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
@@ -1894,6 +1894,7 @@
     'PhabricatorHashTestCase' => 'infrastructure/util/__tests__/PhabricatorHashTestCase.php',
     'PhabricatorHelpApplication' => 'applications/help/application/PhabricatorHelpApplication.php',
     'PhabricatorHelpController' => 'applications/help/controller/PhabricatorHelpController.php',
+    'PhabricatorHelpDocumentationController' => 'applications/help/controller/PhabricatorHelpDocumentationController.php',
     'PhabricatorHelpEditorProtocolController' => 'applications/help/controller/PhabricatorHelpEditorProtocolController.php',
     'PhabricatorHelpKeyboardShortcutController' => 'applications/help/controller/PhabricatorHelpKeyboardShortcutController.php',
     'PhabricatorHeraldApplication' => 'applications/herald/application/PhabricatorHeraldApplication.php',
@@ -5232,6 +5233,7 @@
     'PhabricatorHashTestCase' => 'PhabricatorTestCase',
     'PhabricatorHelpApplication' => 'PhabricatorApplication',
     'PhabricatorHelpController' => 'PhabricatorController',
+    'PhabricatorHelpDocumentationController' => 'PhabricatorHelpController',
     'PhabricatorHelpEditorProtocolController' => 'PhabricatorHelpController',
     'PhabricatorHelpKeyboardShortcutController' => 'PhabricatorHelpController',
     'PhabricatorHeraldApplication' => 'PhabricatorApplication',
diff --git a/src/applications/almanac/application/PhabricatorAlmanacApplication.php b/src/applications/almanac/application/PhabricatorAlmanacApplication.php
--- a/src/applications/almanac/application/PhabricatorAlmanacApplication.php
+++ b/src/applications/almanac/application/PhabricatorAlmanacApplication.php
@@ -26,8 +26,13 @@
     return self::GROUP_UTILITIES;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Almanac User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Alamanac User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Almanac User Guide'),
+      ),
+    );
   }
 
   public function isPrototype() {
diff --git a/src/applications/audit/application/PhabricatorAuditApplication.php b/src/applications/audit/application/PhabricatorAuditApplication.php
--- a/src/applications/audit/application/PhabricatorAuditApplication.php
+++ b/src/applications/audit/application/PhabricatorAuditApplication.php
@@ -22,8 +22,13 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Audit User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Audit User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Audit User Guide'),
+      ),
+    );
   }
 
   public function getRoutes() {
diff --git a/src/applications/auth/application/PhabricatorAuthApplication.php b/src/applications/auth/application/PhabricatorAuthApplication.php
--- a/src/applications/auth/application/PhabricatorAuthApplication.php
+++ b/src/applications/auth/application/PhabricatorAuthApplication.php
@@ -26,16 +26,16 @@
     return pht('Login/Registration');
   }
 
-  public function getHelpURI() {
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
     // NOTE: Although reasonable help exists for this in "Configuring Accounts
-    // and Registration", specifying a help URI here means we get the menu
+    // and Registration", specifying help items here means we get the menu
     // item in all the login/link interfaces, which is confusing and not
     // helpful.
 
     // TODO: Special case this, or split the auth and auth administration
     // applications?
 
-    return null;
+    return array();
   }
 
   public function buildMainMenuItems(
diff --git a/src/applications/base/PhabricatorApplication.php b/src/applications/base/PhabricatorApplication.php
--- a/src/applications/base/PhabricatorApplication.php
+++ b/src/applications/base/PhabricatorApplication.php
@@ -169,8 +169,48 @@
     return null;
   }
 
-  public function getHelpURI() {
-    return null;
+  public function getHelpMenuItems(PhabricatorUser $viewer) {
+    $items = array();
+
+    $articles = $this->getHelpDocumentationArticles($viewer);
+    if ($articles) {
+      $items[] = id(new PHUIListItemView())
+        ->setType(PHUIListItemView::TYPE_LABEL)
+        ->setName(pht('%s Documentation', $this->getName()));
+      foreach ($articles as $article) {
+        $item = id(new PHUIListItemView())
+          ->setName($article['name'])
+          ->setIcon('fa-book')
+          ->setHref($article['href']);
+
+        $items[] = $item;
+      }
+    }
+
+    $command_specs = $this->getMailCommandObjects();
+    if ($command_specs) {
+      $items[] = id(new PHUIListItemView())
+        ->setType(PHUIListItemView::TYPE_LABEL)
+        ->setName(pht('Email Help'));
+      foreach ($command_specs as $key => $spec) {
+        $object = $spec['object'];
+
+        $class = get_class($this);
+        $href = '/applications/mailcommands/'.$class.'/'.$key.'/';
+
+        $item = id(new PHUIListItemView())
+          ->setName($spec['name'])
+          ->setIcon('fa-envelope-o')
+          ->setHref($href);
+        $items[] = $item;
+      }
+    }
+
+    return $items;
+  }
+
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array();
   }
 
