diff --git a/FluentFlyoutWPF/Pages/TaskbarWidgetPage.xaml b/FluentFlyoutWPF/Pages/TaskbarWidgetPage.xaml
index ebed25c8..a8731d2d 100644
--- a/FluentFlyoutWPF/Pages/TaskbarWidgetPage.xaml
+++ b/FluentFlyoutWPF/Pages/TaskbarWidgetPage.xaml
@@ -174,6 +174,30 @@
                             </controls:ToggleSwitch.Style>
                         </controls:ToggleSwitch>
                     </ui:CardControl>
+                    <ui:CardControl Icon="{ui:SymbolIcon ArrowFit20}" Margin="0,0,0,3">
+                        <ui:CardControl.Header>
+                            <StackPanel Orientation="Vertical">
+                                <TextBlock Text="{DynamicResource TaskbarWidgetPreventStartOverlapTitle}" FontSize="14" FontWeight="Regular" VerticalAlignment="Center" />
+                                <TextBlock Text="{DynamicResource TaskbarWidgetPreventStartOverlapDescription}" FontSize="12" Opacity="0.5" />
+                            </StackPanel>
+                        </ui:CardControl.Header>
+                        <controls:ToggleSwitch IsChecked="{Binding TaskbarWidgetPreventStartOverlap, Mode=TwoWay}">
+                            <controls:ToggleSwitch.Style>
+                                <Style TargetType="controls:ToggleSwitch" BasedOn="{StaticResource {x:Type controls:ToggleSwitch}}">
+                                    <Setter Property="IsEnabled" Value="False" />
+                                    <Style.Triggers>
+                                        <MultiDataTrigger>
+                                            <MultiDataTrigger.Conditions>
+                                                <Condition Binding="{Binding IsPremiumUnlocked}" Value="True" />
+                                                <Condition Binding="{Binding TaskbarWidgetPosition}" Value="0" />
+                                            </MultiDataTrigger.Conditions>
+                                            <Setter Property="IsEnabled" Value="True" />
+                                        </MultiDataTrigger>
+                                    </Style.Triggers>
+                                </Style>
+                            </controls:ToggleSwitch.Style>
+                        </controls:ToggleSwitch>
+                    </ui:CardControl>
                     <ui:CardControl Icon="{ui:SymbolIcon ArrowFit20}" Margin="0,0,0,0">
                         <ui:CardControl.Header>
                             <StackPanel Orientation="Vertical">
diff --git a/FluentFlyoutWPF/Resources/Localization/Dictionary-en-US.xaml b/FluentFlyoutWPF/Resources/Localization/Dictionary-en-US.xaml
index 2a43079a..367f7a00 100644
--- a/FluentFlyoutWPF/Resources/Localization/Dictionary-en-US.xaml
+++ b/FluentFlyoutWPF/Resources/Localization/Dictionary-en-US.xaml
@@ -56,6 +56,8 @@ hides repeat, shuffle and player info</System:String>
     <System:String x:Key="TaskbarWidgetPaddingSettingsDescription">Adjust the padding around the widget to fit your taskbar style</System:String>
     <System:String x:Key="TaskbarWidgetPaddingTitle">Automatic Padding for Windows Widgets button</System:String>
     <System:String x:Key="TaskbarWidgetPaddingDescription">Turn this feature on if you have Windows Widgets enabled</System:String>
+    <System:String x:Key="TaskbarWidgetPreventStartOverlapTitle">Prevent overlap with Start button</System:String>
+    <System:String x:Key="TaskbarWidgetPreventStartOverlapDescription">For left alignment, shrink widget width if space before Start is limited</System:String>
     <System:String x:Key="TaskbarWidgetManualPaddingTitle">Custom Padding</System:String>
     <System:String x:Key="TaskbarWidgetManualPaddingDescription">Add extra padding (default: 0px)</System:String>
     <System:String x:Key="TaskbarWidgetBackgroundBlurTitle">Background Blur</System:String>
diff --git a/FluentFlyoutWPF/ViewModels/UserSettings.cs b/FluentFlyoutWPF/ViewModels/UserSettings.cs
index 27544d98..25db0bfa 100644
--- a/FluentFlyoutWPF/ViewModels/UserSettings.cs
+++ b/FluentFlyoutWPF/ViewModels/UserSettings.cs
@@ -363,6 +363,13 @@ public string LockKeysDurationText
     [ObservableProperty]
     public partial bool TaskbarWidgetPadding { get; set; }
 
