diff -Nuar a/vendor/magento/module-checkout/Model/GuestPaymentInformationManagement.php b/vendor/magento/module-checkout/Model/GuestPaymentInformationManagement.php
index 592e87b5c4c..72536b3b47b 100644
--- a/vendor/magento/module-checkout/Model/GuestPaymentInformationManagement.php
+++ b/vendor/magento/module-checkout/Model/GuestPaymentInformationManagement.php
@@ -57,18 +57,12 @@ class GuestPaymentInformationManagement implements \Magento\Checkout\Api\GuestPa
     private $logger;
 
     /**
-     * @var ResourceConnection
-     */
-    private $connectionPool;
-
-    /**
      * @param \Magento\Quote\Api\GuestBillingAddressManagementInterface $billingAddressManagement
      * @param \Magento\Quote\Api\GuestPaymentMethodManagementInterface $paymentMethodManagement
      * @param \Magento\Quote\Api\GuestCartManagementInterface $cartManagement
      * @param \Magento\Checkout\Api\PaymentInformationManagementInterface $paymentInformationManagement
      * @param \Magento\Quote\Model\QuoteIdMaskFactory $quoteIdMaskFactory
      * @param CartRepositoryInterface $cartRepository
-     * @param ResourceConnection $connectionPool
      * @codeCoverageIgnore
      */
     public function __construct(
@@ -77,8 +71,7 @@ class GuestPaymentInformationManagement implements \Magento\Checkout\Api\GuestPa
         \Magento\Quote\Api\GuestCartManagementInterface $cartManagement,
         \Magento\Checkout\Api\PaymentInformationManagementInterface $paymentInformationManagement,
         \Magento\Quote\Model\QuoteIdMaskFactory $quoteIdMaskFactory,
-        CartRepositoryInterface $cartRepository,
-        ResourceConnection $connectionPool = null
+        CartRepositoryInterface $cartRepository
     ) {
         $this->billingAddressManagement = $billingAddressManagement;
         $this->paymentMethodManagement = $paymentMethodManagement;
@@ -86,7 +79,6 @@ class GuestPaymentInformationManagement implements \Magento\Checkout\Api\GuestPa
         $this->paymentInformationManagement = $paymentInformationManagement;
         $this->quoteIdMaskFactory = $quoteIdMaskFactory;
         $this->cartRepository = $cartRepository;
-        $this->connectionPool = $connectionPool ?: ObjectManager::getInstance()->get(ResourceConnection::class);
     }
 
     /**
@@ -98,33 +90,23 @@ class GuestPaymentInformationManagement implements \Magento\Checkout\Api\GuestPa
         \Magento\Quote\Api\Data\PaymentInterface $paymentMethod,
         \Magento\Quote\Api\Data\AddressInterface $billingAddress = null
     ) {
-        $salesConnection = $this->connectionPool->getConnection('sales');
-        $checkoutConnection = $this->connectionPool->getConnection('checkout');
-        $salesConnection->beginTransaction();
-        $checkoutConnection->beginTransaction();
-
+        $this->savePaymentInformation($cartId, $email, $paymentMethod, $billingAddress);
         try {
-            $this->savePaymentInformation($cartId, $email, $paymentMethod, $billingAddress);
-            try {
-                $orderId = $this->cartManagement->placeOrder($cartId);
-            } catch (\Magento\Framework\Exception\LocalizedException $e) {
-                throw new CouldNotSaveException(
-                    __($e->getMessage()),
-                    $e
-                );
-            } catch (\Exception $e) {
-                $this->getLogger()->critical($e);
-                throw new CouldNotSaveException(
-                    __('An error occurred on the server. Please try to place the order again.'),
-                    $e
-                );
-            }
-            $salesConnection->commit();
-            $checkoutConnection->commit();
+            $orderId = $this->cartManagement->placeOrder($cartId);
+        } catch (\Magento\Framework\Exception\LocalizedException $e) {
+            $this->getLogger()->critical(
+                'Placing an order with quote_id ' . $cartId . ' is failed: ' . $e->getMessage()
+            );
+            throw new CouldNotSaveException(
+                __($e->getMessage()),
+                $e
+            );
         } catch (\Exception $e) {
-            $salesConnection->rollBack();
-            $checkoutConnection->rollBack();
-            throw $e;
+            $this->getLogger()->critical($e);
+            throw new CouldNotSaveException(
+                __('An error occurred on the server. Please try to place the order again.'),
+                $e
+            );
         }
 
         return $orderId;
diff -Nuar a/vendor/magento/module-checkout/Model/PaymentInformationManagement.php b/vendor/magento/module-checkout/Model/PaymentInformationManagement.php
index e8ab07db184..cf29da7a13c 100644
--- a/vendor/magento/module-checkout/Model/PaymentInformationManagement.php
+++ b/vendor/magento/module-checkout/Model/PaymentInformationManagement.php
@@ -85,6 +85,9 @@ class PaymentInformationManagement implements \Magento\Checkout\Api\PaymentInfor
         try {
             $orderId = $this->cartManagement->placeOrder($cartId);
         } catch (\Magento\Framework\Exception\LocalizedException $e) {
+            $this->getLogger()->critical(
+                'Placing an order with quote_id ' . $cartId . ' is failed: ' . $e->getMessage()
+            );
             throw new CouldNotSaveException(
                 __($e->getMessage()),
                 $e
diff -Nuar a/vendor/magento/module-sales-rule/Model/Coupon/UpdateCouponUsages.php b/vendor/magento/module-sales-rule/Model/Coupon/UpdateCouponUsages.php
new file mode 100644
index 00000000000..3236c80e1b7
--- /dev/null
+++ b/vendor/magento/module-sales-rule/Model/Coupon/UpdateCouponUsages.php
@@ -0,0 +1,153 @@
+<?php
+/**
+ * Copyright © Magento, Inc. All rights reserved.
