diff --git a/mailpoet/lib/Newsletter/Scheduler/AutomaticEmailScheduler.php b/mailpoet/lib/Newsletter/Scheduler/AutomaticEmailScheduler.php
index 4b81110d08..af5b307136 100644
--- a/mailpoet/lib/Newsletter/Scheduler/AutomaticEmailScheduler.php
+++ b/mailpoet/lib/Newsletter/Scheduler/AutomaticEmailScheduler.php
@@ -122,8 +122,15 @@ class AutomaticEmailScheduler {
       // try to find existing scheduled task for given subscriber
       $task = $this->scheduledTasksRepository->findOneScheduledByNewsletterAndSubscriber($newsletter, $subscriber);
       if ($task) {
-        $this->sendingQueuesRepository->deleteByTask($task);
+        $queue = $task->getSendingQueue();
+        if ($queue instanceof SendingQueueEntity) {
+          $this->sendingQueuesRepository->remove($queue);
+        }
         $this->scheduledTaskSubscribersRepository->deleteByTask($task);
+        // In case any of task associated SchedulesTaskSubscriberEntity was loaded we need to detach them
+        foreach ($task->getSubscribers() as $taskSubscriber) {
+          $this->scheduledTaskSubscribersRepository->detach($taskSubscriber);
+        }
         $this->scheduledTasksRepository->remove($task);
         $this->scheduledTasksRepository->flush();
       }
diff --git a/mailpoet/tests/integration/AutomaticEmails/WooCommerce/Events/AbandonedCartTest.php b/mailpoet/tests/integration/AutomaticEmails/WooCommerce/Events/AbandonedCartTest.php
index 7a19cc3f52..812a66ac06 100644
--- a/mailpoet/tests/integration/AutomaticEmails/WooCommerce/Events/AbandonedCartTest.php
+++ b/mailpoet/tests/integration/AutomaticEmails/WooCommerce/Events/AbandonedCartTest.php
@@ -347,6 +347,7 @@ class AbandonedCartTest extends \MailPoetTest {
     $this->entityManager->flush();
 
     $scheduledTask->setScheduledAt($scheduleAt);
+    $scheduledTask->setSendingQueue($sendingQueue);
     $scheduledTask->setStatus(($this->currentTime < $scheduleAt) ? ScheduledTaskEntity::STATUS_SCHEDULED : ScheduledTaskEntity::STATUS_COMPLETED);
     $this->entityManager->flush();
 
diff --git a/mailpoet/tests/integration/Newsletter/Scheduler/AutomaticEmailTest.php b/mailpoet/tests/integration/Newsletter/Scheduler/AutomaticEmailTest.php
index 36557cd319..6728d68950 100644
--- a/mailpoet/tests/integration/Newsletter/Scheduler/AutomaticEmailTest.php
+++ b/mailpoet/tests/integration/Newsletter/Scheduler/AutomaticEmailTest.php
@@ -50,16 +50,7 @@ class AutomaticEmailTest extends \MailPoetTest {
     $this->scheduledTasksRepository = $this->diContainer->get(ScheduledTasksRepository::class);
 
     $this->newsletterFactory = new NewsletterFactory();
-    $this->newsletter = $this->newsletterFactory->withActiveStatus()->withAutomaticType()->create();
-    $this->newsletterOptionFactory = new NewsletterOptionFactory();
-    $this->newsletterOptionFactory->createMultipleOptions(
-      $this->newsletter,
-      [
-        'sendTo' => 'user',
-        'afterTimeType' => 'hours',
-        'afterTimeNumber' => 2,
-      ]
-    );
+    $this->newsletter = $this->createAutomaticNewsletter();
   }
 
   public function testItCreatesScheduledAutomaticEmailSendingTaskForUser() {
@@ -149,6 +140,30 @@ class AutomaticEmailTest extends \MailPoetTest {
     $this->assertCount(0, $this->sendingQueuesRepository->findAll());
   }
 
+  public function testItCanCancelMultipleAutomaticEmails() {
+    $newsletter = $this->newslettersRepository->findOneById($this->newsletter->getId());
+    $this->newsletterOptionFactory->createMultipleOptions(
+      $this->newsletter,
+      [
+        'group' => 'some_group',
+        'event' => 'some_event',
+      ]
+    );
+    $newsletter2 = $this->createAutomaticNewsletter();
+    $this->newsletterOptionFactory->createMultipleOptions(
+      $newsletter2,
+      [
+        'group' => 'some_group',
+        'event' => 'some_event',
+      ]
+    );
+    $this->assertInstanceOf(NewsletterEntity::class, $newsletter);
+    $subscriber = (new SubscriberFactory())->create();
+    $this->automaticEmailScheduler->createAutomaticEmailScheduledTask($newsletter, $subscriber);
+    $this->automaticEmailScheduler->createAutomaticEmailScheduledTask($newsletter2, $subscriber);
+    $this->automaticEmailScheduler->cancelAutomaticEmail('some_group', 'some_event', $subscriber);
+  }
+
   public function testItSchedulesAutomaticEmailWhenConditionMatches() {
     $currentTime = Carbon::createFromTimestamp(WPFunctions::get()->currentTime('timestamp'));
     $this->newsletterOptionFactory->createMultipleOptions(
@@ -200,6 +215,20 @@ class AutomaticEmailTest extends \MailPoetTest {
       ->equals($currentTime->addHours(2)->format('Y-m-d H:i'));
   }
 
+  private function createAutomaticNewsletter(): NewsletterEntity {
+    $newsletter = $this->newsletterFactory->withActiveStatus()->withAutomaticType()->create();
+    $this->newsletterOptionFactory = new NewsletterOptionFactory();
+    $this->newsletterOptionFactory->createMultipleOptions(
+      $newsletter,
+      [
+        'sendTo' => 'user',
+        'afterTimeType' => 'hours',
+        'afterTimeNumber' => 2,
+      ]
+    );
+    return $newsletter;
+  }
+
   public function _after() {
     Carbon::setTestNow();
     $this->truncateEntity(NewsletterEntity::class);