diff --git a/contextual_orchestrator/orchestrator.py b/contextual_orchestrator/orchestrator.py
index 47bf590d3..a29afe8a7 100644
--- a/contextual_orchestrator/orchestrator.py
+++ b/contextual_orchestrator/orchestrator.py
@@ -2036,8 +2036,10 @@ def _is_omit_equivalent_control(key: str, value: Any) -> bool:
     return False
 
 
-def _is_request_too_large_error(exc: BaseException) -> bool:
-    """Recognize request-size rejection through a bounded exception chain."""
+def _is_request_too_large_error(
+    exc: BaseException, *, follow_chain: bool = True
+) -> bool:
+    """Recognize a request-size rejection, optionally following its cause chain."""
     current: BaseException | None = exc
     seen: set[int] = set()
     for _ in range(_PROVIDER_ERROR_CHAIN_LIMIT):
@@ -2053,6 +2055,8 @@ def _is_request_too_large_error(exc: BaseException) -> bool:
             )
         ):
             return True
+        if not follow_chain:
+            return False
         if current.__cause__ is not None:
             current = current.__cause__
         elif current.__suppress_context__:
@@ -2068,7 +2072,11 @@ def _is_passthrough_failover_error(
     """Recognize failures proving that a passthrough request was not accepted."""
     if isinstance(exc, _LocalProviderAdmissionTimeout):
         return True
-    if _is_request_too_large_error(exc):
+    if review_free_request and not isinstance(
+        exc, (ProviderUpstreamError, urllib.error.HTTPError)
+    ):
+        return False
+    if _is_request_too_large_error(exc, follow_chain=not review_free_request):
         return True
     current: BaseException | None = exc
     seen: set[int] = set()
@@ -2114,6 +2122,8 @@ def _is_passthrough_failover_error(
             and current.errno == socket.EAI_AGAIN
         ):
             return True
+        if review_free_request:
+            return False
         if current.__cause__ is not None:
             current = current.__cause__
         elif current.__suppress_context__:
@@ -6392,8 +6402,13 @@ def proxy_completion(
                                 )
                         if _is_ambiguous_passthrough_transport_failure(exc) or (
                             review_free_request
-                            and classified.provider_status is None
-                            and classified.retryable
+                            and (
+                                (classified.provider_status is None and classified.retryable)
+                                or (
+                                    not isinstance(exc, (ProviderUpstreamError, urllib.error.HTTPError))
+                                    and (exc.__cause__ is not None or exc.__context__ is not None)
+                                )
+                            )
                         ):
                             # The candidate may already have applied the request.
                             # Review-free completions have no idempotency proof,
diff --git a/tests/test_passthrough_provider_failover.py b/tests/test_passthrough_provider_failover.py
index 99f080984..688de79e9 100644
--- a/tests/test_passthrough_provider_failover.py
+++ b/tests/test_passthrough_provider_failover.py
@@ -395,6 +395,35 @@ def test_free_review_dns_failure_does_not_authorize_replay(wrapped: bool) -> Non
     assert [agent_id for agent_id, _ in client.calls] == ["primary_agent"]
 
 
+@pytest.mark.parametrize("status", [404, 413])
+def test_free_review_wrapped_rejection_does_not_authorize_replay(status: int) -> None:
+    """A prior rejection in an exception chain cannot prove this send was rejected."""
+    body = {"error": {"code": "model_not_found"}} if status == 404 else None
+    with _http_error(status, body) as prior:
+        failure = RuntimeError("synthetic current send outcome unknown")
+        failure.__cause__ = prior
+        client = SequencedProxyClient({
+            "primary_agent": failure,
+            "fallback_agent": {"model": "fallback-model", "choices": []},
+        })
+        orchestrator = _build(client)
+        orchestrator.agents = [
+            replace(agent, tags=(*agent.tags, "cost:free", "review"))
+            for agent in orchestrator.agents
+        ]
+
+        with pytest.raises(ProviderUpstreamError) as caught:
+            orchestrator.proxy_completion({
+                "model": TaskOrchestrator.FREE_MODEL,
+                "messages": [{"role": "user", "content": "synthetic"}],
+            })
+
+    assert (caught.value.client_status, caught.value.error_code, caught.value.retryable) == (
+        502, "provider_outcome_unknown", False,
+    )
+    assert [agent_id for agent_id, _ in client.calls] == ["primary_agent"]
+
+
 def test_virtual_passthrough_keeps_non_size_tool_errors_sticky() -> None:
     """A generic provider invalid_tools response must not hide a bad request."""
     failure = _invalid_tools_error()