diff --git a/apps/api/src/services/telegram_gateway.py b/apps/api/src/services/telegram_gateway.py
index cb4e62e3d..3e31688f2 100644
--- a/apps/api/src/services/telegram_gateway.py
+++ b/apps/api/src/services/telegram_gateway.py
@@ -6469,6 +6469,14 @@ class TelegramGateway:
                 if destination_binding:
                     sent_receipt["destination_binding"] = destination_binding
                 return sent_receipt
+            if existing_row.get("send_status") == "pending":
+                return {
+                    "status": "reserved",
+                    "run_id": str(delivery_run_id),
+                    "message_id": str(existing_row["message_id"]),
+                    "durable_reservation_committed": True,
+                    "reused_pending_reservation": True,
+                }
             return {
                 "status": "pending_unknown",
                 "run_id": str(delivery_run_id),
diff --git a/apps/api/tests/test_ansible_verified_closure.py b/apps/api/tests/test_ansible_verified_closure.py
index 7d72d19bd..0f690761b 100644
--- a/apps/api/tests/test_ansible_verified_closure.py
+++ b/apps/api/tests/test_ansible_verified_closure.py
@@ -738,7 +738,7 @@ async def test_projection_stays_open_until_durable_telegram_readback(
 
 
 @pytest.mark.asyncio
-async def test_controlled_result_pending_reservation_never_resends_provider(
+async def test_controlled_result_pending_reservation_retries_provider_send(
     monkeypatch: pytest.MonkeyPatch,
 ) -> None:
     class _Response:
@@ -779,9 +779,11 @@ async def test_controlled_result_pending_reservation_never_resends_provider(
                 "message_id": "00000000-0000-0000-0000-000000000202",
             },
             {
-                "status": "pending_unknown",
+                "status": "reserved",
                 "run_id": "00000000-0000-0000-0000-000000000201",
                 "message_id": "00000000-0000-0000-0000-000000000202",
+                "durable_reservation_committed": True,
+                "reused_pending_reservation": True,
             },
         ]
     )
@@ -806,13 +808,15 @@ async def test_controlled_result_pending_reservation_never_resends_provider(
         _controlled_result_payload(),
     )
 
-    assert client.post_count == 1
+    assert client.post_count == 2
     assert first["_awooop_provider_send_performed"] is True
     assert first["_awooop_outbound_mirror_acknowledged"] is False
-    assert second["ok"] is False
-    assert second["_awooop_provider_send_performed"] is False
-    assert second["_awooop_delivery_status"] == "pending_unknown"
-    finalize.assert_awaited_once()
+    assert second["ok"] is True
+    assert second["_awooop_provider_send_performed"] is True
+    assert second["_awooop_delivery_status"] == (
+        "provider_sent_durable_receipt_pending"
+    )
+    assert finalize.await_count == 2
 
 
 @pytest.mark.asyncio