From 209750e309899a28b8c3239af779a1c869595399 Mon Sep 17 00:00:00 2001
From: Marek Rzytki <rzytki7@gmail.com>
Date: Fri, 19 Jun 2026 10:34:19 +0200
Subject: [PATCH] Fix shipping adjustment removal to clear shipment reference

---
 .../Component/Core/Model/Adjustment.php       | 10 +++
 .../order_with_shipping_adjustment.yml        | 56 ++++++++++++
 ...OrderShippingAdjustmentDoubleFlushTest.php | 85 +++++++++++++++++++
 .../OrderShippingAdjustmentRemovalTest.php    | 50 +++++++++++
 4 files changed, 201 insertions(+)
 create mode 100644 tests/DataFixtures/ORM/resources/order_with_shipping_adjustment.yml
 create mode 100644 tests/Functional/OrderShippingAdjustmentDoubleFlushTest.php
 create mode 100644 tests/Model/OrderShippingAdjustmentRemovalTest.php

diff --git a/src/Sylius/Component/Core/Model/Adjustment.php b/src/Sylius/Component/Core/Model/Adjustment.php
index 869a23cd01..76a9663017 100644
--- a/src/Sylius/Component/Core/Model/Adjustment.php
+++ b/src/Sylius/Component/Core/Model/Adjustment.php
@@ -13,6 +13,7 @@ declare(strict_types=1);
 
 namespace Sylius\Component\Core\Model;
 
+use Sylius\Component\Order\Model\AdjustableInterface;
 use Sylius\Component\Order\Model\Adjustment as BaseAdjustment;
 
 class Adjustment extends BaseAdjustment implements AdjustmentInterface
@@ -20,6 +21,15 @@ class Adjustment extends BaseAdjustment implements AdjustmentInterface
     /** @var ShipmentInterface|null */
     protected $shipment;
 
