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
@@ -34,7 +34,9 @@
           ->addRelatedPhabricatorConfig('pygments.enabled')
           ->addPhabricatorConfig('environment.append-paths');
       } else {
-        list($err) = exec_manual('pygmentize -h');
+        list($err, $stdout) = exec_manual('pygmentize -V');
+        $version = array();
+        preg_match('/\D+(\d\.\d\.\d)\D+\d{4}-\d{4}\D+/', $stdout, $version);
         if ($err) {
           $summary = pht(
             'You have enabled pygments and the %s script is '.
@@ -56,6 +58,27 @@
             ->setMessage($message)
             ->addRelatedPhabricatorConfig('pygments.enabled')
             ->addPhabricatorConfig('environment.append-paths');
+        } else {
+            if (version_compare($version[1], '2.0.0', '<')) {
+                $summary = pht(
+                    'You have enabled pygments and the %s script is '.
+                    'available.Upgrading pygmentize to version 2.0 '.
+                    'greater can improve performance in syntax highlighting.');
+
+                $message = pht(
+                    'You may want to upgrade %s. '.
+                    'To upgrade Pygments, visit '.
+                    'pygments.org and follow the '.
+                    'download and install instructions.');
+
+                $this
+                    ->newIssue('pygments.outdated')
+                    ->setName(pht('Outdated %s', 'pygmentize'))
+                    ->setSummary($summary)
+                    ->setMessage($message)
+                    ->addRelatedPhabricatorConfig('pygments.enabled')
+                    ->addPhabricatorConfig('environment.append-paths');
+            }
         }
       }
     } else {