diff --git a/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php b/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
index 8145ec30e5..573ed06dd5 100644
--- a/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
+++ b/lib/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilder.php
@@ -51,6 +51,10 @@ class DynamicSegmentsResponseBuilder {
       $filter['id'] = $dynamicFilter->getId();
       $filter['segmentType'] = $dynamicFilter->getFilterData()->getFilterType(); // We need to add filterType with key segmentType due to BC
       $filter['action'] = $dynamicFilter->getFilterData()->getAction();
+      if (isset($filter['wordpressRole']) && !is_array($filter['wordpressRole'])) {
+        // new filters are always array, they support multiple values, the old didn't convert old filters to new format
+        $filter['wordpressRole'] = [$filter['wordpressRole']];
+      }
       $filters[] = $filter;
     }
     $data['filters'] = $filters;
diff --git a/lib/Segments/DynamicSegments/Filters/UserRole.php b/lib/Segments/DynamicSegments/Filters/UserRole.php
index 60b69fe9eb..0d0e32193a 100644
--- a/lib/Segments/DynamicSegments/Filters/UserRole.php
+++ b/lib/Segments/DynamicSegments/Filters/UserRole.php
@@ -39,7 +39,7 @@ class UserRole implements Filter {
     }
 
     $subscribersTable = $this->entityManager->getClassMetadata(SubscriberEntity::class)->getTableName();
-    $parameterSuffix = (string)$filter->getId() ?? Security::generateRandomString();
+    $parameterSuffix = ((string)$filter->getId()) . Security::generateRandomString();
     $condition = $this->createCondition($role, $operator, $parameterSuffix);
     $qb = $queryBuilder->join($subscribersTable, $wpdb->users, 'wpusers', "$subscribersTable.wp_user_id = wpusers.id")
       ->join('wpusers', $wpdb->usermeta, 'wpusermeta', 'wpusers.id = wpusermeta.user_id')
diff --git a/tests/acceptance/Segments/ManageSegmentsCest.php b/tests/acceptance/Segments/ManageSegmentsCest.php
index 3e6686d268..612bf5a0ca 100644
--- a/tests/acceptance/Segments/ManageSegmentsCest.php
+++ b/tests/acceptance/Segments/ManageSegmentsCest.php
@@ -619,6 +619,7 @@ class ManageSegmentsCest {
     $i->fillField(['name' => 'name'], $segmentTitle);
     $i->fillField(['name' => 'description'], $segmentDesc);
     $i->see('WordPress user role', "{$filterRowOne} {$actionSelectElement}");
+    $i->waitForText('Admin', 10, "{$filterRowOne} {$roleSelectElement}");
     $i->see('Admin', "{$filterRowOne} {$roleSelectElement}");
     $i->see('WordPress user role', "{$filterRowTwo} {$actionSelectElement}");
     $i->see('Editor', "{$filterRowTwo} {$roleSelectElement}");
diff --git a/tests/integration/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilderTest.php b/tests/integration/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilderTest.php
index 46725fe40b..62f54304b8 100644
--- a/tests/integration/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilderTest.php
+++ b/tests/integration/API/JSON/ResponseBuilders/DynamicSegmentsResponseBuilderTest.php
@@ -37,7 +37,7 @@ class DynamicSegmentsResponseBuilderTest extends \MailPoetTest {
     expect($response['filters'])->array();
     expect($response['filters'])->count(1);
     expect($response['filters'][0]['segmentType'])->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
-    expect($response['filters'][0]['wordpressRole'])->equals('editor');
+    expect($response['filters'][0]['wordpressRole'])->equals(['editor']);
     expect($response['filters'][0]['action'])->equals(UserRole::TYPE);
   }
 
