diff --git a/src/Framework/Features/Navigation/NavigationMenu.php b/src/Framework/Features/Navigation/NavigationMenu.php
index bcc844dc..adf939a7 100644
--- a/src/Framework/Features/Navigation/NavigationMenu.php
+++ b/src/Framework/Features/Navigation/NavigationMenu.php
@@ -11,6 +11,8 @@
 
 class NavigationMenu extends BaseNavigationMenu
 {
+    private bool $hasDropdowns;
+
     protected function generate(): void
     {
         parent::generate();
@@ -69,6 +71,13 @@ protected function canAddItemToDropdown(NavItem $item): bool
 
     protected function dropdownsEnabled(): bool
     {
-        return Config::getString('hyde.navigation.subdirectories', 'hidden') === 'dropdown';
+        return (Config::getString('hyde.navigation.subdirectories', 'hidden') === 'dropdown') || $this->hasGroupExplicitlySetInFrontMatter();
+    }
+
+    private function hasGroupExplicitlySetInFrontMatter(): bool
+    {
+        return $this->hasDropdowns ??= $this->items->contains(function (NavItem $item): bool {
+            return ($item->getGroup() !== null) && ($item->destination !== (string) DocumentationPage::home());
+        });
     }
 }
diff --git a/tests/Feature/NavigationMenuTest.php b/tests/Feature/NavigationMenuTest.php
index a36346e4..64450a9b 100644
--- a/tests/Feature/NavigationMenuTest.php
+++ b/tests/Feature/NavigationMenuTest.php
@@ -383,4 +383,38 @@ public function testDropdownMenuItemsAreSortedByPriority()
 
         $this->assertSame(['Foo', 'Bar', 'Baz'], $dropdowns[0]->getItems()->pluck('label')->toArray());
     }
+
+    public function testHasDropdownsReturnsTrueWhenGroupIsExplicitlySetInFrontMatter()
+    {
+        config(['hyde.navigation.subdirectories' => 'hidden']);
+
+        Routes::addRoute((new MarkdownPage('foo', matter: ['navigation.group' => 'test-group']))->getRoute());
+
+        $this->assertTrue(NavigationMenu::create()->hasDropdowns());
+    }
+
+    public function testGetDropdownsReturnsCorrectArrayWhenGroupIsExplicitlySetInFrontMatter()
+    {
+        config(['hyde.navigation.subdirectories' => 'hidden']);
+
+        Routes::addRoute((new MarkdownPage('foo', matter: ['navigation.group' => 'test-group']))->getRoute());
+
+        $menu = NavigationMenu::create();
+        $this->assertCount(1, $menu->getDropdowns());
+
+        $this->assertEquals([
+            DropdownNavItem::fromArray('test-group', [
+                NavItem::fromRoute((new MarkdownPage('foo'))->getRoute()),
+            ]),
+        ], $menu->getDropdowns());
+    }
+
+    public function testHasDropdownsReturnsFalseWhenGroupIsNotExplicitlySetInFrontMatter()
+    {
+        config(['hyde.navigation.subdirectories' => 'hidden']);
+
+        Routes::addRoute((new MarkdownPage('foo'))->getRoute());
+        $menu = NavigationMenu::create();
+        $this->assertFalse($menu->hasDropdowns());
+    }
 }
diff --git a/tests/Unit/NavigationDataFactoryUnitTest.php b/tests/Unit/NavigationDataFactoryUnitTest.php
index a118c695..8074f2ef 100644
--- a/tests/Unit/NavigationDataFactoryUnitTest.php
+++ b/tests/Unit/NavigationDataFactoryUnitTest.php
@@ -146,6 +146,36 @@ public function testRouteKeysCanBeUsedForDocumentationSidebarPriorities()
         $this->assertSame(502, $factory->makePriority());
     }
 
+    public function testMakeGroupUsesFrontMatterGroupIfSet()
+    {
+        $frontMatter = new FrontMatter(['navigation.group' => 'Test Group']);
+        $coreDataObject = new CoreDataObject($frontMatter, new Markdown(), MarkdownPage::class, 'test.md', '', '', '');
+        $factory = new NavigationConfigTestClass($coreDataObject);
+
+        $this->assertSame('Test Group', $factory->makeGroup());
+    }
+
+    public function testMakeGroupUsesFrontMatterGroupIfSetRegardlessOfSubdirectoryConfiguration()
+    {
+        self::mockConfig(['hyde.navigation.subdirectories' => 'hidden']);
+
+        $frontMatter = new FrontMatter(['navigation.group' => 'Test Group']);
+        $coreDataObject = new CoreDataObject($frontMatter, new Markdown(), MarkdownPage::class, 'test.md', '', '', '');
+        $factory = new NavigationConfigTestClass($coreDataObject);
+
+        $this->assertSame('Test Group', $factory->makeGroup());
+    }
+
+    public function testMakeGroupDefaultsToNullIfFrontMatterGroupNotSetAndSubdirectoriesNotUsed()
+    {
+        self::mockConfig(['hyde.navigation.subdirectories' => 'hidden']);
+
+        $coreDataObject = new CoreDataObject(new FrontMatter(), new Markdown(), MarkdownPage::class, 'test.md', '', '', '');
+        $factory = new NavigationConfigTestClass($coreDataObject);
+
+        $this->assertNull($factory->makeGroup());
+    }
+
     protected function makeCoreDataObject(string $identifier = '', string $routeKey = '', string $pageClass = MarkdownPage::class): CoreDataObject
     {
         return new CoreDataObject(new FrontMatter(), new Markdown(), $pageClass, $identifier, '', '', $routeKey);
@@ -163,4 +193,9 @@ public function makePriority(): int
     {
         return parent::makePriority();
     }
+
+    public function makeGroup(): ?string
+    {
+        return parent::makeGroup();
+    }
 }