diff --git a/src/include/abstracts/class-wc-retailcrm-abstracts-settings.php b/src/include/abstracts/class-wc-retailcrm-abstracts-settings.php
index fb85c16..3e21d90 100644
--- a/src/include/abstracts/class-wc-retailcrm-abstracts-settings.php
+++ b/src/include/abstracts/class-wc-retailcrm-abstracts-settings.php
@@ -355,7 +355,7 @@ abstract class WC_Retailcrm_Abstracts_Settings extends WC_Integration
                     }
 
                     $this->form_fields[] = [
-                            'title' => __('Coupon', 'retailcrm'),
+                            'title' => __("Coupon", 'retailcrm'),
                             'type' => 'heading',
                             'description' => '',
                             'id' => 'coupon_options'
diff --git a/src/include/class-wc-retailcrm-history.php b/src/include/class-wc-retailcrm-history.php
index 14cb9b0..0be5dc7 100644
--- a/src/include/class-wc-retailcrm-history.php
+++ b/src/include/class-wc-retailcrm-history.php
@@ -31,6 +31,9 @@ if (!class_exists('WC_Retailcrm_History')) :
         /** @var string */
         protected $bindField = 'externalId';
 
+        /** @var bool */
+        protected $recalculateCoupons = false;
+
         /**
          * WC_Retailcrm_History constructor.
          *
@@ -280,7 +283,7 @@ if (!class_exists('WC_Retailcrm_History')) :
                                     $orderEditData['number'] = $wcOrderNumber;
                                 }
 
-                                $items = $this->updateItemsForUsedCoupons($order, $wcOrder);
+                                $items = $this->updateItemsForUsedCoupons($orderHistory, $wcOrder);
 
                                 if (!empty($items)) {
                                     $orderEditData['items'] = $items;
@@ -467,6 +470,8 @@ if (!class_exists('WC_Retailcrm_History')) :
             }
 
             if (array_key_exists('items', $order)) {
+                $this->recalculateCoupons = true;
+
                 foreach ($order['items'] as $key => $crmProduct) {
                     if (!isset($crmProduct['offer'][$this->bindField])) {
                         continue;
@@ -1015,47 +1020,72 @@ if (!class_exists('WC_Retailcrm_History')) :
         /**
          * Checks use coupons and updates offers
          *
-         * @param array $order
+         * @param array $orderHistory
          * @param array $wcOrder
          *
          * @return array
          */
-        private function updateItemsForUsedCoupons($order, $wcOrder)
+        private function updateItemsForUsedCoupons($orderHistory, $wcOrder)
         {
             $couponField = apply_filters(
                 'retailcrm_coupon_order',
                 $this->retailcrmSettings['woo_coupon_apply_field'],
-                $order,
+                $orderHistory,
                 $wcOrder
             );
 
-            $isNewCoupon = false;
+            if ($couponField === 'not-upload') {
+                return [];
+            }
 
-            if ($couponField !== 'not-upload' && !empty($order['customFields'][$couponField])) {
-                $masCoupons = explode(';', $order['customFields'][$couponField]);
+            $rewriteItems = false;
+            $wcOrderCoupons = $wcOrder->get_coupon_codes();
 
-                foreach ($masCoupons as $coupon) {
-                    if (!empty($coupon) && !in_array($coupon, $wcOrder->get_coupon_codes())) {
-                        $wcOrder->apply_coupon($coupon);
+            if (!empty($orderHistory['customFields'])
+                && array_key_exists($couponField, $orderHistory['customFields'])
+                && empty($orderHistory['customFields'][$couponField])
+                && !empty($wcOrderCoupons)
+            ) {
+                foreach ($wcOrderCoupons as $code) {
+                    $wcOrder->remove_coupon($code);
 
-                        $isNewCoupon = true;
-                    }
+                    $rewriteItems = true;
+                }
+            }
+
+            if (!empty($orderHistory['customFields'][$couponField])) {
+                $masCoupons = explode('; ', $orderHistory['customFields'][$couponField]);
+
+                foreach (array_diff($masCoupons, $wcOrderCoupons) as $coupon) {
+                    $wcOrder->apply_coupon($coupon);
+
+                    $rewriteItems = true;
                 }
 
