diff --git a/modules/ppcp-api-client/src/Factory/ShippingPreferenceFactory.php b/modules/ppcp-api-client/src/Factory/ShippingPreferenceFactory.php
index 3c3cee0df..7416560b3 100644
--- a/modules/ppcp-api-client/src/Factory/ShippingPreferenceFactory.php
+++ b/modules/ppcp-api-client/src/Factory/ShippingPreferenceFactory.php
@@ -10,6 +10,9 @@ declare(strict_types=1);
 namespace WooCommerce\PayPalCommerce\ApiClient\Factory;
 
 use WC_Cart;
+use WC_Order;
+use WC_Order_Item_Product;
+use WC_Product;
 use WooCommerce\PayPalCommerce\ApiClient\Entity\ExperienceContext;
 use WooCommerce\PayPalCommerce\ApiClient\Entity\PurchaseUnit;
 
@@ -31,7 +34,8 @@ class ShippingPreferenceFactory {
 		PurchaseUnit $purchase_unit,
 		string $context,
 		?WC_Cart $cart = null,
-		string $funding_source = ''
+		string $funding_source = '',
+		?WC_Order $wc_order = null
 	): string {
 		$contains_physical_goods = $purchase_unit->contains_physical_goods();
 		if ( ! $contains_physical_goods ) {
@@ -39,8 +43,12 @@ class ShippingPreferenceFactory {
 		}
 
 		$has_shipping              = null !== $purchase_unit->shipping();
-		$needs_shipping            = $cart && $cart->needs_shipping();
-		$shipping_address_is_fixed = $needs_shipping && 'checkout' === $context;
+		$needs_shipping            = ( $wc_order && $this->wc_order_needs_shipping( $wc_order ) ) || ( $cart && $cart->needs_shipping() );
+		$shipping_address_is_fixed = $needs_shipping && in_array( $context, array( 'checkout', 'pay-now' ), true );
+
+		if ( ! $needs_shipping ) {
+			return ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING;
+		}
 
 		if ( $shipping_address_is_fixed ) {
 			// Checkout + no address given? Probably something weird happened, like no form validation?
@@ -61,4 +69,26 @@ class ShippingPreferenceFactory {
 
 		return ExperienceContext::SHIPPING_PREFERENCE_GET_FROM_FILE;
 	}
+
+	protected function wc_order_needs_shipping( WC_Order $wc_order ): bool {
+		// WC 9.9.0+.
+		if ( method_exists( $wc_order, 'needs_shipping' ) ) {
+			return $wc_order->needs_shipping();
+		}
+
+		if ( ! wc_shipping_enabled() || wc_get_shipping_method_count( true ) === 0 ) {
+			return false;
+		}
+
+		foreach ( $wc_order->get_items() as $item ) {
+			if ( $item instanceof WC_Order_Item_Product ) {
+				$product = $item->get_product();
+				if ( $product instanceof WC_Product && $product->needs_shipping() ) {
+					return true;
+				}
+			}
+		}
+
+		return false;
+	}
 }
diff --git a/modules/ppcp-button/src/Endpoint/CreateOrderEndpoint.php b/modules/ppcp-button/src/Endpoint/CreateOrderEndpoint.php
index cd8b6c594..ec4ce107d 100644
--- a/modules/ppcp-button/src/Endpoint/CreateOrderEndpoint.php
+++ b/modules/ppcp-button/src/Endpoint/CreateOrderEndpoint.php
@@ -440,7 +440,8 @@ class CreateOrderEndpoint implements EndpointInterface {
 			$this->purchase_unit,
 			$this->parsed_request_data['context'],
 			WC()->cart,
-			$funding_source
+			$funding_source,
+			$wc_order
 		);
 
 		$action = in_array( $this->parsed_request_data['context'], $this->pay_now_contexts, true ) ?
diff --git a/tests/PHPUnit/ApiClient/Factory/ShippingPreferenceFactoryTest.php b/tests/PHPUnit/ApiClient/Factory/ShippingPreferenceFactoryTest.php
index d16dc2dac..99e9f5988 100644
--- a/tests/PHPUnit/ApiClient/Factory/ShippingPreferenceFactoryTest.php
+++ b/tests/PHPUnit/ApiClient/Factory/ShippingPreferenceFactoryTest.php
@@ -5,10 +5,14 @@ namespace WooCommerce\PayPalCommerce\ApiClient\Factory;
 
 use Mockery;
 use WC_Cart;
+use WC_Order;
+use WC_Order_Item_Product;
+use WC_Product;
 use WooCommerce\PayPalCommerce\ApiClient\Entity\ExperienceContext;
 use WooCommerce\PayPalCommerce\ApiClient\Entity\PurchaseUnit;
 use WooCommerce\PayPalCommerce\ApiClient\Entity\Shipping;
 use WooCommerce\PayPalCommerce\TestCase;
+use function Brain\Monkey\Functions\when;
 
 class ShippingPreferenceFactoryTest extends TestCase
 {
@@ -18,6 +22,9 @@ class ShippingPreferenceFactoryTest extends TestCase
 	{
 		parent::setUp();
 
