diff --git a/mailpoet/lib/API/JSON/v1/Settings.php b/mailpoet/lib/API/JSON/v1/Settings.php
index 382f1fd545..d225de83d9 100644
--- a/mailpoet/lib/API/JSON/v1/Settings.php
+++ b/mailpoet/lib/API/JSON/v1/Settings.php
@@ -22,6 +22,7 @@ use MailPoet\Settings\SettingsController;
 use MailPoet\Settings\TrackingConfig;
 use MailPoet\Statistics\StatisticsOpensRepository;
 use MailPoet\Subscribers\SubscribersCountsController;
+use MailPoet\Util\Notices\DisabledMailFunctionNotice;
 use MailPoet\WooCommerce\TransactionalEmails;
 use MailPoet\WP\Functions as WPFunctions;
 use MailPoetVendor\Carbon\Carbon;
@@ -147,6 +148,17 @@ class Settings extends APIEndpoint {
         $this->messageController->updateSuccessMessages();
       }
 
+      $sendingMethodSet = $settings['mta']['method'] ?? null;
+      if ($sendingMethodSet === 'PHPMail') {
+        // check for valid mail function
+        $this->settings->set(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, true);
+      } else {
+        // when the user switch to a new sending method
+        // do not display the DisabledMailFunctionNotice
+        $this->settings->set(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, false);
+        $this->settings->set(DisabledMailFunctionNotice::OPTION_NAME, false); // do not display notice
+      }
+
       // Tracking and re-engagement Emails
       $meta['showNotice'] = false;
       if ($oldSettings['tracking'] !== $this->settings->get('tracking')) {
diff --git a/mailpoet/lib/Config/Activator.php b/mailpoet/lib/Config/Activator.php
index ebb339ff5e..e09fd42516 100644
--- a/mailpoet/lib/Config/Activator.php
+++ b/mailpoet/lib/Config/Activator.php
@@ -7,6 +7,7 @@ use MailPoet\Cron\CronTrigger;
 use MailPoet\InvalidStateException;
 use MailPoet\Migrator\Migrator;
 use MailPoet\Settings\SettingsController;
+use MailPoet\Util\Notices\DisabledMailFunctionNotice;
 use MailPoet\WP\Functions as WPFunctions;
 use MailPoetVendor\Doctrine\DBAL\Connection;
 
@@ -81,6 +82,8 @@ class Activator {
 
     $localizer = new Localizer();
     $localizer->forceInstallLanguagePacks($this->wp);
+
+    $this->checkForDisabledMailFunction();
   }
 
   public function deactivate() {
@@ -128,6 +131,15 @@ class Activator {
     }
   }
 
+  private function checkForDisabledMailFunction() {
+    $sendingMethodSet = $this->settings->get('mta.method', false);
+
+    if ($sendingMethodSet === 'PHPMail' || is_bool($sendingMethodSet)) {
+      // check for valid mail function
+      $this->settings->set(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, true);
+    }
+  }
+
   private function deleteAllMailPoetTablesAndData(): void {
     $prefix = Env::$dbPrefix;
     if (!$prefix) {
diff --git a/mailpoet/lib/Util/Notices/DisabledMailFunctionNotice.php b/mailpoet/lib/Util/Notices/DisabledMailFunctionNotice.php
index 4d4c40facf..24835ba59d 100644
--- a/mailpoet/lib/Util/Notices/DisabledMailFunctionNotice.php
+++ b/mailpoet/lib/Util/Notices/DisabledMailFunctionNotice.php
@@ -3,6 +3,7 @@
 namespace MailPoet\Util\Notices;
 
 use MailPoet\Mailer\Mailer;
+use MailPoet\Mailer\MailerFactory;
 use MailPoet\Settings\SettingsController;
 use MailPoet\Util\Helpers;
 use MailPoet\Util\License\Features\Subscribers as SubscribersFeature;
@@ -11,7 +12,9 @@ use MailPoet\WP\Notice;
 
 class DisabledMailFunctionNotice {
 
-  const OPTION_NAME = 'disabled-mail-function';
+  const OPTION_NAME = 'disabled_mail_function_check';
+
+  const QUEUE_DISABLED_MAIL_FUNCTION_CHECK = 'queue_disabled_mail_function_check';
 
   /** @var SettingsController */
   private $settings;
@@ -22,18 +25,25 @@ class DisabledMailFunctionNotice {
   /** @var SubscribersFeature */
   private $subscribersFeature;
 
