diff --git a/src/wp-admin/includes/class-wp-site-health.php b/src/wp-admin/includes/class-wp-site-health.php
index d8c097c93d..a42732d277 100644
--- a/src/wp-admin/includes/class-wp-site-health.php
+++ b/src/wp-admin/includes/class-wp-site-health.php
@@ -11,14 +11,17 @@ class WP_Site_Health {
 	private $mysql_min_version_check;
 	private $mysql_rec_version_check;
 
-	public  $is_mariadb                          = false;
+	public $is_mariadb                           = false;
 	private $mysql_server_version                = '';
 	private $health_check_mysql_required_version = '5.5';
 	private $health_check_mysql_rec_version      = '';
 
 	public $schedules;
 	public $crons;
-	public $last_missed_cron = null;
+	public $last_missed_cron     = null;
+	public $last_late_cron       = null;
+	private $timeout_missed_cron = null;
+	private $timeout_late_cron   = null;
 
 	/**
 	 * WP_Site_Health constructor.
@@ -28,6 +31,14 @@ class WP_Site_Health {
 	public function __construct() {
 		$this->prepare_sql_data();
 
+		$this->timeout_late_cron   = 0;
+		$this->timeout_missed_cron = - 5 * MINUTE_IN_SECONDS;
+
+		if ( defined( 'DISABLE_WP_CRON' ) && DISABLE_WP_CRON ) {
+			$this->timeout_late_cron   = - 15 * MINUTE_IN_SECONDS;
+			$this->timeout_missed_cron = - 1 * HOUR_IN_SECONDS;
+		}
+
 		add_filter( 'admin_body_class', array( $this, 'admin_body_class' ) );
 
 		add_action( 'admin_enqueue_scripts', array( $this, 'enqueue_scripts' ) );
@@ -1416,21 +1427,32 @@ class WP_Site_Health {
 					$this->has_missed_cron()->get_error_message()
 				)
 			);
-		} else {
-			if ( $this->has_missed_cron() ) {
-				$result['status'] = 'recommended';
+		} elseif ( $this->has_missed_cron() ) {
+			$result['status'] = 'recommended';
 
-				$result['label'] = __( 'A scheduled event has failed' );
+			$result['label'] = __( 'A scheduled event has failed' );
 
-				$result['description'] = sprintf(
-					'<p>%s</p>',
-					sprintf(
-						/* translators: %s: The name of the failed cron event. */
-						__( 'The scheduled event, %s, failed to run. Your site still works, but this may indicate that scheduling posts or automated updates may not work as intended.' ),
-						$this->last_missed_cron
-					)
-				);
-			}
+			$result['description'] = sprintf(
+				'<p>%s</p>',
+				sprintf(
+					/* translators: %s: The name of the failed cron event. */
+					__( 'The scheduled event, %s, failed to run. Your site still works, but this may indicate that scheduling posts or automated updates may not work as intended.' ),
+					$this->last_missed_cron
+				)
+			);
+		} elseif ( $this->has_late_cron() ) {
+			$result['status'] = 'recommended';
+
+			$result['label'] = __( 'A scheduled event is late' );
+
+			$result['description'] = sprintf(
+				'<p>%s</p>',
+				sprintf(
+					/* translators: %s: The name of the late cron event. */
+					__( 'The scheduled event, %s, is late to run. Your site still works, but this may indicate that scheduling posts or automated updates may not work as intended.' ),
+					$this->last_late_cron
+				)
+			);
 		}
 
 		return $result;
@@ -1926,7 +1948,7 @@ class WP_Site_Health {
 		}
 
 		foreach ( $this->crons as $id => $cron ) {
-			if ( ( $cron->time - time() ) < 0 ) {
+			if ( ( $cron->time - time() ) < $this->timeout_missed_cron ) {
 				$this->last_missed_cron = $cron->hook;
 				return true;
 			}
@@ -1935,6 +1957,33 @@ class WP_Site_Health {
 		return false;
 	}
 
+	/**
+	 * Check if any scheduled tasks are late.
+	 *
+	 * Returns a boolean value of `true` if a scheduled task is late and ends processing. If the list of
+	 * crons is an instance of WP_Error, return the instance instead of a boolean value.
+	 *
+	 * @return bool|WP_Error true if a cron is late, false if it wasn't. WP_Error if the cron is set to that.
+	 */
+	public function has_late_cron() {
+		if ( is_wp_error( $this->crons ) ) {
+			return $this->crons;
+		}
+
+		foreach ( $this->crons as $id => $cron ) {
+			$cron_offset = $cron->time - time();
+			if (
+					$cron_offset >= $this->timeout_missed_cron &&
+					$cron_offset < $this->timeout_late_cron
+				) {
+				$this->last_late_cron = $cron->hook;
+				return true;
+			}
+		}
+
+		return false;
+	}
+
 	/**
 	 * Run a loopback test on our site.
 	 *