+		when('wc_shipping_enabled')->justReturn(true);
+		when('wc_get_shipping_method_count')->justReturn(2);
+
 		$this->testee = new ShippingPreferenceFactory();
 	}
 
@@ -29,9 +36,10 @@ class ShippingPreferenceFactoryTest extends TestCase
 		string $context,
 		?WC_Cart $cart,
 		string $funding_source,
+		?WC_Order $wc_order,
 		string $expected_result
 	) {
-		$result = $this->testee->from_state($purchase_unit, $context, $cart, $funding_source);
+		$result = $this->testee->from_state($purchase_unit, $context, $cart, $funding_source, $wc_order);
 
 		self::assertEquals($expected_result, $result);
     }
@@ -43,6 +51,7 @@ class ShippingPreferenceFactoryTest extends TestCase
 			'checkout',
 			$this->createCart(true),
 			'',
+			null,
 			ExperienceContext::SHIPPING_PREFERENCE_SET_PROVIDED_ADDRESS,
 		];
 		yield [
@@ -50,6 +59,7 @@ class ShippingPreferenceFactoryTest extends TestCase
 			'checkout',
 			$this->createCart(false),
 			'',
+			null,
 			ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING,
 		];
 		yield [
@@ -57,6 +67,7 @@ class ShippingPreferenceFactoryTest extends TestCase
 			'checkout',
 			$this->createCart(true),
 			'',
+			null,
 			ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING,
 		];
 		yield [
@@ -64,6 +75,7 @@ class ShippingPreferenceFactoryTest extends TestCase
 			'checkout',
 			$this->createCart(true),
 			'card',
+			null,
 			ExperienceContext::SHIPPING_PREFERENCE_SET_PROVIDED_ADDRESS,
 		];
 		yield [
@@ -71,34 +83,39 @@ class ShippingPreferenceFactoryTest extends TestCase
 			'product',
 			null,
 			'',
-			ExperienceContext::SHIPPING_PREFERENCE_GET_FROM_FILE,
+			null,
+			ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING
 		];
 		yield [
 			$this->createPurchaseUnit(true, null),
 			'pay-now',
 			null,
 			'venmo',
-			ExperienceContext::SHIPPING_PREFERENCE_GET_FROM_FILE,
+			$this->createWcOrder(false),
+			ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING
 		];
 		yield [
 			$this->createPurchaseUnit(true, Mockery::mock(Shipping::class)),
 			'pay-now',
 			null,
 			'venmo',
-			ExperienceContext::SHIPPING_PREFERENCE_GET_FROM_FILE,
+			$this->createWcOrder(true),
+			ExperienceContext::SHIPPING_PREFERENCE_SET_PROVIDED_ADDRESS
 		];
 		yield [
 			$this->createPurchaseUnit(true, Mockery::mock(Shipping::class)),
 			'pay-now',
 			null,
 			'card',
-			ExperienceContext::SHIPPING_PREFERENCE_SET_PROVIDED_ADDRESS,
+			$this->createWcOrder(true),
+			ExperienceContext::SHIPPING_PREFERENCE_SET_PROVIDED_ADDRESS
 		];
 		yield [
 			$this->createPurchaseUnit(true, null),
 			'pay-now',
 			null,
 			'card',
+			$this->createWcOrder(false),
 			ExperienceContext::SHIPPING_PREFERENCE_NO_SHIPPING,
 		];
     }
@@ -115,4 +132,16 @@ class ShippingPreferenceFactoryTest extends TestCase
 		$cart->shouldReceive('needs_shipping')->andReturn($needsShipping);
 		return $cart;
 	}
+
+	private function createWcOrder(bool $needsShipping): WC_Order {
+		$product = Mockery::mock(WC_Product::class);
+		$product->shouldReceive('needs_shipping')->andReturn($needsShipping);
+
+		$item = Mockery::mock(WC_Order_Item_Product::class);
+		$item->shouldReceive('get_product')->andReturn($product);
+
+		$wcOrder = Mockery::mock(WC_Order::class);
+		$wcOrder->shouldReceive('get_items')->andReturn([$item]);
+		return $wcOrder;
+	}
 }