diff --git a/Trdo/Pages/SettingsPage.xaml b/Trdo/Pages/SettingsPage.xaml
index d1a31c0..edc234b 100644
--- a/Trdo/Pages/SettingsPage.xaml
+++ b/Trdo/Pages/SettingsPage.xaml
@@ -43,9 +43,52 @@
                     </Grid>
                 </StackPanel>
 
-                <!--  Enable Auto-Resume setting  -->
+                <!--  Play on startup setting  -->
                 <StackPanel Spacing="8">
-                    <TextBlock FontSize="16" Text="Enable Auto-Resume" />
+                    <TextBlock FontSize="16" Text="Play on startup" />
+                    <TextBlock
+                        FontSize="12"
+                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                        Text="Automatically start playing the last selected station when the app opens"
+                        TextWrapping="Wrap" />
+                    <InfoBar
+                        x:Name="AutoPlayWarningInfoBar"
+                        IsClosable="True"
+                        IsOpen="False"
+                        Message="This means audio will begin playing when Trdo is launched. It could be disruptive. Are you sure you want to enable this?"
+                        Severity="Warning">
+                        <InfoBar.ActionButton>
+                            <Button
+                                x:Name="ConfirmAutoPlayButton"
+                                Click="ConfirmAutoPlayButton_Click"
+                                Content="Enable anyway" />
+                        </InfoBar.ActionButton>
+                    </InfoBar>
+                    <Grid ColumnDefinitions="Auto,*" ColumnSpacing="12">
+                        <ToggleSwitch
+                            x:Name="AutoPlayOnStartupToggle"
+                            Toggled="AutoPlayOnStartupToggle_Toggled"
+                            Grid.Column="0"
+                            MinWidth="0"
+                            IsOn="{x:Bind ViewModel.IsAutoPlayOnStartupEnabled, Mode=OneWay}"
+                            OffContent=""
+                            OnContent="" />
+                        <TextBlock
+                            Grid.Column="1"
+                            VerticalAlignment="Center"
+                            FontSize="16"
+                            Text="{x:Bind ViewModel.AutoPlayOnStartupToggleText, Mode=OneWay}" />
+                    </Grid>
+                </StackPanel>
+
+                <!--  Auto-recover setting  -->
+                <StackPanel Spacing="8">
+                    <TextBlock FontSize="16" Text="Auto-recover" />
+                    <TextBlock
+                        FontSize="12"
+                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                        Text="If the stream is unstable or stops unexpectedly, Trdo will try to recover playback automatically"
+                        TextWrapping="Wrap" />
                     <Grid ColumnDefinitions="Auto,*" ColumnSpacing="12">
                         <ToggleSwitch
                             x:Name="WatchdogToggle"
diff --git a/Trdo/Pages/SettingsPage.xaml.cs b/Trdo/Pages/SettingsPage.xaml.cs
index f159cb9..4048468 100644
--- a/Trdo/Pages/SettingsPage.xaml.cs
+++ b/Trdo/Pages/SettingsPage.xaml.cs
@@ -13,6 +13,7 @@ public sealed partial class SettingsPage : Page
     private static extern nint GetActiveWindow();
 
     private float _displayLevel;
+    private bool _isUpdatingAutoPlayToggle;
 
     public SettingsViewModel ViewModel { get; }
 
@@ -133,4 +134,49 @@ private async void ExportButton_Click(object sender, RoutedEventArgs e)
             ImportExportInfoBar.IsOpen = true;
         }
     }
+
+    private void AutoPlayOnStartupToggle_Toggled(object sender, RoutedEventArgs e)
+    {
+        if (_isUpdatingAutoPlayToggle)
+        {
+            return;
+        }
+
+        bool isEnabled = ViewModel.IsAutoPlayOnStartupEnabled;
+        bool requestedState = AutoPlayOnStartupToggle.IsOn;
+
+        if (requestedState == isEnabled)
+        {
+            if (!requestedState)
+            {
+                AutoPlayWarningInfoBar.IsOpen = false;
+            }
+
+            return;
+        }
+
+        if (!requestedState)
+        {
+            ViewModel.IsAutoPlayOnStartupEnabled = false;
+            AutoPlayWarningInfoBar.IsOpen = false;
+            return;
+        }
+
+        SetAutoPlayToggle(false);
+        AutoPlayWarningInfoBar.IsOpen = true;
+    }
+
+    private void ConfirmAutoPlayButton_Click(object sender, RoutedEventArgs e)
+    {
+        ViewModel.IsAutoPlayOnStartupEnabled = true;
+        SetAutoPlayToggle(true);
+        AutoPlayWarningInfoBar.IsOpen = false;
+    }
+
+    private void SetAutoPlayToggle(bool value)
+    {
+        _isUpdatingAutoPlayToggle = true;
+        AutoPlayOnStartupToggle.IsOn = value;
+        _isUpdatingAutoPlayToggle = false;
+    }
 }
diff --git a/Trdo/Services/SettingsService.cs b/Trdo/Services/SettingsService.cs
index a16f265..b20bbca 100644
--- a/Trdo/Services/SettingsService.cs
+++ b/Trdo/Services/SettingsService.cs
@@ -9,6 +9,46 @@ public static class SettingsService
 {
     private const string IsFirstRunKey = "IsFirstRun";
     private const string IsVolumeSliderVisibleKey = "IsVolumeSliderVisible";
+    private const string AutoPlayOnStartupKey = "AutoPlayOnStartup";
+
+    /// <summary>
+    /// Gets or sets whether the app should automatically start playing the last selected station on startup.
+    /// Defaults to false when no saved value exists.
+    /// </summary>
+    public static bool AutoPlayOnStartup
+    {
+        get
+        {
+            try
+            {
+                if (ApplicationData.Current.LocalSettings.Values.TryGetValue(AutoPlayOnStartupKey, out object? value))
+                {
+                    return value switch
+                    {
+                        bool b => b,
+                        string s when bool.TryParse(s, out bool b2) => b2,
+                        _ => false
+                    };
+                }
+                return false;
+            }
+            catch
+            {
+                return false;
+            }
+        }
+        set
+        {
+            try
+            {
+                ApplicationData.Current.LocalSettings.Values[AutoPlayOnStartupKey] = value;
+            }
+            catch
+            {
+                // Silently fail if unable to save
+            }
+        }
+    }
 
