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
@@ -2720,6 +2720,7 @@
     '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',
@@ -6189,6 +6190,7 @@
     '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 +1,45 @@
+<?php
+
+final class PhabricatorWebServerSetupCheck extends PhabricatorSetupCheck {
+
+  public function getDefaultGroup() {
+    return self::GROUP_OTHER;
+  }
+
+  protected function executeChecks() {
+    $base_uri = PhabricatorEnv::getEnvConfig('phabricator.base-uri');
+    $base_uri = id(new PhutilURI($base_uri))
+      ->setPath('/status/');
+
+    // If `phabricator.base-uri` is not set then we can't really do anything.
+    if (!$base_uri) {
+      return;
+    }
+
+    // Make sure that we don't recursively call the setup check.
+    if (AphrontRequest::getHTTPHeader('X-Phabricator-Setup-Check')) {
+      return;
+    }
+
+    $future = id(new HTTPSFuture($base_uri))
+      ->addHeader('Accept-Encoding', 'gzip')
+      ->addHeader('X-Phabricator-Setup-Check', true)
+      ->setTimeout(5);
+
+    list($status, $body, $headers) = $future->resolve();
+
+    if (BaseHTTPFuture::getHeader($headers, 'Content-Encoding') != 'gzip') {
+      $this->newIssue('webserver.gzip')
+        ->setName(pht('Enable gzip compression'))
+        ->setMessage(
+          pht(
+            'All modern browsers support and automatically negotiate gzip '.
+            'compression for all HTTP requests. Enabling gzip compression '.
+            'can reduce the size of the transferred response by up to 90%%, '.
+            'which can significantly reduce the amount of time to download '.
+            'the resource, reduce data usage for the client, and improve '.
+            'the time to first render of your pages.'));
+    }
+  }
+
+}