+    public function setAdjustable(?AdjustableInterface $adjustable): void
+    {
+        parent::setAdjustable($adjustable);
+
+        if ($adjustable === null && $this->shipment !== null) {
+            $this->setShipment(null);
+        }
+    }
+
     public function getShipment(): ?ShipmentInterface
     {
         return $this->shipment;
diff --git a/tests/DataFixtures/ORM/resources/order_with_shipping_adjustment.yml b/tests/DataFixtures/ORM/resources/order_with_shipping_adjustment.yml
new file mode 100644
index 0000000000..2fc9dd83f1
--- /dev/null
+++ b/tests/DataFixtures/ORM/resources/order_with_shipping_adjustment.yml
@@ -0,0 +1,56 @@
+Sylius\Component\Currency\Model\Currency:
+    currency:
+        code: "EUR"
+
+Sylius\Component\Locale\Model\Locale:
+    locale:
+        code: "en_US"
+
+Sylius\Component\Addressing\Model\Zone:
+    zone:
+        code: "TEST_ZONE"
+        name: "Test Zone"
+        type: "country"
+        scope: "all"
+
+Sylius\Component\Core\Model\Channel:
+    channel:
+        code: "TEST"
+        name: "Test Channel"
+        hostname: "localhost"
+        baseCurrency: "@currency"
+        defaultLocale: "@locale"
+        enabled: true
+        taxCalculationStrategy: "order_items_based"
+        currencies: ["@currency"]
+        locales: ["@locale"]
+
+Sylius\Component\Core\Model\ShippingMethod:
+    shipping_method:
+        code: "TEST_FLAT_RATE"
+        enabled: true
+        calculator: "flat_rate"
+        configuration:
+            TEST:
+                amount: 1000
+        zone: "@zone"
+        channels: ["@channel"]
+
+Sylius\Component\Core\Model\Adjustment:
+    shipping_adjustment:
+        type: "shipping"
+        amount: 1000
+        label: "Shipping"
+
+Sylius\Component\Core\Model\Order:
+    order_with_shipping:
+        currencyCode: "EUR"
+        localeCode: "en_US"
+        channel: "@channel"
+
+Sylius\Component\Core\Model\Shipment:
+    order_shipment:
+        method: "@shipping_method"
+        order: "@order_with_shipping"
+        __calls:
+            - addAdjustment: ["@shipping_adjustment"]
diff --git a/tests/Functional/OrderShippingAdjustmentDoubleFlushTest.php b/tests/Functional/OrderShippingAdjustmentDoubleFlushTest.php
new file mode 100644
index 0000000000..ebaaed4ad3
--- /dev/null
+++ b/tests/Functional/OrderShippingAdjustmentDoubleFlushTest.php
@@ -0,0 +1,85 @@
+<?php
+
+/*
+ * This file is part of the Sylius package.
+ *
+ * (c) Sylius Sp. z o.o.
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+declare(strict_types=1);
+
+namespace Sylius\Tests\Functional;
+
+use Doctrine\ORM\EntityManagerInterface;
+use Fidry\AliceDataFixtures\LoaderInterface;
+use Fidry\AliceDataFixtures\Persistence\PurgeMode;
+use PHPUnit\Framework\Attributes\Test;
+use Sylius\Component\Core\Model\AdjustmentInterface;
+use Sylius\Component\Core\Model\Order;
+use Sylius\Component\Core\Model\Shipment;
+use Symfony\Bundle\FrameworkBundle\Test\KernelTestCase;
+
+/**
+ * Reproduces GitHub issue #16347:
+ * Doctrine error when flush() is called twice after removing shipping adjustments
+ * (e.g. event listener flush + API Platform flush during order complete transition).
+ */
+final class OrderShippingAdjustmentDoubleFlushTest extends KernelTestCase
+{
+    private array $fixtures;
+
+    private EntityManagerInterface $entityManager;
+
+    protected function setUp(): void
+    {
+        self::bootKernel();
+
+        /** @var LoaderInterface $fixtureLoader */
+        $fixtureLoader = self::$kernel->getContainer()->get('fidry_alice_data_fixtures.loader.doctrine');
+
+        $this->fixtures = $fixtureLoader->load(
+            [__DIR__ . '/../DataFixtures/ORM/resources/order_with_shipping_adjustment.yml'],
+            [],
+            [],
+            PurgeMode::createDeleteMode(),
+        );
+
+        $this->entityManager = self::$kernel->getContainer()->get('doctrine.orm.entity_manager');
+    }
+
+    #[Test]
+    public function it_allows_multiple_flushes_after_removing_shipping_adjustment_from_order(): void
+    {
+        /** @var Order $order */
+        $order = $this->fixtures['order_with_shipping'];
+
+        /** @var Shipment $shipment */
+        $shipment = $this->fixtures['order_shipment'];
+
+        $this->assertFalse(
+            $order->getAdjustments(AdjustmentInterface::SHIPPING_ADJUSTMENT)->isEmpty(),
+            'Order should have a shipping adjustment before removal',
+        );
+        $this->assertFalse(
+            $shipment->getAdjustments(AdjustmentInterface::SHIPPING_ADJUSTMENT)->isEmpty(),
+            'Shipment should have a shipping adjustment before removal',
+        );
+
+        $order->removeAdjustmentsRecursively(AdjustmentInterface::SHIPPING_ADJUSTMENT);
+
+        $this->entityManager->flush();
+        $this->entityManager->flush();
+
+        $this->assertTrue(
+            $order->getAdjustments(AdjustmentInterface::SHIPPING_ADJUSTMENT)->isEmpty(),
+            'Order should have no shipping adjustments after removal',
+        );
+        $this->assertTrue(
+            $shipment->getAdjustments(AdjustmentInterface::SHIPPING_ADJUSTMENT)->isEmpty(),
+            'Shipment should have no shipping adjustments after removal',
+        );
+    }
+}
diff --git a/tests/Model/OrderShippingAdjustmentRemovalTest.php b/tests/Model/OrderShippingAdjustmentRemovalTest.php
new file mode 100644
index 0000000000..499781f37b
--- /dev/null
+++ b/tests/Model/OrderShippingAdjustmentRemovalTest.php
@@ -0,0 +1,50 @@
+<?php
+
+/*
+ * This file is part of the Sylius package.
+ *
+ * (c) Sylius Sp. z o.o.
+ *
+ * For the full copyright and license information, please view the LICENSE
+ * file that was distributed with this source code.
+ */
+
+declare(strict_types=1);
+
+namespace Sylius\Tests\Model;
+
+use PHPUnit\Framework\Attributes\Test;
+use PHPUnit\Framework\TestCase;
+use Sylius\Component\Core\Model\Adjustment;
+use Sylius\Component\Core\Model\AdjustmentInterface;
+use Sylius\Component\Core\Model\Order;
+use Sylius\Component\Core\Model\Shipment;
+
+final class OrderShippingAdjustmentRemovalTest extends TestCase
+{
+    #[Test]
+    public function it_clears_shipment_reference_when_shipping_adjustment_is_removed_from_order(): void
+    {
+        $order = new Order();
+        $shipment = new Shipment();
+        $shipment->setOrder($order);
+
+        $adjustment = new Adjustment();
+        $adjustment->setType(AdjustmentInterface::SHIPPING_ADJUSTMENT);
+        $adjustment->setAmount(500);
+
+        $shipment->addAdjustment($adjustment);
+
+        $this->assertSame($order, $adjustment->getAdjustable(), 'Adjustment should be assigned to order after addAdjustment on shipment');
+        $this->assertSame($shipment, $adjustment->getShipment(), 'Adjustment should reference the shipment');
+        $this->assertTrue($order->hasAdjustment($adjustment), 'Order should contain the adjustment');
+        $this->assertTrue($shipment->hasAdjustment($adjustment), 'Shipment should contain the adjustment');
+
+        $order->removeAdjustment($adjustment);
+
+        $this->assertNull($adjustment->getAdjustable(), 'Adjustable reference should be cleared');
+        $this->assertNull($adjustment->getShipment(), 'Shipment reference should be cleared after removal from order');
+        $this->assertFalse($order->hasAdjustment($adjustment), 'Order should not contain the adjustment');
+        $this->assertFalse($shipment->hasAdjustment($adjustment), 'Shipment should not contain the adjustment after removal from order');
+    }
+}