     /// <summary>
     /// Gets or sets whether the volume slider is visible on the playing page.
diff --git a/Trdo/Services/WindowPlacementService.cs b/Trdo/Services/WindowPlacementService.cs
index 2c47938..10e7576 100644
--- a/Trdo/Services/WindowPlacementService.cs
+++ b/Trdo/Services/WindowPlacementService.cs
@@ -29,8 +29,11 @@ public static void PositionWindowNearAnchor(Window window, int width, int height
         int x = placeLeft ? anchor.X - width - WindowMargin : anchor.X + WindowMargin;
         int y = placeAbove ? anchor.Y - height - WindowMargin : anchor.Y + WindowMargin;
 
-        x = System.Math.Clamp(x, workArea.X, workArea.X + workArea.Width - width);
-        y = System.Math.Clamp(y, workArea.Y, workArea.Y + workArea.Height - height);
+        int maxX = System.Math.Max(workArea.X, workArea.X + workArea.Width - width);
+        int maxY = System.Math.Max(workArea.Y, workArea.Y + workArea.Height - height);
+
+        x = System.Math.Clamp(x, workArea.X, maxX);
+        y = System.Math.Clamp(y, workArea.Y, maxY);
 
         window.MoveAndResize(x, y, width, height);
     }
diff --git a/Trdo/ViewModels/PlayerViewModel.cs b/Trdo/ViewModels/PlayerViewModel.cs
index 53f21ff..614d335 100644
--- a/Trdo/ViewModels/PlayerViewModel.cs
+++ b/Trdo/ViewModels/PlayerViewModel.cs
@@ -108,6 +108,13 @@ public PlayerViewModel()
         {
             Debug.WriteLine($"[PlayerViewModel] Initializing stream with URL: {_selectedStation.StreamUrl}");
             InitializeStream(_selectedStation.StreamUrl);
+
+            // Auto-play on startup if the setting is enabled
+            if (SettingsService.AutoPlayOnStartup)
+            {
+                Debug.WriteLine("[PlayerViewModel] AutoPlayOnStartup is enabled, starting playback...");
+                _player.Play();
+            }
         }
         else
         {
diff --git a/Trdo/ViewModels/SettingsViewModel.cs b/Trdo/ViewModels/SettingsViewModel.cs
index 213852c..ac1ddb2 100644
--- a/Trdo/ViewModels/SettingsViewModel.cs
+++ b/Trdo/ViewModels/SettingsViewModel.cs
@@ -20,6 +20,7 @@ public partial class SettingsViewModel : INotifyPropertyChanged
     private string _startupToggleText = "Off";
     private string _watchdogToggleText = "Off";
     private string _autoBufferToggleText = "Off";
+    private string _autoPlayOnStartupToggleText = "Off";
     private StartupTask? _startupTask;
     private bool _initDone;
 
@@ -27,7 +28,7 @@ public partial class SettingsViewModel : INotifyPropertyChanged
 
     public SettingsViewModel()
     {
-        _playerViewModel = new PlayerViewModel();
+        _playerViewModel = PlayerViewModel.Shared;
 
         // Subscribe to PlayerViewModel property changes
         _playerViewModel.PropertyChanged += (_, args) =>
@@ -57,6 +58,7 @@ public SettingsViewModel()
         // Initialize toggle text
         WatchdogToggleText = GetToggleText(_playerViewModel.WatchdogEnabled);
         AutoBufferToggleText = GetToggleText(_playerViewModel.AutoBufferIncreaseEnabled);
+        AutoPlayOnStartupToggleText = GetToggleText(SettingsService.AutoPlayOnStartup);
 
         // Initialize startup task
         _ = InitializeStartupTaskAsync();
@@ -101,6 +103,32 @@ public string StartupToggleText
         }
     }
 
+    /// <summary>
+    /// Gets or sets whether the app should automatically start playing the last selected station on startup.
+    /// </summary>
+    public bool IsAutoPlayOnStartupEnabled
+    {
+        get => SettingsService.AutoPlayOnStartup;
+        set
+        {
+            if (value == SettingsService.AutoPlayOnStartup) return;
+            SettingsService.AutoPlayOnStartup = value;
+            OnPropertyChanged();
+            AutoPlayOnStartupToggleText = GetToggleText(value);
+        }
+    }
+
+    public string AutoPlayOnStartupToggleText
+    {
+        get => _autoPlayOnStartupToggleText;
+        set
+        {
+            if (value == _autoPlayOnStartupToggleText) return;
+            _autoPlayOnStartupToggleText = value;
+            OnPropertyChanged();
+        }
+    }
+
     public bool IsWatchdogEnabled
     {
         get => _playerViewModel.WatchdogEnabled;