diff --git a/plugins/woocommerce/changelog/fix-41506 b/plugins/woocommerce/changelog/fix-41506
new file mode 100644
index 00000000000..6188f3e27e2
--- /dev/null
+++ b/plugins/woocommerce/changelog/fix-41506
@@ -0,0 +1,4 @@
+Significance: patch
+Type: fix
+
+Fixes an issue where coupon usage is not correctly recorded when HPOS is active.
diff --git a/plugins/woocommerce/includes/data-stores/class-wc-coupon-data-store-cpt.php b/plugins/woocommerce/includes/data-stores/class-wc-coupon-data-store-cpt.php
index d36e547d215..abe9022dfbd 100644
--- a/plugins/woocommerce/includes/data-stores/class-wc-coupon-data-store-cpt.php
+++ b/plugins/woocommerce/includes/data-stores/class-wc-coupon-data-store-cpt.php
@@ -347,6 +347,8 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 		} else {
 			add_post_meta( $coupon->get_id(), '_used_by', strtolower( $used_by ) );
 		}
+
+		$this->refresh_coupon_data( $coupon );
 	}
 
 	/**
@@ -375,6 +377,7 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 			if ( $meta_id ) {
 				delete_metadata_by_mid( 'post', $meta_id );
 				$coupon->set_used_by( (array) get_post_meta( $coupon->get_id(), '_used_by' ) );
+				$this->refresh_coupon_data( $coupon );
 			}
 		}
 
@@ -405,6 +408,8 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 			)
 		);
 
+		$this->refresh_coupon_data( $coupon );
+
 		// Get the latest value direct from the DB, instead of possibly the WP meta cache.
 		return (int) $wpdb->get_var( $wpdb->prepare( "SELECT meta_value FROM $wpdb->postmeta WHERE meta_key = 'usage_count' AND post_id = %d;", $id ) );
 	}
@@ -556,7 +561,7 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 			$result = $wpdb->query( $insert_statement ); // WPCS: unprepared SQL ok.
 			if ( false !== $result ) {
 				// Clear meta cache.
-				wp_cache_delete( WC_Coupon::generate_meta_cache_key( $coupon->get_id(), 'coupons' ), 'coupons' );
+				$this->refresh_coupon_data( $coupon );
 				break;
 			}
 		}
@@ -651,7 +656,7 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 			$result = $wpdb->query( $insert_statement ); // WPCS: unprepared SQL ok.
 			if ( false !== $result ) {
 				// Clear meta cache.
-				wp_cache_delete( WC_Coupon::generate_meta_cache_key( $coupon->get_id(), 'coupons' ), 'coupons' );
+				$this->refresh_coupon_data( $coupon );
 				break;
 			}
 		}
@@ -693,6 +698,18 @@ class WC_Coupon_Data_Store_CPT extends WC_Data_Store_WP implements WC_Coupon_Dat
 		); // WPCS: unprepared SQL ok.
 	}
 
+	/**
+	 * This function clears coupon data from the WP cache after certain operations which, for performance reasons,
+	 * are done via SQL queries.
+	 *
+	 * @param \WC_Coupon $coupon The coupon object.
+	 * @return void
+	 */
+	private function refresh_coupon_data( &$coupon ) {
+		wp_cache_delete( $coupon->get_meta_cache_key(), 'coupons' );
+		wp_cache_delete( $coupon->get_id(), 'post_meta' );
+	}
+
 	/**
 	 * Return a coupon code for a specific ID.
 	 *
diff --git a/plugins/woocommerce/tests/php/src/Internal/DataStores/Orders/OrdersTableDataStoreTests.php b/plugins/woocommerce/tests/php/src/Internal/DataStores/Orders/OrdersTableDataStoreTests.php
index 37210b675f7..f2bd371cc24 100644
--- a/plugins/woocommerce/tests/php/src/Internal/DataStores/Orders/OrdersTableDataStoreTests.php
+++ b/plugins/woocommerce/tests/php/src/Internal/DataStores/Orders/OrdersTableDataStoreTests.php
@@ -3198,4 +3198,45 @@ class OrdersTableDataStoreTests extends HposTestCase {
 		remove_all_actions( 'woocommerce_webhook_process_delivery' );
 		remove_all_actions( 'woocommerce_webhook_should_deliver' );
 	}
+
+	/**
+	 * @testDox Check that functions in the datastore correctly hold and release coupons from the order.
+	 */
+	public function test_datastore_coupon_methods() {
+		$this->toggle_cot_authoritative( true );
+
+		$coupon = new \WC_Coupon();
+		$coupon->set_code( '10off' );
+		$coupon->set_discount_type( 'percent' );
+		$coupon->set_amount( 10.0 );
+		$coupon->set_usage_limit_per_user( 2 );
+		$coupon->save();
+
+		$product = WC_Helper_Product::create_simple_product( true );
+
+		WC()->cart->add_to_cart( $product->get_id(), 1 );
+		WC()->cart->add_discount( $coupon->get_code() );
+
+		$this->assertEquals( 0, $coupon->get_data_store()->get_usage_by_email( $coupon, 'user@woo.test' ) );
+
+		$order_id = WC()->checkout->create_order(
+			array(
+				'billing_email'  => 'user@woo.test',
+				'payment_method' => 'dummy',
+			)
+		);
+
+		$this->assertEquals( 1, $coupon->get_data_store()->get_tentative_usages_for_user( $coupon->get_id(), array( 'user@woo.test' ) ) );
+		$this->assertEquals( 1, $coupon->get_data_store()->get_usage_by_email( $coupon, 'user@woo.test' ) );
+
+		wc_get_order( $order_id )->payment_complete();
+
+		$this->assertEquals( 0, $coupon->get_data_store()->get_tentative_usages_for_user( $coupon->get_id(), array( 'user@woo.test' ) ) );
+		$this->assertEquals( 1, $coupon->get_data_store()->get_usage_by_email( $coupon, 'user@woo.test' ) );
+
+		// Load a fresh copy of the coupon and make sure things look ok.
+		$coupon = new \WC_Coupon( $coupon->get_id() );
+		$this->assertContains( 'user@woo.test', $coupon->get_used_by( 'edit' ) );
+	}
+
 }