+ * See COPYING.txt for license details.
+ */
+declare(strict_types=1);
+
+namespace Magento\SalesRule\Model\Coupon;
+
+use Magento\Sales\Api\Data\OrderInterface;
+use Magento\SalesRule\Model\Coupon;
+use Magento\SalesRule\Model\ResourceModel\Coupon\Usage;
+use Magento\SalesRule\Model\Rule\CustomerFactory;
+use Magento\SalesRule\Model\RuleFactory;
+
+/**
+ * Updates the coupon usages.
+ */
+class UpdateCouponUsages
+{
+    /**
+     * @var RuleFactory
+     */
+    private $ruleFactory;
+
+    /**
+     * @var RuleFactory
+     */
+    private $ruleCustomerFactory;
+
+    /**
+     * @var Coupon
+     */
+    private $coupon;
+
+    /**
+     * @var Usage
+     */
+    private $couponUsage;
+
+    /**
+     * @param RuleFactory $ruleFactory
+     * @param CustomerFactory $ruleCustomerFactory
+     * @param Coupon $coupon
+     * @param Usage $couponUsage
+     */
+    public function __construct(
+        RuleFactory $ruleFactory,
+        CustomerFactory $ruleCustomerFactory,
+        Coupon $coupon,
+        Usage $couponUsage
+    ) {
+        $this->ruleFactory = $ruleFactory;
+        $this->ruleCustomerFactory = $ruleCustomerFactory;
+        $this->coupon = $coupon;
+        $this->couponUsage = $couponUsage;
+    }
+
+    /**
+     * Executes the current command.
+     *
+     * @param OrderInterface $subject
+     * @param bool $increment
+     * @return OrderInterface
+     */
+    public function execute(OrderInterface $subject, bool $increment): OrderInterface
+    {
+        if (!$subject || !$subject->getAppliedRuleIds()) {
+            return $subject;
+        }
+        // lookup rule ids
+        $ruleIds = explode(',', $subject->getAppliedRuleIds());
+        $ruleIds = array_unique($ruleIds);
+        $customerId = (int)$subject->getCustomerId();
+        // use each rule (and apply to customer, if applicable)
+        foreach ($ruleIds as $ruleId) {
+            if (!$ruleId) {
+                continue;
+            }
+            $this->updateRuleUsages($increment, (int)$ruleId, $customerId);
+        }
+        $this->updateCouponUsages($subject, $increment, $customerId);
+
+        return $subject;
+    }
+
+    /**
+     * Update the number of rule usages.
+     *
+     * @param bool $increment
+     * @param int $ruleId
+     * @param int $customerId
+     */
+    private function updateRuleUsages(bool $increment, int $ruleId, int $customerId)
+    {
+        /** @var \Magento\SalesRule\Model\Rule $rule */
+        $rule = $this->ruleFactory->create();
+        $rule->load($ruleId);
+        if ($rule->getId()) {
+            $rule->loadCouponCode();
+            if ($increment || $rule->getTimesUsed() > 0) {
+                $rule->setTimesUsed($rule->getTimesUsed() + ($increment ? 1 : -1));
+                $rule->save();
+            }
+            if ($customerId) {
+                $this->updateCustomerRuleUsages($increment, $ruleId, $customerId);
+            }
+        }
+    }
+
+    /**
+     * Update the number of rule usages per customer.