   public function getOverview() {
diff --git a/src/applications/conduit/application/PhabricatorConduitApplication.php b/src/applications/conduit/application/PhabricatorConduitApplication.php
--- a/src/applications/conduit/application/PhabricatorConduitApplication.php
+++ b/src/applications/conduit/application/PhabricatorConduitApplication.php
@@ -14,8 +14,13 @@
     return false;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Conduit Technical Documentation');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Conduit Technical Documentation'),
+        'href' => PhabricatorEnv::getDoclink('Conduit Technical Documentation'),
+      ),
+    );
   }
 
   public function getName() {
diff --git a/src/applications/differential/application/PhabricatorDifferentialApplication.php b/src/applications/differential/application/PhabricatorDifferentialApplication.php
--- a/src/applications/differential/application/PhabricatorDifferentialApplication.php
+++ b/src/applications/differential/application/PhabricatorDifferentialApplication.php
@@ -22,8 +22,13 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Differential User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Differential User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Differential User Guide'),
+      ),
+    );
   }
 
   public function getFactObjectsForAnalysis() {
@@ -189,6 +194,7 @@
   public function getMailCommandObjects() {
     return array(
       'revision' => array(
+        'name' => pht('Email Commands: Revisions'),
         'object' => new DifferentialRevision(),
       ),
     );
diff --git a/src/applications/diffusion/application/PhabricatorDiffusionApplication.php b/src/applications/diffusion/application/PhabricatorDiffusionApplication.php
--- a/src/applications/diffusion/application/PhabricatorDiffusionApplication.php
+++ b/src/applications/diffusion/application/PhabricatorDiffusionApplication.php
@@ -22,8 +22,13 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Diffusion User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Diffusion User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Diffusion User Guide'),
+      ),
+    );
   }
 
   public function getFactObjectsForAnalysis() {
diff --git a/src/applications/drydock/application/PhabricatorDrydockApplication.php b/src/applications/drydock/application/PhabricatorDrydockApplication.php
--- a/src/applications/drydock/application/PhabricatorDrydockApplication.php
+++ b/src/applications/drydock/application/PhabricatorDrydockApplication.php
@@ -34,8 +34,13 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Drydock User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Drydock User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Drydock User Guide'),
+      ),
+    );
   }
 
   public function getRoutes() {
diff --git a/src/applications/help/application/PhabricatorHelpApplication.php b/src/applications/help/application/PhabricatorHelpApplication.php
--- a/src/applications/help/application/PhabricatorHelpApplication.php
+++ b/src/applications/help/application/PhabricatorHelpApplication.php
@@ -19,6 +19,8 @@
       '/help/' => array(
         'keyboardshortcut/' => 'PhabricatorHelpKeyboardShortcutController',
         'editorprotocol/' => 'PhabricatorHelpEditorProtocolController',
+        'documentation/(?P<application>\w+)/'
+          => 'PhabricatorHelpDocumentationController',
       ),
     );
   }
@@ -27,27 +29,75 @@
     PhabricatorUser $user,
     PhabricatorController $controller = null) {
 
-    $items = array();
-
     $application = null;
     if ($controller) {
       $application = $controller->getCurrentApplication();
     }
 
-    if ($application && $application->getHelpURI()) {
-      $help_name = pht('%s Help', $application->getName());
-
-      $item = id(new PHUIListItemView())
-        ->setName($help_name)
-        ->addClass('core-menu-item')
-        ->setIcon('fa-info-circle')
-        ->setAural($help_name)
-        ->setOrder(200)
-        ->setHref($application->getHelpURI());
-      $items[] = $item;
+    $items = array();
+    if ($application) {
+      $help_items = $application->getHelpMenuItems($user);
+      if ($help_items) {
+        $help_id = celerity_generate_unique_node_id();
+
+        Javelin::initBehavior(
+          'aphlict-dropdown',
+          array(
+            'bubbleID' => $help_id,
+            'dropdownID' => 'phabricator-help-menu',
+            'local' => true,
+            'desktop' => true,
+            'right' => true,
+          ));
+
+        $help_name = pht('%s Help', $application->getName());
+
+        $item = id(new PHUIListItemView())
+          ->setName($help_name)
+          ->setIcon('fa-life-ring')
+          ->setHref('/help/documentation/'.get_class($application).'/')
+          ->addClass('core-menu-item')
+          ->setID($help_id)
+          ->setAural($help_name)
+          ->setOrder(200);
+        $items[] = $item;
+      }
     }
 
