diff --git a/resources/celerity/map.php b/resources/celerity/map.php
index d558032906..434aa5b65a 100644
--- a/resources/celerity/map.php
+++ b/resources/celerity/map.php
@@ -41,7 +41,7 @@ return array(
     'rsrc/css/application/conduit/conduit-api.css' => '7bc725c4',
     'rsrc/css/application/config/config-options.css' => '0ede4c9b',
     'rsrc/css/application/config/config-page.css' => '8798e14f',
-    'rsrc/css/application/config/config-template.css' => '8e6c6fcd',
+    'rsrc/css/application/config/config-template.css' => '8f18fa41',
     'rsrc/css/application/config/setup-issue.css' => 'f794cfc3',
     'rsrc/css/application/config/unhandled-exception.css' => '4c96257a',
     'rsrc/css/application/conpherence/durable-column.css' => '86396117',
@@ -777,7 +777,7 @@ return array(
     'phabricator-dashboard-css' => 'bc6f2127',
     'phabricator-drag-and-drop-file-upload' => '58dea2fa',
     'phabricator-draggable-list' => '5a13c79f',
-    'phabricator-fatal-config-template-css' => '8e6c6fcd',
+    'phabricator-fatal-config-template-css' => '8f18fa41',
     'phabricator-feed-css' => 'ecd4ec57',
     'phabricator-file-upload' => '680ea2c8',
     'phabricator-filetree-view-css' => 'fccf9f82',
diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
index b6591a961c..b3051e2a26 100644
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -2685,6 +2685,7 @@ phutil_register_library_map(array(
     'PhabricatorImageMacroRemarkupRule' => 'applications/macro/markup/PhabricatorImageMacroRemarkupRule.php',
     'PhabricatorImageTransformer' => 'applications/files/PhabricatorImageTransformer.php',
     'PhabricatorImagemagickSetupCheck' => 'applications/config/check/PhabricatorImagemagickSetupCheck.php',
+    'PhabricatorInFlightErrorView' => 'applications/config/view/PhabricatorInFlightErrorView.php',
     'PhabricatorIndexEngine' => 'applications/search/index/PhabricatorIndexEngine.php',
     'PhabricatorIndexEngineExtension' => 'applications/search/index/PhabricatorIndexEngineExtension.php',
     'PhabricatorIndexEngineExtensionModule' => 'applications/search/index/PhabricatorIndexEngineExtensionModule.php',
@@ -7509,6 +7510,7 @@ phutil_register_library_map(array(
     'PhabricatorImageMacroRemarkupRule' => 'PhutilRemarkupRule',
     'PhabricatorImageTransformer' => 'Phobject',
     'PhabricatorImagemagickSetupCheck' => 'PhabricatorSetupCheck',
+    'PhabricatorInFlightErrorView' => 'AphrontView',
     'PhabricatorIndexEngine' => 'Phobject',
     'PhabricatorIndexEngineExtension' => 'Phobject',
     'PhabricatorIndexEngineExtensionModule' => 'PhabricatorConfigModule',
diff --git a/src/applications/config/check/PhabricatorSetupCheck.php b/src/applications/config/check/PhabricatorSetupCheck.php
index ad779ed63f..0c9888cd77 100644
--- a/src/applications/config/check/PhabricatorSetupCheck.php
+++ b/src/applications/config/check/PhabricatorSetupCheck.php
@@ -192,6 +192,21 @@ abstract class PhabricatorSetupCheck extends Phobject {
     }
   }
 
