diff --git a/application/Espo/Core/Mail/Account/GroupAccount/Hooks/AfterFetch.php b/application/Espo/Core/Mail/Account/GroupAccount/Hooks/AfterFetch.php
index 120d9fa17f..88d0053b47 100644
--- a/application/Espo/Core/Mail/Account/GroupAccount/Hooks/AfterFetch.php
+++ b/application/Espo/Core/Mail/Account/GroupAccount/Hooks/AfterFetch.php
@@ -31,7 +31,6 @@ namespace Espo\Core\Mail\Account\GroupAccount\Hooks;
 
 use Espo\Core\Name\Field;
 use Espo\Core\Name\Link;
-use Laminas\Mail\Message;
 
 use Espo\Core\Mail\Account\GroupAccount\AccountFactory as GroupAccountFactory;
 use Espo\Core\Mail\SenderParams;
@@ -97,7 +96,7 @@ class AfterFetch implements AfterFetchInterface
         }
 
         if ($account->createCase()) {
-            if ($beforeFetchResult->get('isAutoReply')) {
+            if ($beforeFetchResult->get('isAutoSubmitted')) {
                 return;
             }
 
@@ -117,7 +116,10 @@ class AfterFetch implements AfterFetchInterface
         }
 
         if ($account->autoReply()) {
-            if ($beforeFetchResult->get('skipAutoReply')) {
+            if (
+                $beforeFetchResult->get('isAutoSubmitted') ||
+                $beforeFetchResult->get('skipAutoReply')
+            ) {
                 return;
             }
 
diff --git a/application/Espo/Core/Mail/Account/GroupAccount/Hooks/BeforeFetch.php b/application/Espo/Core/Mail/Account/GroupAccount/Hooks/BeforeFetch.php
index 61da506be0..97bfdbbeb4 100644
--- a/application/Espo/Core/Mail/Account/GroupAccount/Hooks/BeforeFetch.php
+++ b/application/Espo/Core/Mail/Account/GroupAccount/Hooks/BeforeFetch.php
@@ -75,7 +75,7 @@ class BeforeFetch implements BeforeFetchInterface
 
         return BeforeFetchResult::create()
             ->with('skipAutoReply', $this->checkMessageCannotBeAutoReplied($message))
-            ->with('isAutoReply', $this->checkMessageIsAutoReply($message));
+            ->with('isAutoSubmitted', $this->checkMessageIsAutoSubmitted($message));
     }
 
     private function processBounced(Message $message): bool
@@ -127,16 +127,23 @@ class BeforeFetch implements BeforeFetchInterface
 
     private function checkMessageIsAutoReply(Message $message): bool
     {
+        if ($this->checkMessageIsAutoSubmitted($message)) {
+            return true;
+        }
+
         return $this->autoReplyDetector->detect($message);
     }
 
     private function checkMessageCannotBeAutoReplied(Message $message): bool
     {
-        if ($message->getHeader('X-Auto-Response-Suppress') === 'AutoReply') {
+        if (
+            $message->getHeader('X-Auto-Response-Suppress') === 'AutoReply' ||
+            $message->getHeader('X-Auto-Response-Suppress') === 'All'
+        ) {
             return true;
         }
 
-        if ($message->getHeader('X-Auto-Response-Suppress') === 'All') {
+        if ($this->checkMessageIsAutoSubmitted($message)) {
             return true;
         }
 
@@ -146,4 +153,14 @@ class BeforeFetch implements BeforeFetchInterface
 
         return false;
     }
+
+    private function checkMessageIsAutoSubmitted(Message $message): bool
+    {
+        if ($this->autoReplyDetector->detect($message)) {
+            return true;
+        }
+
+        return $message->getHeader('Auto-Submitted') &&
+            strtolower($message->getHeader('Auto-Submitted')) !== 'no';
+    }
 }
diff --git a/application/Espo/Core/Mail/Importer/DefaultAutoReplyDetector.php b/application/Espo/Core/Mail/Importer/DefaultAutoReplyDetector.php
index eac8e75cfa..bafd486c6b 100644
--- a/application/Espo/Core/Mail/Importer/DefaultAutoReplyDetector.php
+++ b/application/Espo/Core/Mail/Importer/DefaultAutoReplyDetector.php
@@ -44,8 +44,8 @@ class DefaultAutoReplyDetector implements AutoReplyDetector
         }
 
         if (
-            $message->getHeader('Auto-submitted') &&
-            strtolower($message->getHeader('Auto-submitted')) !== 'no'
+            $message->getHeader('Auto-Submitted') &&
+            strtolower($message->getHeader('Auto-Submitted')) === 'auto-replied'
         ) {
             return true;
         }
diff --git a/application/Espo/Core/Mail/Sender.php b/application/Espo/Core/Mail/Sender.php
index b30d54e7f5..fe41d85148 100644
--- a/application/Espo/Core/Mail/Sender.php
+++ b/application/Espo/Core/Mail/Sender.php
@@ -305,7 +305,7 @@ class Sender
 
