diff --git a/tests/orchestration/magic_plan/test_magic_plan_orchestrator.py b/tests/orchestration/magic_plan/test_magic_plan_orchestrator.py
index 4eadebc9..c688008e 100644
--- a/tests/orchestration/magic_plan/test_magic_plan_orchestrator.py
+++ b/tests/orchestration/magic_plan/test_magic_plan_orchestrator.py
@@ -1,6 +1,6 @@
 import json
 from pathlib import Path
-from typing import Optional
+from typing import Any, Optional
 from unittest.mock import ANY, MagicMock, patch
 
 import pytest
@@ -75,24 +75,28 @@ def _make_request(
     )
 
 
-def _patch_db() -> tuple[patch, patch, patch]:  # type: ignore[type-arg]
+def _patch_db() -> tuple[Any, Any, Any]:
     return (
         patch("orchestration.magic_plan_orchestrator.PostgresConfig"),
         patch("orchestration.magic_plan_orchestrator.make_engine"),
-        patch("orchestration.magic_plan_orchestrator.make_session"),
+        patch("orchestration.magic_plan_orchestrator.transactional_session"),
     )
 
 
 # --- no match ---
 
 
-def test_run_raises_when_no_plan_found(mock_client: MagicMock) -> None:
+def test_run_returns_none_when_no_plan_found(mock_client: MagicMock) -> None:
     # Arrange
-    mock_client.get_plans.return_value.plans = []
+    mock_client.get_plans.return_value = []
     service = _make_service(mock_client)
     # Act / Assert
-    with pytest.raises(ValueError, match="No MagicPlan found"):
-        service.run(_make_request(address="99 Nowhere Road London SW1A 1AA"))
+    with patch(
+        "orchestration.magic_plan_orchestrator.find_matching_plan",
+        return_value=None,
+    ):
+        result = service.run(_make_request(address="99 Nowhere Road London SW1A 1AA"))
+    assert result is None
 
 
 # --- match found ---
@@ -258,8 +262,8 @@ def test_run_creates_uploaded_file_record(
         return_value=plan_summary,
     ), patch(
         "orchestration.magic_plan_orchestrator.MagicPlanPostgresRepository"
-    ), p_config, p_engine, p_session as mock_make_session:
-        mock_make_session.return_value = mock_session
+    ), p_config, p_engine, p_session as mock_transactional_session:
+        mock_transactional_session.return_value.__enter__.return_value = mock_session
         # Act
         service.run(request)
     # Assert
@@ -268,16 +272,16 @@ def test_run_creates_uploaded_file_record(
         (obj for obj in added_objects if isinstance(obj, UploadedFile)), None
     )
     assert uploaded_file is not None
-    assert uploaded_file.file_source == FileSourceEnum.MAGIC_PLAN.value
-    assert uploaded_file.file_type == FileTypeEnum.MAGIC_PLAN_JSON.value
-    assert uploaded_file.s3_file_bucket == S3_BUCKET
+    assert FileSourceEnum.MAGIC_PLAN.value == uploaded_file.file_source
+    assert FileTypeEnum.MAGIC_PLAN_JSON.value == uploaded_file.file_type
+    assert S3_BUCKET == uploaded_file.s3_file_bucket
     assert (
-        uploaded_file.s3_file_key
-        == f"documents/uprn/100023336956/magic_plan_{plan_summary.id}.json.gz"
+        f"documents/uprn/100023336956/magic_plan_{plan_summary.id}.json.gz"
+        == uploaded_file.s3_file_key
     )
     assert uploaded_file.s3_upload_timestamp is not None
-    assert uploaded_file.uprn == 100023336956
-    assert uploaded_file.hubspot_deal_id == "deal-789"
+    assert 100023336956 == uploaded_file.uprn
+    assert "deal-789" == uploaded_file.hubspot_deal_id
 
 
 def test_run_passes_flushed_uploaded_file_id_to_save(
@@ -307,8 +311,8 @@ def test_run_passes_flushed_uploaded_file_id_to_save(
     ), patch(
         "orchestration.magic_plan_orchestrator.MagicPlanPostgresRepository",
         return_value=mock_repo,
-    ), p_config, p_engine, p_session as mock_make_session:
-        mock_make_session.return_value = mock_session
+    ), p_config, p_engine, p_session as mock_transactional_session:
+        mock_transactional_session.return_value.__enter__.return_value = mock_session
         # Act
         service.run(_make_request())