diff --git a/application/clicommands/HealthCommand.php b/application/clicommands/HealthCommand.php
index ea28191d..19e13e49 100644
--- a/application/clicommands/HealthCommand.php
+++ b/application/clicommands/HealthCommand.php
@@ -25,7 +25,7 @@ class HealthCommand extends Command
      * OPTIONS
      *
      *   --check <name>  Run only a specific set of checks
-     *                   valid names: config, sync, import, job
+     *                   valid names: config, sync, import, job, deployment
      *   --db <name>     Use a specific Icinga Web DB resource
      */
     public function checkAction()
diff --git a/doc/60-CLI.md b/doc/60-CLI.md
index 2242fe48..aee7b87c 100644
--- a/doc/60-CLI.md
+++ b/doc/60-CLI.md
@@ -303,12 +303,13 @@ Health Check Plugin
 You can use the Director CLI as an Icinga CheckPlugin and monitor your Director
 Health. This will run all or just one of the following test suites:
 
-| Name     | Description                                                       |
-|----------|-------------------------------------------------------------------|
-| `config` | Configuration, Schema, Migrations, Deployment Endpoint            |
-| `sync`   | All configured Sync Rules (pending changes are not a problem)     |
-| `import` | All configured Import Sources (pending changes are not a problem) |
-| `jobs`   | All configured Jobs (ignores disabled ones)                       |
+| Name         | Description                                                       |
+|--------------|-------------------------------------------------------------------|
+| `config`     | Configuration, Schema, Migrations                                 |
+| `sync`       | All configured Sync Rules (pending changes are not a problem)     |
+| `import`     | All configured Import Sources (pending changes are not a problem) |
+| `jobs`       | All configured Jobs (ignores disabled ones)                       |
+| `deployment` | Deployment Endpoint, last deployment outcome                      |
 
 #### Usage
 
diff --git a/doc/82-Changelog.md b/doc/82-Changelog.md
index b88d741b..a0c66b45 100644
--- a/doc/82-Changelog.md
+++ b/doc/82-Changelog.md
@@ -36,6 +36,10 @@ before switching to a new version.
 * FIX: Caching had an influence on context-specific Custom Variable rendering
   when those variables contained macros (#1257)
 
+### Sync
+* FIX: The fix for #1223 caused a regression and broke Sync for objects without
+  a 'disabled' property (Sets, List members) (#1279)
+
 1.4.1
 -----
 ### Fixed issues
diff --git a/library/Director/Health.php b/library/Director/Health.php
index bf783e9a..f84c8178 100644
--- a/library/Director/Health.php
+++ b/library/Director/Health.php
@@ -3,9 +3,11 @@
 namespace Icinga\Module\Director;
 
 use Icinga\Application\Config;
+use Icinga\Date\DateFormatter;
 use Icinga\Module\Director\CheckPlugin\Check;
 use Icinga\Module\Director\CheckPlugin\CheckResults;
 use Icinga\Module\Director\Db\Migrations;
+use Icinga\Module\Director\Objects\DirectorDeploymentLog;
 use Icinga\Module\Director\Objects\DirectorJob;
 use Icinga\Module\Director\Objects\ImportSource;
 use Icinga\Module\Director\Objects\SyncRule;
@@ -20,10 +22,11 @@ class Health
     protected $dbResourceName;
 
     protected $checks = [
-        'config' => 'checkConfig',
-        'sync'   => 'checkSyncRules',
-        'import' => 'checkImportSources',
-        'jobs'   => 'checkDirectorJobs',
+        'config'     => 'checkConfig',
+        'sync'       => 'checkSyncRules',
+        'import'     => 'checkImportSources',
+        'jobs'       => 'checkDirectorJobs',
+        'deployment' => 'checkDeployments',
     ];
 
     public function setDbResourceName($name)
@@ -58,6 +61,7 @@ class Health
         $checks[] = $this->checkSyncRules();
         $checks[] = $this->checkImportSources();
         $checks[] = $this->checkDirectorJobs();
+        $checks[] = $this->checkDeployments();
 
         return $checks;
     }
@@ -133,22 +137,6 @@ class Health
                     $count
                 ));
             }
-        })->call(function () use ($check, $db) {
-            $check->succeed(sprintf(
-                "Deployment endpoint is '%s'",
-                $db->getDeploymentEndpointName()
-            ));
-        })->call(function () use ($check, $db) {
-            $count = $db->countActivitiesSinceLastDeployedConfig();
-
-            if ($count === 1) {
-                $check->succeed('There is a single un-deployed change');
-            } else {
-                $check->succeed(sprintf(
-                    'There are %d un-deployed changes',
-                    $count
-                ));
-            }
         });
 
         return $check;
@@ -235,4 +223,48 @@ class Health
 
         return $check;
     }
+
+    public function checkDeployments()
+    {
+        $check = new Check('Director Deployments');
+
+        $db = $this->getConnection();
+
+        $check->call(function () use ($check, $db) {
+            $check->succeed(sprintf(
+                "Deployment endpoint is '%s'",
+                $db->getDeploymentEndpointName()
+            ));
+        })->call(function () use ($check, $db) {
+            $count = $db->countActivitiesSinceLastDeployedConfig();
+
+            if ($count === 1) {
+                $check->succeed('There is a single un-deployed change');
+            } else {
+                $check->succeed(sprintf(
+                    'There are %d un-deployed changes',
+                    $count
+                ));
+            }
+        });
+
+        if (! DirectorDeploymentLog::hasDeployments($db)) {
+            $check->warn('Configuration has never been deployed');
+            return $check;
+        }
+
+        $latest = DirectorDeploymentLog::loadLatest($db);
+
+        $ts = $latest->getDeploymentTimestamp();
+        $time = DateFormatter::timeAgo($ts);
+        if ($latest->succeeded()) {
+            $check->succeed('The last Deployment was successful ' . $time);
+        } elseif ($latest->isPending()) {
+            $check->warn('The last Deployment succeeded');
+        } else {
+            $check->error('The last Deployment failed');
+        }
+
+        return $check;
+    }
 }