diff --git a/assets/css/src/components-plugin/_listing.scss b/assets/css/src/components-plugin/_listing.scss
index 877c082a72..229a8c7cbc 100644
--- a/assets/css/src/components-plugin/_listing.scss
+++ b/assets/css/src/components-plugin/_listing.scss
@@ -437,6 +437,10 @@ a.mailpoet-listing-error {
   }
 }
 
+a.mailpoet-listing-link-important {
+  color: $color-secondary !important;
+}
+
 @include respond-to(small-screen) {
   .mailpoet-listing {
     padding: 0;
diff --git a/assets/js/src/segments/dynamic/list.jsx b/assets/js/src/segments/dynamic/list.jsx
index 327011ca09..bc0f63a346 100644
--- a/assets/js/src/segments/dynamic/list.jsx
+++ b/assets/js/src/segments/dynamic/list.jsx
@@ -1,6 +1,7 @@
 import React from 'react';
 import { Link, withRouter } from 'react-router-dom';
 import MailPoet from 'mailpoet';
+import ReactStringReplace from 'react-string-replace';
 import Listing from 'listing/listing.jsx';
 import PropTypes from 'prop-types';
 
@@ -144,7 +145,24 @@ function renderItem(item, actions) {
       { item.is_plugin_missing
         ? (
           <td colSpan="2" className="column mailpoet-hide-on-mobile" data-colname={MailPoet.I18n.t('missingPluginMessageColumn')}>
-            { item.missing_plugin_message }
+            { item.missing_plugin_message
+              && item.missing_plugin_message.message && item.missing_plugin_message.link
+              ? (
+                <>
+                  { ReactStringReplace(
+                    item.missing_plugin_message.message,
+                    /\[link](.*?)\[\/link]/g,
+                    (match) => (
+                      <a className="mailpoet-listing-link-important" key="missingPluginMessageLink" href={item.missing_plugin_message.link} target="_blank" rel="noopener noreferrer">{match}</a>
+                    )
+                  ) }
+                </>
+              )
+              : (
+                <>
+                  { item.missing_plugin_message }
+                </>
+              )}
           </td>
         )
         : (
diff --git a/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php b/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
index e7c3f1fa2f..ec4b645dd9 100644
--- a/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
+++ b/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
@@ -93,10 +93,12 @@ class DynamicSegmentsResponseBuilder {
     if ($missingPlugins) {
       $missingPlugin = reset($missingPlugins);
       $data['is_plugin_missing'] = true;
-      $data['missing_plugin_message'] = sprintf(
-        __('Activate the %s plugin to see the number of subscribers and enable the editing of this segment.', 'mailpoet'),
-        $missingPlugin
-      );
+      $data['missing_plugin_message'] = $this->segmentDependencyValidator->getCustomErrorMessage($missingPlugin)
+        ?:
+        sprintf(
+          __('Activate the %s plugin to see the number of subscribers and enable the editing of this segment.', 'mailpoet'),
+          $missingPlugin
+        );
     } else {
       $data['is_plugin_missing'] = false;
       $data['missing_plugin_message'] = null;
diff --git a/lib/Segments/DynamicSegments/FilterHandler.php b/lib/Segments/DynamicSegments/FilterHandler.php
index 50dbe9e2c6..2f408d484c 100644
--- a/lib/Segments/DynamicSegments/FilterHandler.php
+++ b/lib/Segments/DynamicSegments/FilterHandler.php
@@ -34,6 +34,7 @@ class FilterHandler {
     $filters = $segment->getDynamicFilters();
     $filterSelects = [];
     $subscribersTable = $this->entityManager->getClassMetadata(SubscriberEntity::class)->getTableName();
+    $pluginsForAllFiltersMissing = $this->segmentDependencyValidator->getMissingPluginsByAllFilters($filters);
     foreach ($filters as $filter) {
       $subscribersIdsQuery = $this->entityManager
         ->getConnection()
@@ -41,7 +42,7 @@ class FilterHandler {
         ->select("DISTINCT $subscribersTable.id as inner_subscriber_id")
         ->from($subscribersTable);
       // When a required plugin is missing we want to return empty result
-      if ($this->segmentDependencyValidator->getMissingPluginsByFilter($filter)) {
+      if ($pluginsForAllFiltersMissing || $this->segmentDependencyValidator->getMissingPluginsByFilter($filter)) {
         $subscribersIdsQuery->andWhere('1 = 0');
       } else {
         $this->filterFactory->getFilterForFilterEntity($filter)->apply($subscribersIdsQuery, $filter);
diff --git a/lib/Segments/SegmentDependencyValidator.php b/lib/Segments/SegmentDependencyValidator.php
index 48fecade3b..189b03ed9b 100644
--- a/lib/Segments/SegmentDependencyValidator.php
+++ b/lib/Segments/SegmentDependencyValidator.php
@@ -5,9 +5,16 @@ namespace MailPoet\Segments;
 use MailPoet\Entities\DynamicSegmentFilterData;
 use MailPoet\Entities\DynamicSegmentFilterEntity;
 use MailPoet\Entities\SegmentEntity;
+use MailPoet\Util\License\Features\Subscribers as SubscribersFeature;
 use MailPoet\WP\Functions as WPFunctions;
+use MailPoetVendor\Doctrine\Common\Collections\Collection;
 
