diff --git a/orchestration/tenant_data_sync_orchestrator.py b/orchestration/tenant_data_sync_orchestrator.py
index aa8005bd8..383ca2a98 100644
--- a/orchestration/tenant_data_sync_orchestrator.py
+++ b/orchestration/tenant_data_sync_orchestrator.py
@@ -3,6 +3,7 @@ from typing import Dict, List, Optional, Tuple, Union
 
 from domain.abri.models import AbriRequestRejected, PlaceRef, Tenant
 from etl.hubspot.deal_contacts_client import HubspotDealContactsClient
+from etl.hubspot.errors import HubspotRequestError
 from infrastructure.abri.abri_client import AbriClient
 
 
@@ -106,12 +107,27 @@ class TenantDataSyncOrchestrator:
             return tenancy
 
         contact_ids: List[str] = []
-        for tenant in tenancy.tenants:
-            contact_id = self._hubspot.create_contact(_contact_properties(tenant))
-            self._hubspot.associate_contact_to_deal(
-                deal_id=deal_id, contact_id=contact_id
-            )
-            contact_ids.append(contact_id)
+        associated_ids: List[str] = []
+        for tenant_index, tenant in enumerate(tenancy.tenants):
+            try:
+                contact_id = self._hubspot.create_contact(
+                    _contact_properties(tenant)
+                )
+                contact_ids.append(contact_id)
+                self._hubspot.associate_contact_to_deal(
+                    deal_id=deal_id, contact_id=contact_id
+                )
+                associated_ids.append(contact_id)
+            except HubspotRequestError as error:
+                # Fail fast at the first failed write; `error` is already
+                # scrubbed, so chaining it keeps tracebacks PII-free.
+                raise TenantDataSyncError(
+                    message=str(error),
+                    deal_id=deal_id,
+                    tenant_index=tenant_index,
+                    contact_ids_created=tuple(contact_ids),
+                    contact_ids_associated=tuple(associated_ids),
+                ) from error
 
         return TenantDataSyncSummary(
             tenancy_reference=tenancy.tenancy_reference,