         $params = array_merge($this->params, $this->overrideParams);
 
-        $this->applyHeaders($message);
+        $this->applyHeaders($email, $message);
         $this->applyFrom($email, $message, $params);
         $this->addRecipientAddresses($email, $message);
         $this->applyReplyTo($email, $message, $params);
@@ -589,7 +589,7 @@ class Sender
         $message->subject($email->getSubject() ?? '');
     }
 
-    private function applyHeaders(Message $message): void
+    private function applyHeaders(Email $email, Message $message): void
     {
         foreach ($this->headers as $item) {
             $message->getHeaders()->addTextHeader($item[0], $item[1]);
@@ -605,6 +605,10 @@ class Sender
                 $message->getHeaders()->addTextHeader($it->getFieldName(), $it->getFieldValue());
             }
         }
+
+        if ($email->isAutoReply() && !$message->getHeaders()->has('Auto-Submitted')) {
+            $message->getHeaders()->addTextHeader('Auto-Submitted', 'auto-replied');
+        }
     }
 
     private function prepareEnvelope(Message $message): ?Envelope
diff --git a/application/Espo/Modules/Crm/Tools/MassEmail/DefaultMessageHeadersPreparator.php b/application/Espo/Modules/Crm/Tools/MassEmail/DefaultMessageHeadersPreparator.php
index f06a1bec79..829d70c71a 100644
--- a/application/Espo/Modules/Crm/Tools/MassEmail/DefaultMessageHeadersPreparator.php
+++ b/application/Espo/Modules/Crm/Tools/MassEmail/DefaultMessageHeadersPreparator.php
@@ -43,6 +43,7 @@ class DefaultMessageHeadersPreparator implements MessageHeadersPreparator
     {
         $headers->addTextHeader('X-Queue-Item-Id', $data->getId());
         $headers->addTextHeader('Precedence', 'bulk');
+        $headers->addTextHeader('Auto-Submitted', 'auto-generated');
 
         $this->addMandatoryOptOut($headers, $data);
     }
diff --git a/application/Espo/Tools/EmailNotification/Processor.php b/application/Espo/Tools/EmailNotification/Processor.php
index 80394f4e35..59aa90c3c3 100644
--- a/application/Espo/Tools/EmailNotification/Processor.php
+++ b/application/Espo/Tools/EmailNotification/Processor.php
@@ -339,8 +339,7 @@ class Processor
         $subject = $this->getHtmlizer()->render($note, $subjectTpl, 'mention-email-subject', $data, true);
         $body = $this->getHtmlizer()->render($note, $bodyTpl, 'mention-email-body', $data, true);
 
-        /** @var Email $email */
-        $email = $this->entityManager->getNewEntity(Email::ENTITY_TYPE);
+        $email = $this->entityManager->getRDBRepositoryByClass(Email::class)->getNew();
 
         $email
             ->setSubject($subject)
@@ -365,10 +364,15 @@ class Processor
             }
         }
 
+        $sender = $this->emailSender
+            ->withParams($senderParams);
+
+        if ($note->getType() !== Note::TYPE_POST) {
+            $sender = $sender->withAddedHeader('Auto-Submitted', 'auto-generated');
+        }
+
         try {
-            $this->emailSender
-                ->withParams($senderParams)
-                ->send($email);
+            $sender->send($email);
         } catch (Exception $e) {
             $this->log->error("Email notification: {$e->getMessage()}", ['exception' => $e]);
         }
diff --git a/application/Espo/Tools/LeadCapture/ConfirmationSender.php b/application/Espo/Tools/LeadCapture/ConfirmationSender.php
index f96b436dd7..f46a811221 100644
--- a/application/Espo/Tools/LeadCapture/ConfirmationSender.php
+++ b/application/Espo/Tools/LeadCapture/ConfirmationSender.php
@@ -218,6 +218,7 @@ class ConfirmationSender
         }
 
         $sender
+            ->withAddedHeader('Auto-Submitted', 'auto-generated')
             ->withAttachments($emailData->getAttachmentList())
             ->send($email);
     }
diff --git a/application/Espo/Tools/UserSecurity/Password/Sender.php b/application/Espo/Tools/UserSecurity/Password/Sender.php
index 24ea5ca28c..6c20f12d85 100644
--- a/application/Espo/Tools/UserSecurity/Password/Sender.php
+++ b/application/Espo/Tools/UserSecurity/Password/Sender.php
@@ -88,7 +88,9 @@ class Sender
             ->setSubject($subject)
             ->setBody($body);
 
-        $this->createSender()->send($email);
+        $this->createSender()
+            ->withAddedHeader('Auto-Submitted', 'auto-generated')
+            ->send($email);
     }
 
     /**
@@ -127,7 +129,9 @@ class Sender
             ->setBody($body)
             ->addToAddress($emailAddress);
 
-        $this->createSender()->send($email);
+        $this->createSender()
+            ->withAddedHeader('Auto-Submitted', 'auto-generated')
+            ->send($email);
     }
 
     private function createSender(): EmailSenderSender