 class SegmentDependencyValidator {
+  private const MAILPOET_PREMIUM_PLUGIN = [
+    'id' => 'mailpoet-premium/mailpoet-premium.php',
+    'name' => 'MailPoet Premium',
+  ];
+
   private const WOOCOMMERCE_PLUGIN = [
     'id' => 'woocommerce/woocommerce.php',
     'name' => 'WooCommerce',
@@ -28,12 +35,17 @@ class SegmentDependencyValidator {
     ],
   ];
 
+  /** @var SubscribersFeature */
+  private $subscribersFeature;
+
   /** @var WPFunctions */
   private $wp;
 
   public function __construct(
+    SubscribersFeature $subscribersFeature,
     WPFunctions $wp
   ) {
+    $this->subscribersFeature = $subscribersFeature;
     $this->wp = $wp;
   }
 
@@ -41,8 +53,9 @@ class SegmentDependencyValidator {
    * @return string[]
    */
   public function getMissingPluginsBySegment(SegmentEntity $segment): array {
-    $missingPluginNames = [];
-    foreach ($segment->getDynamicFilters() as $dynamicFilter) {
+    $dynamicFilters = $segment->getDynamicFilters();
+    $missingPluginNames = $this->getMissingPluginsByAllFilters($dynamicFilters);
+    foreach ($dynamicFilters as $dynamicFilter) {
       $missingPlugins = $this->getMissingPluginsByFilter($dynamicFilter);
       if (!$missingPlugins) {
         continue;
@@ -54,6 +67,21 @@ class SegmentDependencyValidator {
     return array_unique($missingPluginNames);
   }
 
+  /**
+   * @param Collection<int, DynamicSegmentFilterEntity> $dynamicFilters
+   */
+  public function getMissingPluginsByAllFilters(Collection $dynamicFilters): array {
+    $missingPluginNames = [];
+    if (count($dynamicFilters) > 1
+      && (!$this->wp->isPluginActive(self::MAILPOET_PREMIUM_PLUGIN['id'])
+        || !$this->subscribersFeature->hasValidPremiumKey()
+        || $this->subscribersFeature->check())
+    ) {
+      $missingPluginNames[] = self::MAILPOET_PREMIUM_PLUGIN['name'];
+    }
+    return $missingPluginNames;
+  }
+
   public function getMissingPluginsByFilter(DynamicSegmentFilterEntity $dynamicSegmentFilter): array {
     $config = $this->getRequiredPluginsConfig($dynamicSegmentFilter->getFilterData()->getFilterType() ?? '');
     return $this->getMissingPlugins($config);
@@ -80,4 +108,17 @@ class SegmentDependencyValidator {
     }
     return $missingPlugins;
   }
+
+  public function getCustomErrorMessage($missingPlugin) {
+    if ($missingPlugin === self::MAILPOET_PREMIUM_PLUGIN['name']
+      && $this->wp->isPluginActive(self::MAILPOET_PREMIUM_PLUGIN['id'])
+      && (!$this->subscribersFeature->hasValidPremiumKey() || $this->subscribersFeature->check())
+    ) {
+      return [
+        'message' => $this->wp->__('Your current MailPoet plan does not support advanced segments. Please [link]upgrade to a MailPoet Premium plan[/link] to reactivate this segment.', 'mailpoet'),
+        'link' => 'https://account.mailpoet.com',
+      ];
+    }
+    return false;
+  }
 }
diff --git a/lib/Util/License/Features/Subscribers.php b/lib/Util/License/Features/Subscribers.php
index f0bc74c943..e2dfebc96f 100644
--- a/lib/Util/License/Features/Subscribers.php
+++ b/lib/Util/License/Features/Subscribers.php
@@ -79,7 +79,7 @@ class Subscribers {
     return $this->hasValidMssKey() && $this->settings->get(self::MSS_SUPPORT_SETTING_KEY) === 'premium';
   }
 
-  private function hasValidPremiumKey() {
+  public function hasValidPremiumKey() {
     $state = $this->settings->get(self::PREMIUM_KEY_STATE);
     return $state === Bridge::KEY_VALID || $state === Bridge::KEY_EXPIRING;
   }