diff --git a/dev/MenuBar/MenuBar.cpp b/dev/MenuBar/MenuBar.cpp
index 65b889095a..40d90b2dab 100644
--- a/dev/MenuBar/MenuBar.cpp
+++ b/dev/MenuBar/MenuBar.cpp
@@ -26,11 +26,6 @@ winrt::AutomationPeer MenuBar::OnCreateAutomationPeer()
 void MenuBar::OnApplyTemplate()
 {
     SetUpTemplateParts();
-    
-    for (auto const& menuBarItem : Items())
-    {
-        winrt::get_self<MenuBarItem>(menuBarItem)->AddPassThroughElement(m_layoutRoot.get());
-    }
 }
 
 void MenuBar::SetUpTemplateParts()
@@ -54,6 +49,12 @@ void MenuBar::SetUpTemplateParts()
     }
 }
 
+void MenuBar::RequestPassThroughElement(const winrt::Microsoft::UI::Xaml::Controls::MenuBarItem& menuBarItem)
+{
+    // To enable switching flyout on hover, every menubar item needs the MenuBar root to include it for hit detection with flyouts open
+    winrt::get_self<MenuBarItem>(menuBarItem)->AddPassThroughElement(m_layoutRoot.get());
+}
+
 void MenuBar::IsFlyoutOpen(bool state)
 {
     m_isFlyoutOpen = state;
diff --git a/dev/MenuBar/MenuBar.h b/dev/MenuBar/MenuBar.h
index 0443105ea5..6937bebfe9 100644
--- a/dev/MenuBar/MenuBar.h
+++ b/dev/MenuBar/MenuBar.h
@@ -18,6 +18,8 @@ class MenuBar :
     bool IsFlyoutOpen() { return m_isFlyoutOpen; };
     void IsFlyoutOpen(bool state);
 
+    void RequestPassThroughElement(const winrt::Microsoft::UI::Xaml::Controls::MenuBarItem& menuBarItem);
+
 public:
     // IUIElement / IUIElementOverridesHelper
     winrt::AutomationPeer OnCreateAutomationPeer();
diff --git a/dev/MenuBar/MenuBarItem.cpp b/dev/MenuBar/MenuBarItem.cpp
index 2b5de81e03..6479bd183f 100644
--- a/dev/MenuBar/MenuBarItem.cpp
+++ b/dev/MenuBar/MenuBarItem.cpp
@@ -36,15 +36,17 @@ void MenuBarItem::OnApplyTemplate()
 {
     m_button.set(GetTemplateChildT<winrt::Button>(L"ContentButton", *this));
 
-    PopulateContent();
-    DetachEventHandlers();
-    AttachEventHandlers();
-
     auto menuBar = SharedHelpers::GetAncestorOfType<winrt::MenuBar>(winrt::VisualTreeHelper::GetParent(*this));
     if (menuBar)
     {
         m_menuBar = winrt::make_weak(menuBar);
+        // Ask parent MenuBar for its root to enable pass through
+        winrt::get_self<MenuBar>(menuBar)->RequestPassThroughElement(*this);
     }
+
+    PopulateContent();
+    DetachEventHandlers();
+    AttachEventHandlers();
 }
 
 void MenuBarItem::PopulateContent()
diff --git a/dev/MenuBar/MenuBar_InteractionTests/MenuBarTests.cs b/dev/MenuBar/MenuBar_InteractionTests/MenuBarTests.cs
index 3eac105f27..3c20da119f 100644
--- a/dev/MenuBar/MenuBar_InteractionTests/MenuBarTests.cs
+++ b/dev/MenuBar/MenuBar_InteractionTests/MenuBarTests.cs
@@ -307,6 +307,49 @@ public void MenuBarHeightTest()
             }
         }
 
+        [TestMethod]
+        public void HoveringBehaviorTest()
+        {
+            // Overlay pass through element is only available from IFlyoutBase3 forward
+            // On OS versions below RS5 test is unreliable/not working.
+            // Tracked by https://github.com/Microsoft/microsoft-ui-xaml/issues/115
+            if (PlatformConfiguration.IsDevice(DeviceType.Phone) 
+                || !ApiInformation.IsTypePresent("Windows.UI.Xaml.Controls.Primitives.IFlyoutBase3")
+                || PlatformConfiguration.IsOSVersionLessThan(OSVersion.Redstone4))
+            {
+                Log.Comment("Skipping tests on phone, because menubar is not supported.");
+                return;
+            }
+            using (var setup = new TestSetupHelper("MenuBar Tests"))
+            {
+                var menuBar = FindElement.ById("SizedMenuBar");
+                var addButton = FindElement.ByName("AddItemsToEmptyMenuBar");
+
+                addButton.Click();
+                addButton.Click();
+                addButton.Click();
+
+                var help0 = FindElement.ByName<Button>("Help0");
+                var help1 = FindElement.ByName<Button>("Help1");
+
+                // This behavior seems to a bit unreliable, so repeat
+                InputHelper.LeftClick(help0);
+                TestEnvironment.VerifyAreEqualWithRetry(20,
+                    () => FindCore.ByName("Add0", shouldWait: false) != null, // The item should be in the tree
+                    () => true);
+
+                // Check if hovering over the next button actually will show the correct item
+                VerifyElement.NotFound("Add1", FindBy.Name);
+                InputHelper.MoveMouse(help1, 0, 0);
+                InputHelper.MoveMouse(help1, 1, 1);
+                InputHelper.MoveMouse(help1, 5, 5);
+
+                UIObject add1Element = null;
+                ElementCache.Clear();
+                var element = GetElement(ref add1Element, "Add1");
+                Verify.IsNotNull(add1Element);
+            }
+        }
 
