwrapped.value === "object" &&
+        safeParseable.safeParse(unwrapped.value).success
+      ) {
+        schemaValid.push({
+          value: unwrapped.value,
+          repaired: true,
+          truncated: candidate.truncated,
+        });
+      }
     }
   }
 
diff --git a/test/continuous-test-suite-coerce-nested-unwrap.ts b/test/continuous-test-suite-coerce-nested-unwrap.ts
new file mode 100644
index 000000000..0957ea555
--- /dev/null
+++ b/test/continuous-test-suite-coerce-nested-unwrap.ts
@@ -0,0 +1,145 @@
+#!/usr/bin/env tsx
+/**
+ * Continuous Test Suite: coerce deep-unwrap of nested stringified JSON (no API).
+ *
+ * Models sometimes double-encode a NESTED field as a JSON *string* —
+ * `{ "attachment": "{...}" }` instead of `{ "attachment": { ... } }` — which
+ * fails schema validation even though the intended object is right there. This
+ * was observed in production (Tara's `{summary, attachment}` envelope): the
+ * `attachment` came back as a JSON string, so the declared `pdf` was lost and
+ * the content degraded to a markdown/text file.
+ *
+ * coerceJsonToSchema already unwraps a stringified TOP-LEVEL object; this suite
+ * locks in the NESTED-field unwrap: when no candidate passes the schema, string
+ * fields that are themselves JSON objects/arrays are parsed and the result is
+ * re-validated. Crucially, the re-validation gate prevents over-unwrapping a
+ * field that should stay a string, and a parsed object is not re-descended into
+ * (so an attachment's own `content` is preserved verbatim).
+ *
+ * Run: npx tsx test/continuous-test-suite-coerce-nested-unwrap.ts
+ */
+import { z } from "zod";
+import { defineSuite, assertEqual } from "./helpers/harness.js";
+import { coerceJsonToSchema } from "../src/lib/utils/json/coerce.js";
+
+const { test, runSuite } = defineSuite(
+  "Coerce nested stringified-object unwrap",
+);
+
+// Mirrors curator's StructuredAgentResponseSchema: attachment must be a nested
+// object (or null) with string fields.
+const schema = z.object({
+  summary: z.string().min(1),
+  attachment: z
+    .object({
+      filename: z.string(),
+      extension: z.string(),
+      mimetype: z.string(),
+      content: z.string(),
+    })
+    .nullable(),
+});
+
+const obj = (
+  r: ReturnType<typeof coerceJsonToSchema>,
+): Record<string, unknown> =>
+  (r?.structuredData ?? {}) as Record<string, unknown>;
+const att = (
+  r: ReturnType<typeof coerceJsonToSchema>,
+): Record<string, unknown> =>
+  (obj(r).attachment ?? {}) as Record<string, unknown>;
+
+await test("unwraps a stringified nested attachment object (the production bug)", () => {
+  const attachment = {
+    filename: "tara_structural_response_test",
+    extension: "pdf",
+    mimetype: "application/pdf",
+    content: "# Report\n\nbody",
+  };
+  const text = JSON.stringify({
+    summary: "done",
+    attachment: JSON.stringify(attachment),
+  });
+  const r = coerceJsonToSchema(text, schema);
+  assertEqual(
+    typeof att(r).filename,
+    "string",
+    "attachment became a real object",
+  );
+  assertEqual(att(r).extension, "pdf", "declared extension recovered");
+  assertEqual(att(r).content, "# Report\n\nbody", "content preserved");
+});
+
+await test("does not re-descend into the parsed object: JSON-looking content stays a string", () => {
+  const attachment = {
+    filename: "data",
+    extension: "json",
+    mimetype: "application/json",
+    content: '{"x":1}', // legitimately a JSON string as the file's content
+  };
+  const text = JSON.stringify({
+    summary: "done",
+    attachment: JSON.stringify(attachment),
+  });
+  const r = coerceJsonToSchema(text, schema);
+  assertEqual(
+    typeof att(r).filename,
+    "string",
+    "attachment unwrapped to object",
+  );
+  assertEqual(
+    att(r).content,
+    '{"x":1}',
+    "content kept as a string, not re-parsed",
+  );
+});
+
+await test("a clean nested object passes through unchanged (no unwrap needed)", () => {
+  const clean = {
+    summary: "ok",
+    attachment: {
+      filename: "f",
+      extension: "md",
+      mimetype: "text/markdown",
+      content: "x",
+    },
+  };
+  const r = coerceJsonToSchema(JSON.stringify(clean), schema);
+  assertEqual(att(r).filename, "f", "clean object preserved");
+  assertEqual(att(r).extension, "md", "clean extension preserved");
+});
+
+await test("null attachment is preserved", () => {
+  const r = coerceJsonToSchema(
+    JSON.stringify({ summary: "hi", attachment: null }),
+    schema,
+  );
+  assertEqual(obj(r).attachment, null, "null attachment preserved");
+});
+
+await test("does NOT unwrap a JSON-looking value that is validly a string", () => {
+  // summary is a string that happens to look like JSON; the schema wants a
+  // string, so the direct parse already validates and deep-unwrap never runs.
+  const summaryStr = '{"not":"a real summary object"}';
+  const r = coerceJsonToSchema(
+    JSON.stringify({ summary: summaryStr, attachment: null }),
+    schema,
+  );
+  assertEqual(
+    obj(r).summary,
+    summaryStr,
+    "JSON-looking summary kept as a string",
+  );
+});
+
+await test("no schema → nested string is left untouched (first parseable wins)", () => {
+  const text = JSON.stringify({ summary: "x", attachment: '{"a":1}' });
+  const r = coerceJsonToSchema(text); // no schema to gate an unwrap
+  assertEqual(
+    typeof obj(r).attachment,
+    "string",
+    "without a schema, the nested string is not unwrapped",
+  );
+});
+
+await runSuite();