-                if ($isNewCoupon) {
-                    $orderItem = new WC_Retailcrm_Order_Item($this->retailcrmSettings);
-                    $orderItems = [];
+                foreach (array_diff($wcOrderCoupons, $masCoupons) as $coupon) {
+                    $wcOrder->remove_coupon($coupon);
 
-                    foreach ($wcOrder->get_items() as $item) {
-                        $orderItems[] = $orderItem->build($item)->getData();
-
-                        $orderItem->resetData();
-                    }
-
-                    return $orderItems;
+                    $rewriteItems = true;
                 }
             }
 
+            if (!$rewriteItems && $this->recalculateCoupons) {
+                $wcOrder->recalculate_coupons();
+            }
+
+            if ($rewriteItems || $this->recalculateCoupons) {
+                $orderItem = new WC_Retailcrm_Order_Item($this->retailcrmSettings);
+                $orderItems = [];
+
+                foreach ($wcOrder->get_items() as $item) {
+                    $orderItems[] = $orderItem->build($item)->getData();
+
+                    $orderItem->resetData();
+                }
+
+                return $orderItems;
+            }
+
             return [];
         }
 
diff --git a/src/include/class-wc-retailcrm-orders.php b/src/include/class-wc-retailcrm-orders.php
index 11c0280..d7261d3 100644
--- a/src/include/class-wc-retailcrm-orders.php
+++ b/src/include/class-wc-retailcrm-orders.php
@@ -438,15 +438,15 @@ if (!class_exists('WC_Retailcrm_Orders')) :
             $couponCustomField = $this->retailcrm_settings['woo_coupon_apply_field'];
 
             if ($couponCustomField !== 'not-upload') {
-                $codeCoupons = '';
+                $codeCoupons = [];
 
                 foreach ($order->get_coupons() as $coupon) {
                     if (!empty($coupon->get_code())) {
-                        $codeCoupons .= $coupon->get_code() . ';';
+                        $codeCoupons[] = $coupon->get_code();
                     }
                 }
 
-                $orderData['customFields'][$couponCustomField] = $codeCoupons;
+                $orderData['customFields'][$couponCustomField] = implode('; ', $codeCoupons);
             }
 
             $this->order = WC_Retailcrm_Plugin::clearArray($orderData);
diff --git a/tests/helpers/class-wc-retailcrm-test-case-helper.php b/tests/helpers/class-wc-retailcrm-test-case-helper.php
index 7b1ebbe..4b46519 100644
--- a/tests/helpers/class-wc-retailcrm-test-case-helper.php
+++ b/tests/helpers/class-wc-retailcrm-test-case-helper.php
@@ -79,6 +79,7 @@ class WC_Retailcrm_Test_Case_Helper extends WC_Unit_Test_Case
             ),
             'product_description' => 'full',
             'stores_for_uploading' => ['woocommerce', 'main'],
+            'woo_coupon_apply_field' => 'testField',
         ];
 
         update_option(WC_Retailcrm_Base::$option_key, $options);
diff --git a/tests/test-wc-retailcrm-orders.php b/tests/test-wc-retailcrm-orders.php
index c1889b6..812a279 100644
--- a/tests/test-wc-retailcrm-orders.php
+++ b/tests/test-wc-retailcrm-orders.php
@@ -120,6 +120,7 @@ class WC_Retailcrm_Orders_Test extends WC_Retailcrm_Test_Case_Helper
             $this->assertEquals($orderData['customFields']['crm_order'], 'test_custom_fields');
             $this->assertEquals($orderData['customerComment'], 'crm_customer_comment_test');
             $this->assertEquals($orderData['delivery']['address']['text'], 'crm_address_text_test');
+            $this->assertEquals($orderData['customFields']['testField'], 'test1;test2;');
         } else {
             $this->assertEquals(null, $order);
         }
@@ -596,6 +597,11 @@ class WC_Retailcrm_Orders_Test extends WC_Retailcrm_Test_Case_Helper
     {
         /** @var WC_Order order */
         $this->order = WC_Helper_Order::create_order(0);
+        $coupon1 = WC_Helper_Coupon::create_coupon('test1');
+        $coupon2 = WC_Helper_Coupon::create_coupon('test2');
+
+        $this->order->apply_coupon($coupon1);
+        $this->order->apply_coupon($coupon2);
 
         foreach ($this->order->get_address('billing') as $prop => $value) {
             if (method_exists($this->order, 'set_shipping_' . $prop)) {