         [TestMethod]
         public void TabTest()
@@ -331,5 +374,17 @@ public void TabTest()
                 Verify.AreEqual(true, fileButton.HasKeyboardFocus);
             }
         }
+
+
+        private T GetElement<T>(ref T element, string elementName) where T : UIObject
+        {
+            if (element == null)
+            {
+                Log.Comment("Find the " + elementName);
+                element = FindElement.ByNameOrId<T>(elementName);
+                Verify.IsNotNull(element);
+            }
+            return element;
+        }
     }
 }
diff --git a/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml b/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml
index 4141e90411..2c80bb746e 100644
--- a/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml
+++ b/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml
@@ -22,6 +22,7 @@
             <Button AutomationProperties.Name="FirstButton" Content="Element to test that focus moves correctly"/>
 
             <TextBlock Text="Sample controls" Style="{ThemeResource StandardGroupHeader}"/>
+            <TextBlock Text="Sample menu bar"/>
             <muxc:MenuBar x:Name="menuBar">
                 <muxc:MenuBarItem x:Name="FileItem" AutomationProperties.Name="FileItem" Title="File">
                     <MenuFlyoutItem x:Name="NewItem" AutomationProperties.Name="NewItem" Text="New" Click="NewItem_Click"/>
@@ -55,10 +56,14 @@
                     <MenuFlyoutItem Text="Font..."/>
                 </muxc:MenuBarItem>
             </muxc:MenuBar>
-            
+
+            <TextBlock Text="Custom sized menu bar" Margin="0,6,0,0"/>
             <muxc:MenuBar x:Name="SizedMenuBar" AutomationProperties.Name="SizedMenuBar" Height="24">
                 <muxc:MenuBarItem x:Name="SizedMenuBarItem" AutomationProperties.Name="SizedMenuBarItem" Title="Size"/>
             </muxc:MenuBar>
+
+            <TextBlock Text="Initially empty menubar" Margin="0,6,0,0"/>
+            <muxc:MenuBar x:Name="EmptyMenuBar"></muxc:MenuBar>
         </StackPanel>
         <TextBlock Grid.Row="1" Text="Options" Style="{ThemeResource StandardGroupHeader}"/>
         <StackPanel Margin="0,20,0,20" VerticalAlignment="Top"  Grid.Row="2" Orientation="Horizontal">
@@ -72,6 +77,7 @@
             <Button x:Name="RemoveMenuBarItemButton" AutomationProperties.Name="RemoveMenuBarItemButton" Click="RemoveMenuBarItem_Click" Content="Remove Menu Bar Item"/>
             <Button x:Name="AddFlyoutItemButton" AutomationProperties.Name="AddFlyoutItemButton" Click="AddFlyoutItem_Click" Content="Add Flyout Item"/>
             <Button x:Name="RemoveFlyoutItemButton" AutomationProperties.Name="RemoveFlyoutItemButton" Click="RemoveFlyoutItem_Click" Content="Remove Flyout Item"/>
+            <Button x:Name="AddItemsToEmptyMenuBar" AutomationProperties.Name="AddItemsToEmptyMenuBar" Click="AddMenuBarToEmptyMenuBarItem_Click" Content="Add a menu item to the empty menu bar"/>
         </StackPanel>
         <StackPanel Grid.Row="3">
             <TextBlock Text="Test output" Style="{ThemeResource StandardGroupHeader}"/>
diff --git a/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml.cs b/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml.cs
index 59ffb33f0a..9d1b867bcb 100644
--- a/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml.cs
+++ b/dev/MenuBar/MenuBar_TestUI/MenuBarPage.xaml.cs
@@ -3,6 +3,7 @@
 
 using Windows.Foundation.Metadata;
 using Windows.UI.Xaml;
+using Windows.UI.Xaml.Automation;
 using Windows.UI.Xaml.Controls;
 using Windows.UI.Xaml.Input;
 
@@ -91,5 +92,21 @@ private void TestFrameCheckbox_Unchecked(object sender, RoutedEventArgs e)
             var testFrame = Window.Current.Content as TestFrame;
             testFrame.ChangeBarVisibility(Visibility.Collapsed);
         }
+
+        private void AddMenuBarToEmptyMenuBarItem_Click(object sender, RoutedEventArgs e)
+        {
+            int eCount = EmptyMenuBar.Items.Count;
+            MenuBarItem mainMenuBarHelp = new MenuBarItem();
+            mainMenuBarHelp.Title = "Help" + eCount;
+            mainMenuBarHelp.SetValue(AutomationProperties.NameProperty, "Help" + eCount);
+            MenuFlyoutItem newFlyout = new MenuFlyoutItem() { Text = "Add" + eCount };
+            // UIA Name for interaction test
+            newFlyout.SetValue(AutomationProperties.NameProperty, "Add" + eCount);
+            mainMenuBarHelp.Items.Add(newFlyout);
+
+            mainMenuBarHelp.Items.Add(new MenuFlyoutItem() { Text = "Remove" + eCount });
+            EmptyMenuBar.Items.Add(mainMenuBarHelp);
+        }
+
     }
 }