I guess you can't show a `ContentDialog` and a `TeachingTip` at the same time. Let me show you another way to do this by creating a custom dialog based on a `Window`:
                        
                        
                        
                        **CustomDialog.cs**
                        
                        ```cs
                        
                        using Microsoft.UI.Xaml;
                        
                        using System.Threading.Tasks;
                        
                        using WinUIEx;
                        
                        
                        
                        namespace App1;
                        
                        
                        
                        public enum CustomDialogResult
                        
                        {
                        
                            Cancel,
                        
                            OK,
                        
                        }
                        
                        
                        
                        public partial class CustomDialog : WindowEx
                        
                        {
                        
                            private TaskCompletionSource<CustomDialogResult>? _taskCompletionSource;
                        
                        
                        
                            public CustomDialog()
                        
                            {
                        
                                this.InitializeComponent();
                        
                                this.IsAlwaysOnTop = true;
                        
                                this.CenterOnScreen();
                        
                                this.SetWindowStyle(WindowStyle.Caption);
                        
                            }
                        
                            public new object? Content { get; set; }
                        
                        
                        
                            public Task<CustomDialogResult> ShowAsync()
                        
                            {
                        
                                this.ContentPresenter.Content = Content;
                        
                                _taskCompletionSource = new();
                        
                                this.Activate();
                        
                                return _taskCompletionSource.Task;
                        
                            }
                        
                        
                        
                            private void OKButton_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                                _taskCompletionSource?.SetResult(CustomDialogResult.OK);
                        
                                this.Close();
                        
                            }
                        
                        
                        
                            private void CancelButton_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                                _taskCompletionSource?.SetResult(CustomDialogResult.Cancel);
                        
                                this.Close();
                        
                            }
                        
                        }
                        
                        ```
                        
                        
                        
                        **CustomDialog.xaml.cs**
                        
                        ```xaml
                        
                        <ex:WindowEx
                        
                            x:Class="App1.CustomDialog"
                        
                            xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
                        
                            xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
                        
                            xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
                        
                            xmlns:ex="using:WinUIEx"
                        
                            xmlns:local="using:App1"
                        
                            xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
                        
                            Width="300"
                        
                            Height="200"
                        
                            mc:Ignorable="d">
                        
                        
                        
                            <Grid
                        
                                RowDefinitions="*,Auto">
                        
                                <ContentPresenter
                        
                                    x:Name="ContentPresenter"
                        
                                    Grid.Row="0" />
                        
                                <Grid
                        
                                    Grid.Row="1"
                        
                                    ColumnDefinitions="*,*">
                        
                                    <Button
                        
                                        Grid.Column="0"
                        
                                        Click="OKButton_Click"
                        
                                        Content="OK" />
                        
                                    <Button
                        
                                        Grid.Column="1"
                        
                                        Click="CancelButton_Click"
                        
                                        Content="Cancel" />
                        
                                </Grid>
                        
                            </Grid>
                        
                        </ex:WindowEx>
                        
                        ```
                        
                        
                        
                        then use it like this:
                        
                        
                        
                        ```cs
                        
                        public sealed partial class MainWindow : Window
                        
                        {
                        
                            public MainWindow()
                        
                            {
                        
                                this.InitializeComponent();
                        
                            }
                        
                        
                        
                            private async void Button_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                        
                        
                                TextBlock text = new() { Text = "Hello world" };
                        
                        
                        
                                TeachingTip teachingTip = new()
                        
                                {
                        
                                    Content = "This is a sample teaching tip.",
                        
                                    Title = "Sample Teaching Tip",
                        
                                    Target = text,
                        
                                    IsOpen = true,
                        
                                };
                        
                        
                        
                                CustomDialog dialog = new();
                        
                                dialog.Content = new StackPanel()
                        
                                {
                        
                                    Children =
                        
                                    {
                        
                                        text,
                        
                                        teachingTip
                        
                                    }
                        
                                };
                        
                        
                        
                                CustomDialogResult result = await dialog.ShowAsync();
                        
                            }
                        
                        }
                        
                        ```
                        
                        
                        
                        **NOTE:**
                        
                        
                        
                        I'm using the [WinUIEx](https://github.com/dotMorten/WinUIEx) NuGet package here but you should be able to do this without it.
                        