+  /** @var MailerFactory */
+  private $mailerFactory;
+
+  private $isInQueueForChecking = false;
+
   public function __construct(
     WPFunctions $wp,
     SettingsController $settings,
-    SubscribersFeature $subscribersFeature
+    SubscribersFeature $subscribersFeature,
+    MailerFactory $mailerFactory
   ) {
     $this->settings = $settings;
     $this->wp = $wp;
     $this->subscribersFeature = $subscribersFeature;
+    $this->mailerFactory = $mailerFactory;
   }
 
   public function init($shouldDisplay): ?string {
-    $shouldDisplay = $shouldDisplay && $this->checkRequirements();
+    $shouldDisplay = $shouldDisplay && $this->checkMisConfiguredFunction() && $this->checkRequirements();
     if (!$shouldDisplay) {
       return null;
     }
@@ -42,13 +52,43 @@ class DisabledMailFunctionNotice {
   }
 
   private function checkRequirements(): bool {
+    if ($this->isInQueueForChecking) {
+      $this->settings->set(self::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, false);
+    }
+
     $sendingMethod = $this->settings->get('mta.method', false);
     $isPhpMailSendingMethod = $sendingMethod === Mailer::METHOD_PHPMAIL;
 
+    if (!$isPhpMailSendingMethod) {
+      return false; // fails requirements check
+    }
+
     $functionName = 'mail';
     $isMailFunctionDisabled = $this->isFunctionDisabled($functionName);
 
-    return $isPhpMailSendingMethod && $isMailFunctionDisabled;
+    if ($isMailFunctionDisabled) {
+      $this->settings->set(DisabledMailFunctionNotice::OPTION_NAME, true);
+      return true;
+    }
+
+    $isMailFunctionProperlyConfigured = $this->testMailFunctionIsCorrectlyConfigured();
+
+    return !$isMailFunctionProperlyConfigured;
+  }
+
+  /*
+   * Check MisConfigured Function
+   *
+   * This method will cause this class to only display the notice if the settings option
+   *
+   * disabled_mail_function_check === true
+   * or
+   * queue_disabled_mail_function_check === true
+   *
+   */
+  public function checkMisConfiguredFunction(): bool {
+    $this->isInQueueForChecking = $this->settings->get(self::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, false);
+    return $this->settings->get(self::OPTION_NAME, false) || $this->isInQueueForChecking;
   }
 
   public function isFunctionDisabled(string $function): bool {
@@ -90,4 +130,87 @@ class DisabledMailFunctionNotice {
     $link = $this->wp->escAttr($buttonLink);
     return '<p><a target="_blank" href="' . $link . '" class="button button-primary">' . __('Connect MailPoet', 'mailpoet') . '</a></p>';
   }
+
+  /*
+   * Test Mail Function Is Correctly Configured
+   *
+   * This is a workaround for detecting the user PHP mail() function is Correctly Configured and not disabled by the host
+   */
+  private function testMailFunctionIsCorrectlyConfigured(): bool {
+    if ($this->settings->get(DisabledMailFunctionNotice::OPTION_NAME, false)) {
+      return false; // skip sending mail again
+    }
+
+    $mailBody = 'Yup, it works! You can start blasting away emails to the moon.';
+    $sendTestMailData = [
+      'mailer' => $this->settings->get('mta'),
+      'newsletter' => [
+        'subject' => 'This is a Sending Method Test',
+        'body' => [
+          'html' => "<p>$mailBody</p>",
+          'text' => $mailBody,
+        ],
+      ],
+      'subscriber' => 'blackhole@mailpoet.com',
+    ];
+
+    $sendMailResult = $this->sendTestMail($sendTestMailData);
+
+    if (!$sendMailResult) {
+      // Error with PHP mail() function
+      // keep displaying notice
+      $this->settings->set(DisabledMailFunctionNotice::OPTION_NAME, true);
+    }
+
+    return $sendMailResult;
+  }
+
+  /*
+   * Send Test Mail
+   * used to check for valid PHP mail()
+   *
+   * returns true if valid and okay
+   * else returns false if invalid.
+   *
+   * We determine the mail function is invalid by checking against the Exception error thrown by PHPMailer
+   * error message: Could not instantiate mail function.
+   *
+   * if the error is not equal to error message, we consider it okay.
+   */
+  public function sendTestMail($data = []): bool {
+    try {
+      $mailer = $this->mailerFactory->buildMailer(
+        $data['mailer'] ?? null,
+        $data['sender'] ?? null,
+        $data['reply_to'] ?? null
+      );
+      // report this as 'sending_test' in metadata since this endpoint is only used to test sending methods for now
+      $extraParams = [
+        'meta' => [
+          'email_type' => 'sending_test',
+          'subscriber_status' => 'unknown',
+          'subscriber_source' => 'administrator',
+        ],
+      ];
+      $result = $mailer->send($data['newsletter'], $data['subscriber'], $extraParams);
+
+      if ($result['response'] === false) {
+        $errorMessage = $result['error']->getMessage();
+        return !$this->checkForErrorMessage($errorMessage);
+      }
+
+    } catch (\Exception $e) {
+      $errorMessage = $e->getMessage();
+      return !$this->checkForErrorMessage($errorMessage);
+    }
+
+    return true;
+  }
+
+  private function checkForErrorMessage($errorMessage): bool {
+    $phpmailerError = 'Could not instantiate mail function';
+    $substringIndex = stripos($errorMessage, $phpmailerError);
+
+    return $substringIndex !== false;
+  }
 }
diff --git a/mailpoet/lib/Util/Notices/PermanentNotices.php b/mailpoet/lib/Util/Notices/PermanentNotices.php
index bc255e9604..51338992c9 100644
--- a/mailpoet/lib/Util/Notices/PermanentNotices.php
+++ b/mailpoet/lib/Util/Notices/PermanentNotices.php
@@ -3,6 +3,7 @@
 namespace MailPoet\Util\Notices;
 
