diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -2698,6 +2698,7 @@
     'PhabricatorVeryWowEnglishTranslation' => 'infrastructure/internationalization/translation/PhabricatorVeryWowEnglishTranslation.php',
     'PhabricatorViewerDatasource' => 'applications/people/typeahead/PhabricatorViewerDatasource.php',
     'PhabricatorWatcherHasObjectEdgeType' => 'applications/transactions/edges/PhabricatorWatcherHasObjectEdgeType.php',
+    'PhabricatorWebServerSetupCheck' => 'applications/config/check/PhabricatorWebServerSetupCheck.php',
     'PhabricatorWordPressAuthProvider' => 'applications/auth/provider/PhabricatorWordPressAuthProvider.php',
     'PhabricatorWorker' => 'infrastructure/daemon/workers/PhabricatorWorker.php',
     'PhabricatorWorkerActiveTask' => 'infrastructure/daemon/workers/storage/PhabricatorWorkerActiveTask.php',
@@ -6146,6 +6147,7 @@
     'PhabricatorVeryWowEnglishTranslation' => 'PhutilTranslation',
     'PhabricatorViewerDatasource' => 'PhabricatorTypeaheadDatasource',
     'PhabricatorWatcherHasObjectEdgeType' => 'PhabricatorEdgeType',
+    'PhabricatorWebServerSetupCheck' => 'PhabricatorSetupCheck',
     'PhabricatorWordPressAuthProvider' => 'PhabricatorOAuth2AuthProvider',
     'PhabricatorWorkerActiveTask' => 'PhabricatorWorkerTask',
     'PhabricatorWorkerArchiveTask' => 'PhabricatorWorkerTask',
diff --git a/src/applications/config/check/PhabricatorWebServerSetupCheck.php b/src/applications/config/check/PhabricatorWebServerSetupCheck.php
new file mode 100644
--- /dev/null
+++ b/src/applications/config/check/PhabricatorWebServerSetupCheck.php
@@ -0,0 +1,41 @@
+<?php
+
+final class PhabricatorWebServerSetupCheck extends PhabricatorSetupCheck {
+
+  public function getDefaultGroup() {
+    return self::GROUP_OTHER;
+  }
+
+  protected function executeChecks() {
+    $base_uri = PhabricatorEnv::getEnvConfig('phabricator.base-uri');
+    $base_uri = new PhutilURI($base_uri);
+
+    switch ($base_uri->getProtocol()) {
+      case 'http':
+        $future = new HTTPFuture($base_uri->getProtocol().'://127.0.0.1');
+        break;
+
+      case 'https';
+        $future = new HTTPSFuture($base_uri->getProtocol().'://127.0.0.1');
+        break;
+
+      default:
+        return;
+    }
+
+    $future
+      ->addHeader('Host', $base_uri->getDomain())
+      ->addHeader('Accept-Encoding', 'gzip')
+      ->addHeader('Connection', 'Close');
+
+    list($status, $body, $headers) = $future->resolve();
+
+    if (BaseHTTPFuture::getHeader($headers, 'Content-Encoding') != 'gzip') {
+      $this->newIssue('webserver.gzip')
+        ->setName(pht('Enable gzip compression'))
+        ->setMessage(pht('Enable gzip compression.'));
+      return;
+    }
+  }
+
+}