+     *
+     * @param bool $increment
+     * @param int $ruleId
+     * @param int $customerId
+     */
+    private function updateCustomerRuleUsages(bool $increment, int $ruleId, int $customerId): void
+    {
+        /** @var \Magento\SalesRule\Model\Rule\Customer $ruleCustomer */
+        $ruleCustomer = $this->ruleCustomerFactory->create();
+        $ruleCustomer->loadByCustomerRule($customerId, $ruleId);
+        if ($ruleCustomer->getId()) {
+            if ($increment || $ruleCustomer->getTimesUsed() > 0) {
+                $ruleCustomer->setTimesUsed($ruleCustomer->getTimesUsed() + ($increment ? 1 : -1));
+            }
+        } elseif ($increment) {
+            $ruleCustomer->setCustomerId($customerId)->setRuleId($ruleId)->setTimesUsed(1);
+        }
+        $ruleCustomer->save();
+    }
+
+    /**
+     * Update the number of coupon usages.
+     *
+     * @param OrderInterface $subject
+     * @param bool $increment
+     * @param int $customerId
+     */
+    private function updateCouponUsages(OrderInterface $subject, bool $increment, int $customerId): void
+    {
+        $this->coupon->load($subject->getCouponCode(), 'code');
+        if ($this->coupon->getId()) {
+            if ($increment || $this->coupon->getTimesUsed() > 0) {
+                $this->coupon->setTimesUsed($this->coupon->getTimesUsed() + ($increment ? 1 : -1));
+                $this->coupon->save();
+            }
+            if ($customerId) {
+                $this->couponUsage->updateCustomerCouponTimesUsed($customerId, $this->coupon->getId(), $increment);
+            }
+        }
+    }
+}
diff -Nuar a/vendor/magento/module-sales-rule/Model/ResourceModel/Coupon/Usage.php b/vendor/magento/module-sales-rule/Model/ResourceModel/Coupon/Usage.php
index db32bdbe1e9..39a2f8855e2 100644
--- a/vendor/magento/module-sales-rule/Model/ResourceModel/Coupon/Usage.php
+++ b/vendor/magento/module-sales-rule/Model/ResourceModel/Coupon/Usage.php
@@ -27,9 +27,10 @@ class Usage extends \Magento\Framework\Model\ResourceModel\Db\AbstractDb
      *
      * @param int $customerId
      * @param mixed $couponId
+     * @param bool $increment
      * @return void
      */
-    public function updateCustomerCouponTimesUsed($customerId, $couponId)
+    public function updateCustomerCouponTimesUsed($customerId, $couponId, $increment = true): void
     {
         $connection = $this->getConnection();
         $select = $connection->select();
@@ -44,13 +45,13 @@ class Usage extends \Magento\Framework\Model\ResourceModel\Db\AbstractDb
 
         $timesUsed = $connection->fetchOne($select, [':coupon_id' => $couponId, ':customer_id' => $customerId]);
 
-        if ($timesUsed > 0) {
+        if ($timesUsed !== false) {
             $this->getConnection()->update(
                 $this->getMainTable(),
-                ['times_used' => $timesUsed + 1],
+                ['times_used' => $timesUsed + ($increment ? 1 : -1)],
                 ['coupon_id = ?' => $couponId, 'customer_id = ?' => $customerId]
             );
-        } else {
+        } elseif ($increment) {
             $this->getConnection()->insert(
                 $this->getMainTable(),
                 ['coupon_id' => $couponId, 'customer_id' => $customerId, 'times_used' => 1]
diff -Nuar a/vendor/magento/module-sales-rule/Plugin/CouponUsagesDecrement.php b/vendor/magento/module-sales-rule/Plugin/CouponUsagesDecrement.php
new file mode 100644
index 00000000000..87a7c2ed1bd
--- /dev/null
+++ b/vendor/magento/module-sales-rule/Plugin/CouponUsagesDecrement.php
@@ -0,0 +1,59 @@
+<?php
+/**
+ * Copyright © Magento, Inc. All rights reserved.
+ * See COPYING.txt for license details.
+ */
+declare(strict_types=1);
+
+namespace Magento\SalesRule\Plugin;
+
+use Magento\Sales\Model\OrderRepository;
+use Magento\Sales\Model\Service\OrderService;
+use Magento\SalesRule\Model\Coupon\UpdateCouponUsages;
+
+/**
+ * Decrements number of coupon usages after cancelling order.