 use MailPoet\Config\Menu;
+use MailPoet\Mailer\MailerFactory;
 use MailPoet\Settings\SettingsController;
 use MailPoet\Settings\TrackingConfig;
 use MailPoet\Subscribers\SubscribersRepository;
@@ -52,7 +53,8 @@ class PermanentNotices {
     TrackingConfig $trackingConfig,
     SubscribersRepository $subscribersRepository,
     SettingsController $settings,
-    SubscribersFeature $subscribersFeature
+    SubscribersFeature $subscribersFeature,
+    MailerFactory $mailerFactory
   ) {
     $this->wp = $wp;
     $this->phpVersionWarnings = new PHPVersionWarnings();
@@ -65,7 +67,7 @@ class PermanentNotices {
     $this->emailWithInvalidListNotice = new EmailWithInvalidSegmentNotice($wp);
     $this->changedTrackingNotice = new ChangedTrackingNotice($wp);
     $this->deprecatedFilterNotice = new DeprecatedFilterNotice($wp);
-    $this->disabledMailFunctionNotice = new DisabledMailFunctionNotice($wp, $settings, $subscribersFeature);
+    $this->disabledMailFunctionNotice = new DisabledMailFunctionNotice($wp, $settings, $subscribersFeature, $mailerFactory);
   }
 
   public function init() {
diff --git a/mailpoet/tests/integration/Util/Notices/DisabledMailFunctionNoticeTest.php b/mailpoet/tests/integration/Util/Notices/DisabledMailFunctionNoticeTest.php
index 30e37304ed..8b02fc7722 100644
--- a/mailpoet/tests/integration/Util/Notices/DisabledMailFunctionNoticeTest.php
+++ b/mailpoet/tests/integration/Util/Notices/DisabledMailFunctionNoticeTest.php
@@ -4,6 +4,7 @@ namespace MailPoet\Util\Notices;
 
 use Codeception\Util\Stub;
 use MailPoet\Mailer\Mailer;
+use MailPoet\Mailer\MailerFactory;
 use MailPoet\Settings\SettingsController;
 use MailPoet\Util\License\Features\Subscribers as SubscribersFeature;
 use MailPoet\WP\Functions as WPFunctions;
@@ -21,6 +22,7 @@ class DisabledMailFunctionNoticeTest extends \MailPoetTest
     $this->settings = SettingsController::getInstance();
     $this->wp = new WPFunctions;
     $this->settings->set('mta.method', Mailer::METHOD_PHPMAIL);
+    $this->settings->set(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, true);
     $this->wp->setTransient(SubscribersFeature::SUBSCRIBERS_COUNT_CACHE_KEY, 50, SubscribersFeature::SUBSCRIBERS_COUNT_CACHE_EXPIRATION_MINUTES * 60);
   }
 
@@ -35,9 +37,13 @@ class DisabledMailFunctionNoticeTest extends \MailPoetTest
   }
 
   private function generateNotice($methodOverride = []) {
+    $mailerFactoryMock = $this->createMock(MailerFactory::class);
+    $mailerFactoryMock->method('buildMailer')
+      ->willReturn($this->createMock(Mailer::class));
+
     return Stub::construct(
       DisabledMailFunctionNotice::class,
-      [$this->wp, $this->settings, $this->diContainer->get(SubscribersFeature::class)],
+      [$this->wp, $this->settings, $this->diContainer->get(SubscribersFeature::class), $mailerFactoryMock],
       $methodOverride
     );
   }
@@ -81,4 +87,23 @@ class DisabledMailFunctionNoticeTest extends \MailPoetTest
     expect($result)->equals(false);
   }
 
+  public function testItResetQueueCheck() {
+    $this->settings->set(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, true);
+    $disabledMailFunctionNotice = $this->generateNotice();
+    $notice = $disabledMailFunctionNotice->init(true);
+
+    expect($notice)->equals(null);
+    $status = $this->settings->get(DisabledMailFunctionNotice::QUEUE_DISABLED_MAIL_FUNCTION_CHECK, false);
+    expect($status)->equals(false);
+  }
+
+  public function testItDisplayNoticeWhenMailIsMisConfigured() {
+    $disabledMailFunctionNotice = $this->generateNotice(['sendTestMail' => false]);
+    $notice = $disabledMailFunctionNotice->init(true);
+
+    expect($notice)->stringContainsString('Get ready to send your first campaign');
+
+    $status = $this->settings->get(DisabledMailFunctionNotice::OPTION_NAME, false);
+    expect($status)->equals(true);
+  }
 }