diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Dock/DockViewModel.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Dock/DockViewModel.cs
index 95aa493d01..e1e306345e 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Dock/DockViewModel.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Dock/DockViewModel.cs
@@ -166,6 +166,13 @@ public enum DockPinSide
     End,
 }
 
+public enum ShowLabelsOption
+{
+    Default,
+    ShowLabels,
+    HideLabels,
+}
+
 // public class DockSettingsViewModel : ObservableObject
 // {
 //     private readonly DockSettings _settingsModel;
@@ -188,6 +195,8 @@ public partial class DockBandSettingsViewModel : ObservableObject
         {
             // TODO! we should have a way of saying "pinned from {extension}" vs
             // just a band that's from an extension
+            //
+            // TODO! add the number of items in the band
             return $"{_adapter.ExtensionName}";
         }
     }
@@ -196,10 +205,37 @@ public partial class DockBandSettingsViewModel : ObservableObject
 
     public IconInfoViewModel Icon => _adapter.IconViewModel;
 
-    public bool ShowLabels
+    public ShowLabelsOption ShowLabels
     {
-        get => _dockSettingsModel.ShowLabels ?? true; // TODO! deal with the fact it might be null
-        set => _dockSettingsModel.ShowLabels = value; // TODO! save settings
+        get
+        {
+            if (_dockSettingsModel.ShowLabels == null)
+            {
+                return ShowLabelsOption.Default;
+            }
+
+            return _dockSettingsModel.ShowLabels.Value ? ShowLabelsOption.ShowLabels : ShowLabelsOption.HideLabels;
+        }
+
+        set
+        {
+            _dockSettingsModel.ShowLabels = value switch
+            {
+                ShowLabelsOption.Default => null,
+                ShowLabelsOption.ShowLabels => true,
+                ShowLabelsOption.HideLabels => false,
+                _ => null,
+            };
+
+            // TODO! save settings
+        }
+    }
+
+    // used to map to ComboBox selection
+    public int ShowLabelsIndex
+    {
+        get => (int)ShowLabels;
+        set => ShowLabels = (ShowLabelsOption)value;
     }
 
     [ObservableProperty]
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Settings/DockSettings.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Settings/DockSettings.cs
index 0c4f1d9be4..f23d2060da 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Settings/DockSettings.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/Settings/DockSettings.cs
@@ -23,6 +23,8 @@ public class DockSettings
     public List<DockBandSettings> StartBands { get; set; } = [];
 
     public List<DockBandSettings> EndBands { get; set; } = [];
+
+    public bool ShowLabels { get; set; } = true;
 }
 
 public class DockBandSettings
@@ -30,6 +32,8 @@ public class DockBandSettings
     public string Id { get; set; } = string.Empty;
 
     public bool? ShowLabels { get; set; }
+
+    public bool ResolveShowLabels(bool defaultValue) => ShowLabels ?? defaultValue;
 }
 
 public enum DockSide
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/SettingsViewModel.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/SettingsViewModel.cs
index b7b10f231b..9b590c9ecd 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/SettingsViewModel.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI.ViewModels/SettingsViewModel.cs
@@ -168,6 +168,16 @@ public partial class SettingsViewModel : INotifyPropertyChanged
         }
     }
 
+    public bool Dock_ShowLabels
+    {
+        get => _settings.DockSettings.ShowLabels;
+        set
+        {
+            _settings.DockSettings.ShowLabels = value;
+            Save();
+        }
+    }
+
     public bool EnableDock
     {
         get => _settings.EnableDock;
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml b/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml
index d3d8190b9a..d0a278e1cf 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml
@@ -88,6 +88,19 @@
                         </ComboBox>
                     </controls:SettingsCard>
 
+                    <!--  Show Labels  -->
+                    <controls:SettingsCard Header="Show Labels">
+                        <controls:SettingsCard.Description>
+                            Choose whether to show labels for dock items by default.
+                        </controls:SettingsCard.Description>
+
+                        <ToggleSwitch
+                            IsOn="{x:Bind ShowLabels, Mode=TwoWay}"
+                            OffContent="Hide labels"
+                            OnContent="Show Labels" />
+
+                    </controls:SettingsCard>
+
                     <!--  Bands Section  -->
                     <TextBlock x:Uid="DockBandsSettingsHeader" Style="{StaticResource SettingsSectionHeaderTextBlockStyle}" />
 
@@ -133,10 +146,11 @@
                                                 </StackPanel>
                                             </ComboBoxItem>
                                         </ComboBox>
-                                        <ToggleSwitch
-                                            IsOn="{x:Bind ShowLabels, Mode=TwoWay}"
-                                            OffContent="Hide labels"
-                                            OnContent="Show Labels" />
+                                        <ComboBox MinWidth="120" SelectedIndex="{x:Bind ShowLabelsIndex, Mode=TwoWay}">
+                                            <ComboBoxItem Content="Default" />
+                                            <ComboBoxItem Content="Show Labels" />
+                                            <ComboBoxItem Content="Hide Labels" />
+                                        </ComboBox>
                                     </StackPanel>
                                 </controls:SettingsCard>
                             </DataTemplate>
diff --git a/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml.cs b/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml.cs
index ac2b165349..032e060d41 100644
--- a/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml.cs
+++ b/src/modules/cmdpal/Microsoft.CmdPal.UI/Settings/DockSettingsPage.xaml.cs
@@ -56,6 +56,12 @@ public sealed partial class DockSettingsPage : Page
         set => viewModel.Dock_Backdrop = SelectedIndexToBackdrop(value);
     }
 
+    public bool ShowLabels
+    {
+        get => viewModel.Dock_ShowLabels;
+        set => viewModel.Dock_ShowLabels = value;
+    }
+
     // Conversion methods for ComboBox bindings
     private static int DockSizeToSelectedIndex(DockSize size) => size switch
     {