diff --git a/src/settings-ui/Settings.UI/SettingsXAML/Flyout/LaunchPage.xaml b/src/settings-ui/Settings.UI/SettingsXAML/Flyout/LaunchPage.xaml
index 0f1a241b25..8bb57e9e9f 100644
--- a/src/settings-ui/Settings.UI/SettingsXAML/Flyout/LaunchPage.xaml
+++ b/src/settings-ui/Settings.UI/SettingsXAML/Flyout/LaunchPage.xaml
@@ -7,6 +7,7 @@
     xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
     xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
     xmlns:tkcontrols="using:CommunityToolkit.WinUI.Controls"
+    xmlns:tkconverters="using:CommunityToolkit.WinUI.Converters"
     xmlns:ui="using:CommunityToolkit.WinUI"
     xmlns:viewModels="using:Microsoft.PowerToys.Settings.UI.ViewModels"
     mc:Ignorable="d">
@@ -20,6 +21,8 @@
             <Setter Property="Height" Value="32" />
             <Setter Property="FontFamily" Value="{ThemeResource SymbolThemeFontFamily}" />
         </Style>
+
+        <tkconverters:StringVisibilityConverter x:Key="StringVisibilityConverter" />
     </Page.Resources>
     <Grid>
         <Grid.RowDefinitions>
@@ -79,7 +82,6 @@
                                 AutomationProperties.Name="{x:Bind Label}"
                                 Click="ModuleButton_Click"
                                 Tag="{x:Bind Tag}"
-                                ToolTipService.ToolTip="{x:Bind ToolTip}"
                                 Visibility="{x:Bind Visible, Mode=TwoWay, UpdateSourceTrigger=PropertyChanged, Converter={StaticResource BoolToVisibilityConverter}}">
                                 <controls:FlyoutMenuButton.Content>
                                     <TextBlock
@@ -95,6 +97,9 @@
                                         </Image.Source>
                                     </Image>
                                 </controls:FlyoutMenuButton.Icon>
+                                <ToolTipService.ToolTip>
+                                    <ToolTip Content="{x:Bind ToolTip}" Visibility="{x:Bind ToolTip, Converter={StaticResource StringVisibilityConverter}}" />
+                                </ToolTipService.ToolTip>
                             </controls:FlyoutMenuButton>
                         </DataTemplate>
                     </ItemsControl.ItemTemplate>
diff --git a/src/settings-ui/Settings.UI/SettingsXAML/FlyoutWindow.xaml.cs b/src/settings-ui/Settings.UI/SettingsXAML/FlyoutWindow.xaml.cs
index c816561034..1835f474a1 100644
--- a/src/settings-ui/Settings.UI/SettingsXAML/FlyoutWindow.xaml.cs
+++ b/src/settings-ui/Settings.UI/SettingsXAML/FlyoutWindow.xaml.cs
@@ -80,13 +80,14 @@ namespace Microsoft.PowerToys.Settings.UI
 
                     this.MoveAndResize(newPosition.X, newPosition.Y, WindowWidth, WindowHeight);
                 }
+
+                FlyoutShellPage.SwitchToLaunchPage();
             }
 
             if (args.WindowActivationState == Microsoft.UI.Xaml.WindowActivationState.Deactivated)
             {
                 if (ViewModel.CanHide)
                 {
-                    FlyoutShellPage.SwitchToLaunchPage();
                     this.Hide();
                 }
             }
diff --git a/src/settings-ui/Settings.UI/ViewModels/DashboardViewModel.cs b/src/settings-ui/Settings.UI/ViewModels/DashboardViewModel.cs
index 24e30b1cac..cd489b4230 100644
--- a/src/settings-ui/Settings.UI/ViewModels/DashboardViewModel.cs
+++ b/src/settings-ui/Settings.UI/ViewModels/DashboardViewModel.cs
@@ -18,7 +18,6 @@ using Microsoft.PowerToys.Settings.UI.Services;
 using Microsoft.PowerToys.Settings.UI.Views;
 using Microsoft.UI.Xaml;
 using Microsoft.UI.Xaml.Controls;
-using Windows.UI;
 