     return $items;
   }
 
+  public function buildMainMenuExtraNodes(
+    PhabricatorUser $viewer,
+    PhabricatorController $controller = null) {
+
+    if (!$controller) {
+      return null;
+    }
+
+    $application = $controller->getCurrentApplication();
+    if (!$application) {
+      return null;
+    }
+
+    $help_items = $application->getHelpMenuItems($viewer);
+    if (!$help_items) {
+      return null;
+    }
+
+    $view = new PHUIListView();
+    foreach ($help_items as $item) {
+      $view->addMenuItem($item);
+    }
+
+    return phutil_tag(
+      'div',
+      array(
+        'id' => 'phabricator-help-menu',
+        'class' => 'phabricator-main-menu-dropdown phui-list-sidenav',
+        'style' => 'display: none',
+      ),
+      $view);
+  }
+
 }
diff --git a/src/applications/help/controller/PhabricatorHelpDocumentationController.php b/src/applications/help/controller/PhabricatorHelpDocumentationController.php
new file mode 100644
--- /dev/null
+++ b/src/applications/help/controller/PhabricatorHelpDocumentationController.php
@@ -0,0 +1,52 @@
+<?php
+
+final class PhabricatorHelpDocumentationController
+  extends PhabricatorHelpController {
+
+  public function shouldAllowPublic() {
+    return true;
+  }
+
+  public function handleRequest(AphrontRequest $request) {
+    $viewer = $this->getViewer();
+
+    $application_class = $request->getURIData('application');
+    $application = id(new PhabricatorApplicationQuery())
+      ->setViewer($viewer)
+      ->withClasses(array($application_class))
+      ->executeOne();
+    if (!$application) {
+      return new Aphront404Response();
+    }
+
+    $items = $application->getHelpMenuItems($viewer);
+    $title = pht('%s Help', $application->getName());
+
+    $list = id(new PHUIObjectItemListView())
+      ->setUser($viewer);
+    foreach ($items as $item) {
+      if ($item->getType() == PHUIListItemView::TYPE_LABEL) {
+        continue;
+      }
+      $list->addItem(
+        id(new PHUIObjectItemView())
+          ->setHeader($item->getName())
+          ->setWorkflow($item->getWorkflow())
+          ->setHref($item->getHref()));
+    }
+
+    $crumbs = $this->buildApplicationCrumbs();
+    $crumbs->addTextCrumb($title);
+
+    return $this->buildApplicationPage(
+      array(
+        $crumbs,
+        $list,
+      ),
+      array(
+        'title' => $title,
+      ));
+  }
+
+
+}
diff --git a/src/applications/herald/application/PhabricatorHeraldApplication.php b/src/applications/herald/application/PhabricatorHeraldApplication.php
--- a/src/applications/herald/application/PhabricatorHeraldApplication.php
+++ b/src/applications/herald/application/PhabricatorHeraldApplication.php
@@ -22,8 +22,13 @@
     return "\xE2\x98\xBF";
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Herald User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Herald User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Herald User Guide'),
+      ),
+    );
   }
 
   public function getFlavorText() {
diff --git a/src/applications/home/controller/PhabricatorHomeQuickCreateController.php b/src/applications/home/controller/PhabricatorHomeQuickCreateController.php
--- a/src/applications/home/controller/PhabricatorHomeQuickCreateController.php
+++ b/src/applications/home/controller/PhabricatorHomeQuickCreateController.php
@@ -32,5 +32,4 @@
       ));
   }
 
-
 }
diff --git a/src/applications/legalpad/application/PhabricatorLegalpadApplication.php b/src/applications/legalpad/application/PhabricatorLegalpadApplication.php
--- a/src/applications/legalpad/application/PhabricatorLegalpadApplication.php
+++ b/src/applications/legalpad/application/PhabricatorLegalpadApplication.php
@@ -32,8 +32,13 @@
     );
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Legalpad User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Legalpad User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Legalpad User Guide'),
+      ),
+    );
   }
 
   public function getOverview() {
diff --git a/src/applications/maniphest/application/PhabricatorManiphestApplication.php b/src/applications/maniphest/application/PhabricatorManiphestApplication.php
--- a/src/applications/maniphest/application/PhabricatorManiphestApplication.php
+++ b/src/applications/maniphest/application/PhabricatorManiphestApplication.php
@@ -146,6 +146,7 @@
   public function getMailCommandObjects() {
     return array(
       'task' => array(
+        'name' => pht('Email Commands: Tasks'),
         'object' => new ManiphestTask(),
       ),
     );
diff --git a/src/applications/meta/controller/PhabricatorApplicationDetailViewController.php b/src/applications/meta/controller/PhabricatorApplicationDetailViewController.php
--- a/src/applications/meta/controller/PhabricatorApplicationDetailViewController.php
+++ b/src/applications/meta/controller/PhabricatorApplicationDetailViewController.php
@@ -138,14 +138,6 @@
       ->setUser($user)
       ->setObjectURI($this->getRequest()->getRequestURI());
 
