diff --git a/tests/orchestration/test_tenant_data_sync_orchestrator.py b/tests/orchestration/test_tenant_data_sync_orchestrator.py
index 92dd4a885..6fd48e8ea 100644
--- a/tests/orchestration/test_tenant_data_sync_orchestrator.py
+++ b/tests/orchestration/test_tenant_data_sync_orchestrator.py
@@ -499,3 +499,32 @@ def test_run_fails_fast_when_association_fails_and_reports_the_orphaned_contact(
     assert "corr-abc-123" in str(error)  # scrubbed diagnostics carried through
     assert "Solecka" not in rendered_traceback
     assert "09261195827" not in rendered_traceback
+
+
+def test_run_retries_a_rate_limited_hubspot_call_before_succeeding(
+    orchestrator: TenantDataSyncOrchestrator,
+    mock_session: MagicMock,
+    sdk_client: MagicMock,
+) -> None:
+    # Arrange
+    mock_session.post.return_value.content = _tenancy_response(
+        '<Tenant forenames="Amanjeet" main-contact="yes" person_title="Mrs"'
+        ' surname="Okello">1368473</Tenant>'
+    )
+    rate_limited = ContactsApiException(status=429, reason="Too Many Requests")
+    rate_limited.headers = {"x-hubspot-ratelimit-interval-milliseconds": "0"}
+    sdk_client.crm.contacts.basic_api.create.side_effect = [
+        rate_limited,
+        MagicMock(id="60123"),
+    ]
+
+    # Act
+    result = orchestrator.run(PLACE_REF, deal_id=DEAL_ID)
+
+    # Assert
+    assert result == TenantDataSyncSummary(
+        tenancy_reference="10042020051017",
+        contact_ids=("60123",),
+        vulnerable_contact_count=0,
+    )
+    assert sdk_client.crm.contacts.basic_api.create.call_count == 2