 namespace Microsoft.PowerToys.Settings.UI.ViewModels
 {
@@ -443,9 +442,14 @@ namespace Microsoft.PowerToys.Settings.UI.ViewModels
         private ObservableCollection<DashboardModuleItem> GetModuleItemsShortcutGuide()
         {
             ISettingsRepository<ShortcutGuideSettings> moduleSettingsRepository = SettingsRepository<ShortcutGuideSettings>.GetInstance(new SettingsUtils());
+
+            var shortcut = moduleSettingsRepository.SettingsConfig.Properties.UseLegacyPressWinKeyBehavior.Value
+                ? new List<object> { 92 } // Right Windows key code
+                : moduleSettingsRepository.SettingsConfig.Properties.OpenShortcutGuide.GetKeysList();
+
             var list = new List<DashboardModuleItem>
             {
-                new DashboardModuleShortcutItem() { Label = resourceLoader.GetString("ShortcutGuide_ShortDescription"), Shortcut = moduleSettingsRepository.SettingsConfig.Properties.OpenShortcutGuide.GetKeysList() },
+                new DashboardModuleShortcutItem() { Label = resourceLoader.GetString("ShortcutGuide_ShortDescription"), Shortcut = shortcut },
             };
             return new ObservableCollection<DashboardModuleItem>(list);
         }
diff --git a/src/settings-ui/Settings.UI/ViewModels/Flyout/LauncherViewModel.cs b/src/settings-ui/Settings.UI/ViewModels/Flyout/LauncherViewModel.cs
index bec41d89b0..5e6ce8e0c3 100644
--- a/src/settings-ui/Settings.UI/ViewModels/Flyout/LauncherViewModel.cs
+++ b/src/settings-ui/Settings.UI/ViewModels/Flyout/LauncherViewModel.cs
@@ -76,12 +76,12 @@ namespace Microsoft.PowerToys.Settings.UI.ViewModels
                 Label = resourceLoader.GetString(ModuleHelper.GetModuleLabelResourceName(moduleType)),
                 Tag = moduleType,
                 Visible = ModuleHelper.GetIsModuleEnabled(generalSettingsConfig, moduleType),
-                ToolTip = GetModuleTooltip(moduleType),
+                ToolTip = GetModuleToolTip(moduleType),
                 Icon = ModuleHelper.GetModuleTypeFluentIconName(moduleType),
             });
         }
 
-        private string GetModuleTooltip(ModuleType moduleType)
+        private string GetModuleToolTip(ModuleType moduleType)
         {
             return moduleType switch
             {
@@ -90,7 +90,7 @@ namespace Microsoft.PowerToys.Settings.UI.ViewModels
                 ModuleType.PowerLauncher => SettingsRepository<PowerLauncherSettings>.GetInstance(new SettingsUtils()).SettingsConfig.Properties.OpenPowerLauncher.ToString(),
                 ModuleType.PowerOCR => SettingsRepository<PowerOcrSettings>.GetInstance(new SettingsUtils()).SettingsConfig.Properties.ActivationShortcut.ToString(),
                 ModuleType.MeasureTool => SettingsRepository<MeasureToolSettings>.GetInstance(new SettingsUtils()).SettingsConfig.Properties.ActivationShortcut.ToString(),
-                ModuleType.ShortcutGuide => SettingsRepository<ShortcutGuideSettings>.GetInstance(new SettingsUtils()).SettingsConfig.Properties.OpenShortcutGuide.ToString(),
+                ModuleType.ShortcutGuide => GetShortcutGuideToolTip(),
                 _ => string.Empty,
             };
         }
@@ -105,6 +105,14 @@ namespace Microsoft.PowerToys.Settings.UI.ViewModels
             }
         }
 
+        private string GetShortcutGuideToolTip()
+        {
+            var shortcutGuideSettings = SettingsRepository<ShortcutGuideSettings>.GetInstance(new SettingsUtils()).SettingsConfig;
+            return shortcutGuideSettings.Properties.UseLegacyPressWinKeyBehavior.Value
+                ? "Win"
+                : shortcutGuideSettings.Properties.OpenShortcutGuide.ToString();
+        }
+
         internal void StartBugReport()
         {
             SendIPCMessage("{\"bugreport\": 0 }");