-    if ($selected->getHelpURI()) {
-      $view->addAction(
-        id(new PhabricatorActionView())
-          ->setName(pht('Help / Documentation'))
-          ->setIcon('fa-life-ring')
-          ->setHref($selected->getHelpURI()));
-    }
-
     $can_edit = PhabricatorPolicyFilter::hasCapability(
       $user,
       $selected,
diff --git a/src/applications/meta/controller/PhabricatorApplicationEmailCommandsController.php b/src/applications/meta/controller/PhabricatorApplicationEmailCommandsController.php
--- a/src/applications/meta/controller/PhabricatorApplicationEmailCommandsController.php
+++ b/src/applications/meta/controller/PhabricatorApplicationEmailCommandsController.php
@@ -78,9 +78,11 @@
 
     $content = implode("\n\n", $content);
 
+    $title = $spec['name'];
+
     $crumbs = $this->buildApplicationCrumbs();
     $this->addApplicationCrumb($crumbs, $selected);
-    $crumbs->addTextCrumb(pht('Mail Commands'));
+    $crumbs->addTextCrumb($title);
 
     $content_box = id(new PHUIBoxView())
       ->addMargin(PHUI::MARGIN_LARGE)
@@ -91,7 +93,7 @@
           $viewer));
 
     $box = id(new PHUIObjectBoxView())
-      ->setHeaderText(pht('Mail Commands'))
+      ->setHeaderText($title)
       ->appendChild($content_box);
 
     return $this->buildApplicationPage(
@@ -100,7 +102,7 @@
         $box,
       ),
       array(
-        'title' => 'asdf',
+        'title' => $title,
       ));
 
   }
diff --git a/src/applications/oauthserver/application/PhabricatorOAuthServerApplication.php b/src/applications/oauthserver/application/PhabricatorOAuthServerApplication.php
--- a/src/applications/oauthserver/application/PhabricatorOAuthServerApplication.php
+++ b/src/applications/oauthserver/application/PhabricatorOAuthServerApplication.php
@@ -34,8 +34,14 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Using the Phabricator OAuth Server');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Using the Phabricator OAuth Server'),
+        'href' => PhabricatorEnv::getDoclink(
+          'Using the Phabricator OAuth Server'),
+      ),
+    );
   }
 
   public function getRoutes() {
diff --git a/src/applications/owners/application/PhabricatorOwnersApplication.php b/src/applications/owners/application/PhabricatorOwnersApplication.php
--- a/src/applications/owners/application/PhabricatorOwnersApplication.php
+++ b/src/applications/owners/application/PhabricatorOwnersApplication.php
@@ -22,8 +22,13 @@
     return "\xE2\x98\x81";
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Owners Tool User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Owners User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Owners Tool User Guide'),
+      ),
+    );
   }
 
   public function getFlavorText() {
diff --git a/src/applications/phame/application/PhabricatorPhameApplication.php b/src/applications/phame/application/PhabricatorPhameApplication.php
--- a/src/applications/phame/application/PhabricatorPhameApplication.php
+++ b/src/applications/phame/application/PhabricatorPhameApplication.php
@@ -22,8 +22,13 @@
     return "\xe2\x9c\xa9";
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Phame User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Phame User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Phame User Guide'),
+      ),
+    );
   }
 
   public function isPrototype() {
diff --git a/src/applications/phriction/application/PhabricatorPhrictionApplication.php b/src/applications/phriction/application/PhabricatorPhrictionApplication.php
--- a/src/applications/phriction/application/PhabricatorPhrictionApplication.php
+++ b/src/applications/phriction/application/PhabricatorPhrictionApplication.php
@@ -22,8 +22,13 @@
     return true;
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Phriction User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Phriction User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Phriction User Guide'),
+      ),
+    );
   }
 
   public function getTitleGlyph() {
diff --git a/src/applications/slowvote/application/PhabricatorSlowvoteApplication.php b/src/applications/slowvote/application/PhabricatorSlowvoteApplication.php
--- a/src/applications/slowvote/application/PhabricatorSlowvoteApplication.php
+++ b/src/applications/slowvote/application/PhabricatorSlowvoteApplication.php
@@ -22,8 +22,13 @@
     return "\xE2\x9C\x94";
   }
 
-  public function getHelpURI() {
-    return PhabricatorEnv::getDoclink('Slowvote User Guide');
+  public function getHelpDocumentationArticles(PhabricatorUser $viewer) {
+    return array(
+      array(
+        'name' => pht('Slowvote User Guide'),
+        'href' => PhabricatorEnv::getDoclink('Slowvote User Guide'),
+      ),
+    );
   }
 
   public function getFlavorText() {