diff --git a/src/applications/config/check/PhabricatorPygmentSetupCheck.php b/src/applications/config/check/PhabricatorPygmentSetupCheck.php
--- a/src/applications/config/check/PhabricatorPygmentSetupCheck.php
+++ b/src/applications/config/check/PhabricatorPygmentSetupCheck.php
@@ -12,8 +12,9 @@
     if ($pygment) {
       if (!Filesystem::binaryExists('pygmentize')) {
         $summary = pht(
-          'You enabled pygments but the %s script is not '.
+          'You enabled %s but the %s script is not '.
           'actually available, your %s is probably broken.',
+          'pygments',
           'pygmentize',
           '$PATH');
 
@@ -21,10 +22,10 @@
           'The environmental variable %s does not contain %s. '.
           'You have enabled pygments, which requires '.
           '%s to be available in your %s variable.',
-          '$PATH',
-          'pygmentize',
-          'pygmentize',
-          '$PATH');
+          phutil_tag('tt', array(), '$PATH'),
+          phutil_tag('tt', array(), 'pygmentize'),
+          phutil_tag('tt', array(), 'pygmentize'),
+          phutil_tag('tt', array(), '$PATH'));
 
         $this
           ->newIssue('pygments.enabled')
@@ -34,11 +35,14 @@
           ->addRelatedPhabricatorConfig('pygments.enabled')
           ->addPhabricatorConfig('environment.append-paths');
       } else {
-        list($err) = exec_manual('pygmentize -h');
+        list($err, $stdout) = exec_manual('pygmentize -V');
+        $version_matches = null;
+        preg_match('/Pygments version (\d(\.\d)+)/', $stdout, $version_matches);
         if ($err) {
           $summary = pht(
-            'You have enabled pygments and the %s script is '.
+            'You have enabled %s and the %s script is '.
             'available, but does not seem to work.',
+            'pygment',
             'pygmentize');
 
           $message = pht(
@@ -47,7 +51,7 @@
             'installed correctly.',
             phutil_tag('tt', array(), 'pygmentize'),
             phutil_tag('tt', array(), '$PATH'),
-            phutil_tag('tt', array(), 'pygmentize -h'));
+            phutil_tag('tt', array(), 'pygmentize -V'));
 
           $this
             ->newIssue('pygments.failed')
@@ -56,7 +60,59 @@
             ->setMessage($message)
             ->addRelatedPhabricatorConfig('pygments.enabled')
             ->addPhabricatorConfig('environment.append-paths');
-        }
+        } else if (empty($version_matches)) {
+          $summary = pht(
+            'You have enabled %s and the %s script is '.
+            'available, but does not seem to output a valid '.
+            'version number.',
+            'pygments',
+            'pygmentize');
+
+          $message = pht(
+            'Phabricator has %s available in %s, but the binary '.
+            'output is not a valid version number when run as %s. '.
+            'Check that it is installed correctly.',
+            phutil_tag('tt', array(), 'pygmentize'),
+            phutil_tag('tt', array(), '$PATH'),
+            phutil_tag('tt', array(), 'pygmentize -V'));
+
+          $this
+            ->newIssue('pygments.invalide')
+            ->setName(pht('%s Invalide Version', 'pygmentize'))
+            ->setSummary($summary)
+            ->setMessage($message)
+            ->addRelatedPhabricatorConfig('pygments.enabled');
+        } else if (version_compare($version_matches[1], '2.0.0', '<')) {
+                $summary = pht(
+                    'You have enabled %s and the %s script is '.
+                    'available. Upgrading %s from version %s '.
+                    'to version %s or greater can improve performance.',
+                    'pygments',
+                    'pygmentize',
+                    'pygments',
+                    $version_matches[1],
+                    '2.0');
+
+                $message = pht(
+                    'You may want to upgrade %s '.
+                    'from version %s to version %s or greater. '.
+                    'To upgrade %s, visit '.
+                    '%s and follow the '.
+                    'upgrade instructions.',
+                    phutil_tag('tt', array(), 'pygments'),
+                    $version_matches[1],
+                    '2.0',
+                    phutil_tag('tt', array(), 'pygments'),
+                    phutil_tag('a', array('href' => 'http://pygments.org'),
+                     'pygments.org'));
+
+                $this
+                    ->newIssue('pygments.outdated')
+                    ->setName(pht('Outdated %s', 'pygmentize'))
+                    ->setSummary($summary)
+                    ->setMessage($message)
+                    ->addRelatedPhabricatorConfig('pygments.enabled');
+            }
       }
     } else {
       $summary = pht(