diff --git a/CRM/Utils/Check/Component/Cleanurls.php b/CRM/Utils/Check/Component/Cleanurls.php
new file mode 100644
index 000000000000..b3b5293452a5
--- /dev/null
+++ b/CRM/Utils/Check/Component/Cleanurls.php
@@ -0,0 +1,28 @@
+<?php
+/*
+ +--------------------------------------------------------------------+
+ | Copyright CiviCRM LLC. All rights reserved.                        |
+ |                                                                    |
+ | This work is published under the GNU AGPLv3 license with some      |
+ | permitted exceptions and without any warranty. For full license    |
+ | and copyright information, see https://civicrm.org/licensing       |
+ +--------------------------------------------------------------------+
+ */
+
+/**
+ *
+ * @package CRM
+ * @copyright CiviCRM LLC https://civicrm.org/licensing
+ */
+class CRM_Utils_Check_Component_Cleanurls extends CRM_Utils_Check_Component {
+
+  /**
+   * For sites running in WordPress, make sure clean URLs are properly set in settings file.
+   *
+   * @return CRM_Utils_Check_Message[]
+   */
+  public static function checkWpCleanurls() {
+    return CRM_Core_Config::singleton()->userSystem->checkCleanurls();
+  }
+
+}
diff --git a/CRM/Utils/System/Base.php b/CRM/Utils/System/Base.php
index d2e5fa93bbe6..9426bf28adee 100644
--- a/CRM/Utils/System/Base.php
+++ b/CRM/Utils/System/Base.php
@@ -1110,4 +1110,8 @@ public function shouldExitAfterFatal() {
     return TRUE;
   }
 
+  public function checkCleanurls() {
+    return [];
+  }
+
 }
diff --git a/CRM/Utils/System/WordPress.php b/CRM/Utils/System/WordPress.php
index 928814f6d6d2..4a73712e7572 100644
--- a/CRM/Utils/System/WordPress.php
+++ b/CRM/Utils/System/WordPress.php
@@ -1509,4 +1509,108 @@ public function shouldExitAfterFatal() {
     return apply_filters('civicrm_exit_after_fatal', $ret);
   }
 
+  /**
+   * Make sure clean URLs are properly set in settings file.
+   *
+   * @return CRM_Utils_Check_Message[]
+   */
+  public function checkCleanurls() {
+    $config = CRM_Core_Config::singleton();
+    $clean = CIVICRM_CLEANURL;
+
+    if ($clean == 1) {
+      //cleanURLs are enabled in CiviCRM, let's make sure the wordpress permalink settings and cache are actually correct by checking the first active contribution page
+      $contributionPages = \Civi\Api4\ContributionPage::get(FALSE)
+        ->addSelect('id')
+        ->addWhere('is_active', '=', TRUE)
+        ->setLimit(1)
+        ->execute();
+      if (count($contributionPages) > 0) {
+        $activePageId = $contributionPages[0]['id'];
+        $message = self::checkCleanPage('/contribute/transact/?reset=1&id=', $activePageId, $config);
+
+        return $message;
+      }
+      else {
+        //no active contribution pages, we can check an event page. This probably won't ever happen.
+        $eventPages = \Civi\Api4\Event::get(FALSE)
+          ->addSelect('id')
+          ->addWhere('is_active', '=', TRUE)
+          ->setLimit(1)
+          ->execute();
+        if (count($eventPages) > 0) {
+          $activePageId = $eventPages[0]['id'];
+          $message = self::checkCleanPage('/event/info/?reset=1&id=', $activePageId, $config);
+
+          return $message;
+        }
+        else {
+          //If there are no active event or contribution pages, we'll skip this check for now.
+
+          return [];
+        }
+      }
+    }
+    else {
+      //cleanURLs aren't enabled or aren't defined correctly in CiviCRM, admin should check civicrm.settings.php
+      $warning = 'Clean URLs are not enabled correctly in CiviCRM. This can lead to "valid id" errors for users registering for events or making donations. Check civicrm.settings.php and review <a href="https://docs.civicrm.org/sysadmin/en/latest/integration/wordpress/clean-urls/">the documentation</a> for more information.';
+
+      return [
+        new CRM_Utils_Check_Message(
+          __FUNCTION__,
+          $warning,
+          ts('Clean URLs Not Enabled'),
+          \Psr\Log\LogLevel::WARNING,
+          'fa-wordpress'
+        ),
+      ];
+    }
+  }
+
+  private static function checkCleanPage($slug, $id, $config) {
+    $page = $config->userFrameworkBaseURL . $config->wpBasePage . $slug . $id;
+    try {
+      $client = new \GuzzleHttp\Client();
+      $res = $client->head($page);
+      $httpCode = $res->getStatusCode();
+    }
+    catch (Exception $e) {
+      Civi::log()->error("Could not run " . __FUNCTION__ . " on $page. GuzzleHttp\Client returned " . $e->getMessage());
+      return [
+        new CRM_Utils_Check_Message(
+          __FUNCTION__,
+          'Could not load a clean page to check',
+          ts('WordPress Permalinks cache needs to be refreshed '),
+          \Psr\Log\LogLevel::ERROR,
+          'fa-wordpress'
+        ),
+      ];
+    }
+
+    if ($httpCode == 404) {
+      $warning = 'Go to Settings > Permalinks and click "Save".';
+
+      $message = new CRM_Utils_Check_Message(
+        __FUNCTION__,
+        $warning,
+        ts('Wordpress Permalinks cache needs to be refreshed.'),
+        \Psr\Log\LogLevel::WARNING,
+        'fa-wordpress',
+      );
+      $message->addAction(
+        'Open WordPress settings',
+        FALSE,
+        'href',
+        ['path' => get_admin_url(NULL, 'options-permalink.php')],
+        'fa-wordpress',
+      );
+
+      return [$message];
+    }
+
+    //sanity
+    return [];
+
+  }
+
 }