diff --git a/gateway/platforms/webhook.py b/gateway/platforms/webhook.py
index f6080c57dcd..50b59df8948 100644
--- a/gateway/platforms/webhook.py
+++ b/gateway/platforms/webhook.py
@@ -888,9 +888,28 @@ class WebhookAdapter(BasePlatformAdapter):
         # Checked independently of (and before) legacy V1 below — a sender
         # that only ever sends V2 headers must still validate here; nesting
         # this inside `if generic_sig:` would silently skip V2-only senders.
+        #
+        # The presence of X-Webhook-Signature-V2 alone selects V2 mode and
+        # commits to it — it must NOT fall through to the V1 branch just
+        # because the timestamp is missing/malformed/expired. A sender
+        # migrating to V2 typically sends both V1 and V2 headers together
+        # for compatibility; if incomplete V2 fell through to V1, an
+        # attacker who captured one such mixed request could strip the
+        # X-Webhook-Timestamp header from a replay and have it validate
+        # against the still-present, still-unprotected V1 signature instead
+        # — silently downgrading a V2-protected request back to the replay
+        # hole V2 exists to close.
         v2_sig = request.headers.get("X-Webhook-Signature-V2", "")
-        v2_timestamp = request.headers.get("X-Webhook-Timestamp", "")
-        if v2_sig and v2_timestamp:
+        if v2_sig:
+            v2_timestamp = request.headers.get("X-Webhook-Timestamp", "")
+            if not v2_timestamp:
+                logger.warning(
+                    "[webhook] Route '%s' sent X-Webhook-Signature-V2 with "
+                    "no X-Webhook-Timestamp — rejecting rather than "
+                    "falling back to legacy V1",
+                    request.match_info.get("route_name", ""),
+                )
+                return False
             try:
                 ts = int(v2_timestamp)
             except (TypeError, ValueError):
@@ -911,6 +930,8 @@ class WebhookAdapter(BasePlatformAdapter):
         # (deprecated — no replay protection, since the signature only
         # covers the body: a captured (body, signature) pair replays
         # indefinitely with no timestamp binding it to a specific delivery.)
+        # Only reachable when X-Webhook-Signature-V2 was not sent at all —
+        # see the guard above.
         generic_sig = request.headers.get("X-Webhook-Signature", "")
         if generic_sig:
             expected = hmac.new(
diff --git a/tests/gateway/test_webhook_adapter.py b/tests/gateway/test_webhook_adapter.py
index ee5550ba041..a1e235f46e6 100644
--- a/tests/gateway/test_webhook_adapter.py
+++ b/tests/gateway/test_webhook_adapter.py
@@ -277,6 +277,34 @@ class TestValidateSignature:
         })
         assert adapter._validate_signature(req, body, secret) is True
 
+    def test_validate_generic_v2_stripped_timestamp_does_not_downgrade_to_v1(self):
+        """Regression test for a downgrade attack found in review: a sender
+        migrating to V2 typically sends BOTH the V1 and V2 signatures
+        together (for compatibility while both ends update). If an
+        attacker captures one such mixed request and replays it with the
+        X-Webhook-Timestamp header stripped, the presence of
+        X-Webhook-Signature-V2 must still commit to V2 validation and
+        reject — it must NOT silently fall through to validating the
+        still-present, still-unprotected V1 signature instead. Falling
+        through would let an attacker downgrade a V2-protected request
+        back into the exact replay hole V2 exists to close, just by
+        deleting one header from a captured request."""
+        adapter = _make_adapter()
+        body = b'{"event": "push"}'
+        secret = "generic-secret"
+        timestamp = str(int(time.time()))
+        v2_sig = _generic_v2_signature(body, secret, timestamp)
+        v1_sig = _generic_signature(body, secret)
+        # Simulates a captured mixed V1+V2 request replayed with the
+        # timestamp header stripped — V1 signature is still valid on its
+        # own, but must not be reachable via this path.
+        req = _mock_request(headers={
+            "X-Webhook-Signature-V2": v2_sig,
+            "X-Webhook-Signature": v1_sig,
+            # X-Webhook-Timestamp deliberately omitted.
+        })
+        assert adapter._validate_signature(req, body, secret) is False
+
     def test_v1_replay_attack_succeeds_demonstrating_the_hole_v2_closes(self):
         """Regression/documentation test: a captured (body, signature) V1
         pair replays successfully no matter how much time has passed,