                
             
            
                
                    
                        Since it seems that it's a bit difficult to do this with the `ContentDialog`, let me show you another way that should be something close to what you are looking for:
                        
                        
                        
                        **CustomDialog.cs**
                        
                        ```cs
                        
                        using Microsoft.UI.Xaml;
                        
                        using System.Threading.Tasks;
                        
                        using WinUIEx;
                        
                        
                        
                        namespace App1;
                        
                        
                        
                        public enum CustomDialogResult
                        
                        {
                        
                            Cancel,
                        
                            OK,
                        
                        }
                        
                        
                        
                        public partial class CustomDialog : WindowEx
                        
                        {
                        
                            private TaskCompletionSource<CustomDialogResult>? _taskCompletionSource;
                        
                        
                        
                            public CustomDialog()
                        
                            {
                        
                                this.InitializeComponent();
                        
                                this.IsAlwaysOnTop = true;
                        
                                this.CenterOnScreen();
                        
                                this.SetWindowStyle(WindowStyle.Caption);
                        
                            }
                        
                            public new object? Content { get; set; }
                        
                        
                        
                            public Task<CustomDialogResult> ShowAsync()
                        
                            {
                        
                                this.ContentPresenter.Content = Content;
                        
                                _taskCompletionSource = new();
                        
                                this.Activate();
                        
                                return _taskCompletionSource.Task;
                        
                            }
                        
                        
                        
                            private void OKButton_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                                _taskCompletionSource?.SetResult(CustomDialogResult.OK);
                        
                                this.Close();
                        
                            }
                        
                        
                        
                            private void CancelButton_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                                _taskCompletionSource?.SetResult(CustomDialogResult.Cancel);
                        
                                this.Close();
                        
                            }
                        
                        }
                        
                        ```
                        
                        
                        
                        **CustomDialog.xaml.cs**
                        
                        ```xaml
                        
                        <ex:WindowEx
                        
                            x:Class="App1.CustomDialog"
                        
                            xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
                        
                            xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
                        
                            xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
                        
                            xmlns:ex="using:WinUIEx"
                        
                            xmlns:local="using:App1"
                        
                            xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
                        
                            Width="300"
                        
                            Height="200"
                        
                            mc:Ignorable="d">
                        
                        
                        
                            <Grid
                        
                                RowDefinitions="*,Auto">
                        
                                <ContentPresenter
                        
                                    x:Name="ContentPresenter"
                        
                                    Grid.Row="0" />
                        
                                <Grid
                        
                                    Grid.Row="1"
                        
                                    ColumnDefinitions="*,*">
                        
                                    <Button
                        
                                        Grid.Column="0"
                        
                                        Click="OKButton_Click"
                        
                                        Content="OK" />
                        
                                    <Button
                        
                                        Grid.Column="1"
                        
                                        Click="CancelButton_Click"
                        
                                        Content="Cancel" />
                        
                                </Grid>
                        
                            </Grid>
                        
                        </ex:WindowEx>
                        
                        ```
                        
                        
                        
                        and use it like this:
                        
                        
                        
                        ```cs
                        
                        public sealed partial class MainWindow : Window
                        
                        {
                        
                            public MainWindow()
                        
                            {
                        
                                this.InitializeComponent();
                        
                            }
                        
                        
                        
                            private CustomDialog? CustomDialog { get; set; }
                        
                        
                        
                            private async void Button_Click(object sender, RoutedEventArgs e)
                        
                            {
                        
                                CustomDialog = new()
                        
                                {
                        
                                    Title = "Title",
                        
                                    Content = "Are you ready?",
                        
                                };
                        
                        
                        
                                this.RootGrid.PointerPressed += RootGrid_PointerPressed;
                        
                                CustomDialogResult result = await CustomDialog.ShowAsync();
                        
                                this.RootGrid.PointerPressed -= RootGrid_PointerPressed;
                        
                                
                        
                                (sender as Button)!.Content = result.ToString();
                        
                        
                        
                            }
                        
                        
                        
                            private void RootGrid_PointerPressed(object sender, Microsoft.UI.Xaml.Input.PointerRoutedEventArgs e)
                        
                            {
                        
                                CustomDialog?.Close();
                        
                            }
                        
                        }
                        
                        ```
                        
                        
                        
                        The code above should have some missing features, but I hope it gives you some direction.
                        
                        
                        
                        **NOTE:**
                        
                        
                        
                        I'm using the [WinUIEx](https://github.com/dotMorten/WinUIEx) NuGet package here but you should be able to do this without it.