diff --git a/rest/nodejs/src/api/checkout.ts b/rest/nodejs/src/api/checkout.ts
index 2e453fcf..2eca3986 100644
--- a/rest/nodejs/src/api/checkout.ts
+++ b/rest/nodejs/src/api/checkout.ts
@@ -153,6 +153,8 @@ export class CheckoutService {
         headers: {
           "Content-Type": "application/json",
           "X-Event-Type": eventType,
+          "Webhook-Id": uuidv4(),
+          "Webhook-Timestamp": Math.floor(Date.now() / 1000).toString(),
         },
         body: JSON.stringify(orderData),
       });
diff --git a/rest/nodejs/test/webhook.test.ts b/rest/nodejs/test/webhook.test.ts
index 3dfad0da..e5d62a76 100644
--- a/rest/nodejs/test/webhook.test.ts
+++ b/rest/nodejs/test/webhook.test.ts
@@ -118,6 +118,29 @@ test("webhook delivers the bare order object as the body", async () => {
     "event type must be carried in the X-Event-Type header"
   );
 
+  assert.ok(
+    delivered.headers["Webhook-Id"],
+    "Webhook-Id header must be present"
+  );
+  const uuidRegex =
+    /^[0-9a-f]{8}-[0-9a-f]{4}-[1-5][0-9a-f]{3}-[89ab][0-9a-f]{3}-[0-9a-f]{12}$/i;
+  assert.ok(
+    uuidRegex.test(delivered.headers["Webhook-Id"]),
+    "Webhook-Id must be a valid UUID"
+  );
+
+  assert.ok(
+    delivered.headers["Webhook-Timestamp"],
+    "Webhook-Timestamp header must be present"
+  );
+  const timestamp = parseInt(delivered.headers["Webhook-Timestamp"], 10);
+  assert.ok(!isNaN(timestamp), "Webhook-Timestamp must be a number");
+  const now = Math.floor(Date.now() / 1000);
+  assert.ok(
+    Math.abs(now - timestamp) < 5,
+    `Webhook-Timestamp (${timestamp}) should be close to now (${now})`
+  );
+
   const body = delivered.body as Record<string, unknown>;
   // The body IS the order: its own id, and every required field present.
   assert.equal(
diff --git a/rest/python/server/exceptions.py b/rest/python/server/exceptions.py
index b8c4915a..9d499f9e 100644
--- a/rest/python/server/exceptions.py
+++ b/rest/python/server/exceptions.py
@@ -143,7 +143,7 @@ def __init__(
     self,
     message: str,
     code: str = "VERSION_INVALID_FORMAT",
-    status_code: int = 400,
+    status_code: int = 422,
     severity: ErrorSeverity = ErrorSeverity.UNRECOVERABLE,
   ):
     """Initialize UcpVersionError."""
diff --git a/rest/python/server/integration_test.py b/rest/python/server/integration_test.py
index 3b2d7e98..9181d045 100644
--- a/rest/python/server/integration_test.py
+++ b/rest/python/server/integration_test.py
@@ -16,6 +16,7 @@
 
 import asyncio
 from collections.abc import AsyncGenerator
+import datetime
 import json
 from pathlib import Path
 import shutil
@@ -690,6 +691,27 @@ def test_webhook_delivers_the_bare_order_as_body(self) -> None:
     # The event type travels in the header, not the body.
     self.assertEqual(delivered["headers"].get("X-Event-Type"), "order_placed")
 
+    self.assertIn("Webhook-Id", delivered["headers"])
+    uuid_str = delivered["headers"]["Webhook-Id"]
+    try:
+      uuid.UUID(uuid_str)
+    except ValueError:
+      self.fail(f"Webhook-Id {uuid_str} is not a valid UUID")
+
+    self.assertIn("Webhook-Timestamp", delivered["headers"])
+    timestamp_str = delivered["headers"]["Webhook-Timestamp"]
+    try:
+      timestamp = int(timestamp_str)
+    except ValueError:
+      self.fail(f"Webhook-Timestamp {timestamp_str} is not a valid integer")
+
+    now = int(datetime.datetime.now(datetime.timezone.utc).timestamp())
+    self.assertLess(
+      abs(now - timestamp),
+      5,
+      f"Webhook-Timestamp ({timestamp}) should be close to now ({now})",
+    )
+
     body = delivered["json"]
     # The body IS an order: it validates and carries every required field.
     Order.model_validate(body)
@@ -749,7 +771,7 @@ def test_version_invalid_format(self) -> None:
         headers=headers,
         json=payload.model_dump(mode="json", exclude_none=True),
       )
-      self.assertEqual(response.status_code, 400)
+      self.assertEqual(response.status_code, 422)
 
       # Verify the error structure matches UcpErrorResponse
       data = response.json()
diff --git a/rest/python/server/services/checkout_service.py b/rest/python/server/services/checkout_service.py
index f2ed1c53..c3f445ea 100644
--- a/rest/python/server/services/checkout_service.py
+++ b/rest/python/server/services/checkout_service.py
@@ -839,7 +839,13 @@ async def _notify_webhook(self, checkout: Checkout, event_type: str) -> None:
         await client.post(
           webhook_url,
           json=order_data,
-          headers={"X-Event-Type": event_type},
+          headers={
+            "X-Event-Type": event_type,
+            "Webhook-Id": str(uuid.uuid4()),
+            "Webhook-Timestamp": str(
+              int(datetime.datetime.now(datetime.timezone.utc).timestamp())
+            ),
+          },
           timeout=5.0,
         )
     except Exception as e:  # pylint: disable=broad-exception-caught