@@ -64,11 +64,11 @@ class DynamicSegmentsResponseBuilderTest extends \MailPoetTest {
     expect($response['filters'])->array();
     expect($response['filters'])->count(2);
     expect($response['filters'][0]['segmentType'])->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
-    expect($response['filters'][0]['wordpressRole'])->equals('editor');
+    expect($response['filters'][0]['wordpressRole'])->equals(['editor']);
     expect($response['filters'][0]['action'])->equals(UserRole::TYPE);
     expect($response['filters'][0]['connect'])->equals(DynamicSegmentFilterData::CONNECT_TYPE_AND);
     expect($response['filters'][1]['segmentType'])->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
-    expect($response['filters'][1]['wordpressRole'])->equals('administrator');
+    expect($response['filters'][1]['wordpressRole'])->equals(['administrator']);
     expect($response['filters'][1]['action'])->equals(UserRole::TYPE);
     expect($response['filters'][1]['connect'])->equals(DynamicSegmentFilterData::CONNECT_TYPE_AND);
   }
diff --git a/tests/integration/Segments/DynamicSegments/SegmentSaveControllerTest.php b/tests/integration/Segments/DynamicSegments/SegmentSaveControllerTest.php
index ea2bbae5a4..8473e0c2d9 100644
--- a/tests/integration/Segments/DynamicSegments/SegmentSaveControllerTest.php
+++ b/tests/integration/Segments/DynamicSegments/SegmentSaveControllerTest.php
@@ -40,6 +40,7 @@ class SegmentSaveControllerTest extends \MailPoetTest {
     expect($filter->getFilterData()->getAction())->equals(UserRole::TYPE);
     expect($filter->getFilterData()->getData())->equals([
       'wordpressRole' => 'editor',
+      'operator' => DynamicSegmentFilterData::OPERATOR_ANY,
       'connect' => DynamicSegmentFilterData::CONNECT_TYPE_AND,
     ]);
   }
@@ -52,12 +53,12 @@ class SegmentSaveControllerTest extends \MailPoetTest {
       'filters' => [
         [
           'segmentType' => DynamicSegmentFilterData::TYPE_USER_ROLE,
-          'wordpressRole' => 'administrator',
+          'wordpressRole' => ['administrator'],
           'action' => UserRole::TYPE,
         ],
         [
           'segmentType' => DynamicSegmentFilterData::TYPE_USER_ROLE,
-          'wordpressRole' => 'editor',
+          'wordpressRole' => ['editor'],
           'action' => UserRole::TYPE,
         ],
       ],
@@ -73,7 +74,8 @@ class SegmentSaveControllerTest extends \MailPoetTest {
     expect($filter->getFilterData()->getFilterType())->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
     expect($filter->getFilterData()->getAction())->equals(UserRole::TYPE);
     expect($filter->getFilterData()->getData())->equals([
-      'wordpressRole' => 'administrator',
+      'wordpressRole' => ['administrator'],
+      'operator' => DynamicSegmentFilterData::OPERATOR_ANY,
       'connect' => DynamicSegmentFilterData::CONNECT_TYPE_OR,
     ]);
     $filter = $segment->getDynamicFilters()->next();
@@ -81,15 +83,16 @@ class SegmentSaveControllerTest extends \MailPoetTest {
     expect($filter->getFilterData()->getFilterType())->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
     expect($filter->getFilterData()->getAction())->equals(UserRole::TYPE);
     expect($filter->getFilterData()->getData())->equals([
-      'wordpressRole' => 'editor',
+      'wordpressRole' => ['editor'],
+      'operator' => DynamicSegmentFilterData::OPERATOR_ANY,
       'connect' => DynamicSegmentFilterData::CONNECT_TYPE_OR,
     ]);
   }
 
   public function testItCanRemoveRedundantFilter() {
     $segment = $this->createSegment('Test Segment');
-    $this->addDynamicFilter($segment, 'editor');
-    $this->addDynamicFilter($segment, 'administrator');
+    $this->addDynamicFilter($segment, ['editor']);
+    $this->addDynamicFilter($segment, ['administrator']);
     $segmentData = [
       'id' => $segment->getId(),
       'name' => 'Test Segment Edited',
@@ -97,8 +100,9 @@ class SegmentSaveControllerTest extends \MailPoetTest {
       'filters_connect' => DynamicSegmentFilterData::CONNECT_TYPE_OR,
       'filters' => [[
         'segmentType' => DynamicSegmentFilterData::TYPE_USER_ROLE,
-        'wordpressRole' => 'subscriber',
+        'wordpressRole' => ['subscriber'],
         'action' => UserRole::TYPE,
+        'operator' => DynamicSegmentFilterData::OPERATOR_ANY,
         'connect' => DynamicSegmentFilterData::CONNECT_TYPE_OR,
       ]],
     ];
@@ -113,7 +117,8 @@ class SegmentSaveControllerTest extends \MailPoetTest {
     expect($filter->getFilterData()->getFilterType())->equals(DynamicSegmentFilterData::TYPE_USER_ROLE);
     expect($filter->getFilterData()->getAction())->equals(UserRole::TYPE);
     expect($filter->getFilterData()->getData())->equals([
-      'wordpressRole' => 'subscriber',
+      'wordpressRole' => ['subscriber'],
+      'operator' => DynamicSegmentFilterData::OPERATOR_ANY,
       'connect' => DynamicSegmentFilterData::CONNECT_TYPE_OR,
     ]);
   }
@@ -158,7 +163,7 @@ class SegmentSaveControllerTest extends \MailPoetTest {
     return $segment;
   }
 
-  private function addDynamicFilter(SegmentEntity $segment, string $wordpressRole): DynamicSegmentFilterEntity {
+  private function addDynamicFilter(SegmentEntity $segment, array $wordpressRole): DynamicSegmentFilterEntity {
     $filterData = new DynamicSegmentFilterData(DynamicSegmentFilterData::TYPE_USER_ROLE, UserRole::TYPE, [
       'wordpressRole' => $wordpressRole,
       'connect' => DynamicSegmentFilterData::CONNECT_TYPE_AND,