+ */
+class CouponUsagesDecrement
+{
+    /**
+     * @var UpdateCouponUsages
+     */
+    private $updateCouponUsages;
+
+    /**
+     * @var OrderRepository
+     */
+    private $orderRepository;
+
+    /**
+     * @param UpdateCouponUsages $updateCouponUsages
+     * @param OrderRepository $orderRepository
+     */
+    public function __construct(
+        UpdateCouponUsages $updateCouponUsages,
+        OrderRepository $orderRepository
+    ) {
+        $this->updateCouponUsages = $updateCouponUsages;
+        $this->orderRepository = $orderRepository;
+    }
+
+    /**
+     * Decrements number of coupon usages after cancelling order.
+     *
+     * @param OrderService $subject
+     * @param bool $result
+     * @param int $orderId
+     * @return bool
+     * @SuppressWarnings(PHPMD.UnusedFormalParameter)
+     */
+    public function afterCancel(OrderService $subject, bool $result, $orderId): bool
+    {
+        $order = $this->orderRepository->get($orderId);
+        if ($result) {
+            $this->updateCouponUsages->execute($order, false);
+        }
+
+        return $result;
+    }
+}
diff -Nuar a/vendor/magento/module-sales-rule/Plugin/CouponUsagesIncrement.php b/vendor/magento/module-sales-rule/Plugin/CouponUsagesIncrement.php
new file mode 100644
index 00000000000..14bbb5fce02
--- /dev/null
+++ b/vendor/magento/module-sales-rule/Plugin/CouponUsagesIncrement.php
@@ -0,0 +1,47 @@
+<?php
+/**
+ * Copyright © Magento, Inc. All rights reserved.
+ * See COPYING.txt for license details.
+ */
+declare(strict_types=1);
+
+namespace Magento\SalesRule\Plugin;
+
+use Magento\Sales\Api\Data\OrderInterface;
+use Magento\Sales\Model\Service\OrderService;
+use Magento\SalesRule\Model\Coupon\UpdateCouponUsages;
+
+/**
+ * Increments number of coupon usages after placing order.
+ */
+class CouponUsagesIncrement
+{
+    /**
+     * @var UpdateCouponUsages
+     */
+    private $updateCouponUsages;
+
+    /**
+     * @param UpdateCouponUsages $updateCouponUsages
+     */
+    public function __construct(
+        UpdateCouponUsages $updateCouponUsages
+    ) {
+        $this->updateCouponUsages = $updateCouponUsages;
+    }
+
+    /**
+     * Increments number of coupon usages after placing order.
+     *
+     * @param OrderService $subject
+     * @param OrderInterface $result
+     * @return OrderInterface
+     * @SuppressWarnings(PHPMD.UnusedFormalParameter)
+     */
+    public function afterPlace(OrderService $subject, OrderInterface $result): OrderInterface
+    {
+        $this->updateCouponUsages->execute($result, true);
+
+        return $result;
+    }
+}
diff -Nuar a/vendor/magento/module-sales-rule/etc/di.xml b/vendor/magento/module-sales-rule/etc/di.xml
index 475d5472abc..9326fc93a82 100644
--- a/vendor/magento/module-sales-rule/etc/di.xml
+++ b/vendor/magento/module-sales-rule/etc/di.xml
@@ -182,7 +182,10 @@
     <type name="Magento\Quote\Model\Cart\CartTotalRepository">
         <plugin name="coupon_label_plugin" type="Magento\SalesRule\Plugin\CartTotalRepository" />
     </type>
-
+    <type name="Magento\Sales\Model\Service\OrderService">
+        <plugin name="coupon_uses_decrement_plugin" type="Magento\SalesRule\Plugin\CouponUsagesDecrement" />
+        <plugin name="coupon_uses_increment_plugin" type="Magento\SalesRule\Plugin\CouponUsagesIncrement" sortOrder="20"/>
+    </type>
     <preference
             for="Magento\SalesRule\Model\Spi\CodeLimitManagerInterface"
             type="Magento\SalesRule\Model\Coupon\CodeLimitManager" />
diff -Nuar a/vendor/magento/module-sales-rule/etc/events.xml b/vendor/magento/module-sales-rule/etc/events.xml
index e6b84502552..fb0f711144e 100644
--- a/vendor/magento/module-sales-rule/etc/events.xml
+++ b/vendor/magento/module-sales-rule/etc/events.xml
@@ -6,9 +6,6 @@
  */
 -->
 <config xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:noNamespaceSchemaLocation="urn:magento:framework:Event/etc/events.xsd">
-    <event name="sales_order_place_after">
-        <observer name="salesrule" instance="Magento\SalesRule\Observer\SalesOrderAfterPlaceObserver" />
-    </event>
     <event name="sales_model_service_quote_submit_before">
         <observer name="salesrule" instance="Magento\SalesRule\Observer\AddSalesRuleNameToOrderObserver" />
     </event>