diff --git a/purchase_sale_inter_company/tests/test_inter_company_purchase_sale.py b/purchase_sale_inter_company/tests/test_inter_company_purchase_sale.py
index 45f6b840b3f..cd183b3a956 100644
--- a/purchase_sale_inter_company/tests/test_inter_company_purchase_sale.py
+++ b/purchase_sale_inter_company/tests/test_inter_company_purchase_sale.py
@@ -722,3 +722,32 @@ def test_notify_picking_problem(self):
         self.assertEqual(
             warning_activity.user_id, so_picking_id.company_id.notify_user_id
         )
+
+    def test_raise_picking_problem(self):
+        self.company_a.sync_picking = True
+        self.company_b.sync_picking = True
+        self.company_a.sync_picking_failure_action = "raise"
+        self.company_b.sync_picking_failure_action = "raise"
+
+        purchase = self._create_purchase_order(
+            self.partner_company_b, self.consumable_product
+        )
+        purchase_2 = self._create_purchase_order(
+            self.partner_company_b, self.consumable_product
+        )
+        purchase.order_line += purchase.order_line.copy({"product_qty": 2})
+        sale = self._approve_po(purchase)
+        sale.action_confirm()
+
+        # validate the SO picking
+        so_picking_id = sale.picking_ids
+
+        # Link to a new purchase order so it can trigger
+        # `PO does not exist or has no receipts` in _sync_receipt_with_delivery
+        sale.auto_purchase_order_id = purchase_2
+
+        # Set quantities done on the picking and validate
+        for move in so_picking_id.move_lines:
+            move.quantity_done = move.product_uom_qty
+        with self.assertRaises(UserError):
+            so_picking_id.button_validate()