diff --git a/pysus/management/sync.py b/pysus/management/sync.py
index fa84db25..fda0ccb0 100644
--- a/pysus/management/sync.py
+++ b/pysus/management/sync.py
@@ -454,6 +454,10 @@ async def upload_file(
         columns_conn = columns_adapter.raw_connection()
 
         connections = (central_conn, dataset_conn, columns_conn)
+        # Both are read by the `except` handler below, which runs for
+        # failures raised anywhere in the block — including the ones that
+        # happen before either name is bound.
+        raw_path: Path | None = None
         parquet_file = None
         try:
             with central_conn, dataset_conn, columns_conn:
@@ -576,7 +580,8 @@ def _upload_callback(processed: int, total: int) -> None:
                     conn.close()
                 except Exception:  # noqa
                     pass
-            self._cleanup_local(raw_path)
+            if raw_path is not None:
+                self._cleanup_local(raw_path)
             if parquet_file is not None:
                 self._cleanup_local(parquet_file.path)
             raise exc
diff --git a/pysus/tests/management/test_sync_more.py b/pysus/tests/management/test_sync_more.py
index 70df5ad9..d2c4a48e 100644
--- a/pysus/tests/management/test_sync_more.py
+++ b/pysus/tests/management/test_sync_more.py
@@ -524,6 +524,60 @@ async def test_requires_ducklake(self, engine):
         with pytest.raises(Exception, match="not connected"):
             await engine.upload_file(f)
 
+    @pytest.mark.asyncio
+    async def test_error_before_download_propagates_original(
+        self, engine, tmp_path
+    ):
+        """A failure before ``raw_path`` is bound must not be masked.
+
+        The ``except BaseException`` handler cleans up ``raw_path``. When
+        the failure happens earlier in the block (here, the ALTER TABLE
+        issued by ``_ensure_management_columns``), the name is unbound and
+        the handler itself raised ``UnboundLocalError``, replacing the real
+        cause with a misleading message.
+        """
+        engine._ducklake = self._ducklake()
+
+        writer = self._writer()
+        writer._ensure_management_columns.side_effect = RuntimeError(
+            "alter table blew up"
+        )
+
+        with patch.object(
+            SyncEngine, "writer", new_callable=PropertyMock
+        ) as prop:
+            prop.return_value = writer
+            with pytest.raises(RuntimeError, match="alter table blew up"):
+                await engine.upload_file(_remote_file())
+
+    @pytest.mark.asyncio
+    async def test_error_after_download_cleans_up_raw_file(
+        self, engine, tmp_path
+    ):
+        """A failure after the download must still remove the temp file."""
+        raw_path = tmp_path / "X.dbc"
+        raw_path.write_bytes(b"partial")
+
+        engine._ducklake = self._ducklake()
+        engine._download_raw_with_retry = AsyncMock(return_value=raw_path)
+
+        writer = self._writer()
+        writer.get_file_full.return_value = None
+        with (
+            patch.object(
+                SyncEngine, "writer", new_callable=PropertyMock
+            ) as prop,
+            patch(
+                "pysus.management.sync.sha256_of",
+                side_effect=OSError("read failed"),
+            ),
+        ):
+            prop.return_value = writer
+            with pytest.raises(OSError, match="read failed"):
+                await engine.upload_file(_remote_file())
+
+        assert not raw_path.exists()
+
     @pytest.mark.asyncio
     async def test_skips_when_current(self, engine, tmp_path):
         engine._ducklake = self._ducklake()