+  /**
+   * Test if we've survived through setup on at least one normal request
+   * without fataling.
+   *
+   * If we've made it through setup without hitting any fatals, we switch
+   * to render a more friendly error page when encountering issues like
+   * database connection failures. This gives users a smoother experience in
+   * the face of intermittent failures.
+   *
+   * @return bool True if we've made it through setup since the last restart.
+   */
+  final public static function isInFlight() {
+    return (self::getOpenSetupIssueKeys() !== null);
+  }
+
   final public static function loadAllChecks() {
     return id(new PhutilClassMapQuery())
       ->setAncestorClass(__CLASS__)
diff --git a/src/applications/config/response/PhabricatorConfigResponse.php b/src/applications/config/response/PhabricatorConfigResponse.php
index d4d2effdf5..588f60255f 100644
--- a/src/applications/config/response/PhabricatorConfigResponse.php
+++ b/src/applications/config/response/PhabricatorConfigResponse.php
@@ -25,11 +25,21 @@ final class PhabricatorConfigResponse extends AphrontStandaloneHTMLResponse {
   }
 
   protected function getResponseBodyClass() {
-    return 'setup-fatal';
+    if (PhabricatorSetupCheck::isInFlight()) {
+      return 'setup-fatal in-flight';
+    } else {
+      return 'setup-fatal';
+    }
   }
 
   protected function getResponseBody() {
-    return $this->view->render();
+    $view = $this->view;
+
+    if (PhabricatorSetupCheck::isInFlight()) {
+      return $view->renderInFlight();
+    } else {
+      return $view->render();
+    }
   }
 
   protected function buildPlainTextResponseString() {
diff --git a/src/applications/config/view/PhabricatorInFlightErrorView.php b/src/applications/config/view/PhabricatorInFlightErrorView.php
new file mode 100644
index 0000000000..2f1ad7bc33
--- /dev/null
+++ b/src/applications/config/view/PhabricatorInFlightErrorView.php
@@ -0,0 +1,41 @@
+<?php
+
+final class PhabricatorInFlightErrorView extends AphrontView {
+
+  private $message;
+
+  public function setMessage($message) {
+    $this->message = $message;
+    return $this;
+  }
+
+  public function getMessage() {
+    return $this->message;
+  }
+
+  public function render() {
+    return phutil_tag(
+      'div',
+      array(
+        'class' => 'in-flight-error-detail',
+      ),
+      array(
+        phutil_tag(
+          'h1',
+          array(
+            'class' => 'in-flight-error-title',
+          ),
+          pht('A Troublesome Encounter!')),
+        phutil_tag(
+          'div',
+          array(
+            'class' => 'in-flight-error-body',
+          ),
+          pht(
+            'Woe! This request had its journey cut short by unexpected '.
+            'circumstances (%s).',
+            $this->getMessage())),
+      ));
+  }
+
+}
diff --git a/src/applications/config/view/PhabricatorSetupIssueView.php b/src/applications/config/view/PhabricatorSetupIssueView.php
index a2a703c436..ca6397133d 100644
--- a/src/applications/config/view/PhabricatorSetupIssueView.php
+++ b/src/applications/config/view/PhabricatorSetupIssueView.php
@@ -13,6 +13,14 @@ final class PhabricatorSetupIssueView extends AphrontView {
     return $this->issue;
   }
 
+  public function renderInFlight() {
+    $issue = $this->getIssue();
+
+    return id(new PhabricatorInFlightErrorView())
+      ->setMessage($issue->getName())
+      ->render();
+  }
+
   public function render() {
     $issue = $this->getIssue();
 
diff --git a/webroot/rsrc/css/application/config/config-template.css b/webroot/rsrc/css/application/config/config-template.css
index bb8db22c93..13ce56488a 100644
--- a/webroot/rsrc/css/application/config/config-template.css
+++ b/webroot/rsrc/css/application/config/config-template.css
@@ -11,3 +11,27 @@ body {
   text-align: left;
   -webkit-text-size-adjust: none;
 }
+
+body.in-flight {
+  background: #41506e;
+  color: #e0e0e0;
+}
+
+.in-flight-error-detail {
+  max-width: 760px;
+  margin: 72px auto;
+  background: rgba(255, 255, 255, 0.25);
+  border-radius: 3px;
+  padding: 8px 16px;
+}
+
+.in-flight-error-title {
+   padding: 12px 8px;
+   font-size: 24px;
+   font-weight: 500;
+   margin: 0;
+}
+
+.in-flight-error-body {
+   padding: 4px 12px 12px;
+}