+    /// <summary>
+    /// Prevent overlap with the Start button by shrinking the taskbar widget width when there is not enough space.
+    /// Applies only when the widget position is set to left.
+    /// </summary>
+    [ObservableProperty]
+    public partial bool TaskbarWidgetPreventStartOverlap { get; set; }
+
     /// <summary>
     /// Manual padding value in pixels applied to the taskbar widget
     /// </summary>
@@ -623,6 +630,7 @@ public UserSettings()
         TaskbarWidgetSelectedMonitor = 0;
         TaskbarWidgetPosition = 0;
         TaskbarWidgetPadding = true;
+        TaskbarWidgetPreventStartOverlap = false;
         TaskbarWidgetManualPadding = 0;
         TaskbarWidgetBackgroundBlur = false;
         TaskbarWidgetHideCompletely = false;
@@ -720,6 +728,12 @@ partial void OnTaskbarWidgetManualPaddingChanged(int oldValue, int newValue)
         UpdateTaskbar();
     }
 
+    partial void OnTaskbarWidgetPreventStartOverlapChanged(bool oldValue, bool newValue)
+    {
+        if (oldValue == newValue || _initializing) return;
+        UpdateTaskbar();
+    }
+
     partial void OnTaskbarWidgetBackgroundBlurChanged(bool oldValue, bool newValue)
     {
         if (oldValue == newValue || _initializing) return;
diff --git a/FluentFlyoutWPF/Windows/TaskbarWindow.xaml.cs b/FluentFlyoutWPF/Windows/TaskbarWindow.xaml.cs
index de533297..df3e32e0 100644
--- a/FluentFlyoutWPF/Windows/TaskbarWindow.xaml.cs
+++ b/FluentFlyoutWPF/Windows/TaskbarWindow.xaml.cs
@@ -33,10 +33,13 @@ public partial class TaskbarWindow : Window
     private AutomationElement? _widgetElement;
     private AutomationElement? _trayElement;
     private AutomationElement? _taskbarFrameElement;
+    private AutomationElement? _startButtonElement;
+    private AutomationElement? _startButtonByNameElement;
     // reference to main window for flyout functions
     private MainWindow? _mainWindow;
     private int _lastSelectedMonitor = -1;
     private bool _positionUpdateInProgress;
+    private bool _startButtonLookupWarningLogged;
     private readonly Dictionary<string, Task> _pendingAutomationTasks = [];
     
     private GlobalSystemMediaTransportControlsSessionPlaybackStatus? _lastPlaybackStatus;
@@ -546,10 +549,44 @@ private Rect PositionWidget(IntPtr taskbarHandle, RECT taskbarRect, double dpiSc
 
         widgetLeft += SettingsManager.Current.TaskbarWidgetManualPadding;
 
+        int finalPhysicalWidth = physicalWidth;
+        if (SettingsManager.Current.TaskbarWidgetPosition == 0 && SettingsManager.Current.TaskbarWidgetPreventStartOverlap)
+        {
+            const int startButtonGap = 2;
+            (bool foundStartButton, Rect startButtonRect) = GetStartButtonRect(taskbarHandle);
+            bool hasValidStartBounds = foundStartButton &&
+                startButtonRect.Width > 0 &&
+                startButtonRect.Left > taskbarRect.Left &&
+                startButtonRect.Left < taskbarRect.Right &&
+                startButtonRect.Left < (taskbarRect.Left + taskbarRect.Right) / 2.0;
+
+            if (hasValidStartBounds)
+            {
+                _startButtonLookupWarningLogged = false;
+
+                int startLeftInTaskbar = (int)(startButtonRect.Left - taskbarRect.Left);
+                int noOverlapRightBoundary = startLeftInTaskbar - startButtonGap;
+
+                if (widgetLeft >= noOverlapRightBoundary)
+                    widgetLeft = Math.Max(0, noOverlapRightBoundary - 1);
+
+                int maxWidthToFitGap = noOverlapRightBoundary - widgetLeft;
+                if (maxWidthToFitGap < finalPhysicalWidth)
+                {
+                    finalPhysicalWidth = Math.Max(1, maxWidthToFitGap);
+                }
+            }
+            else if (!_startButtonLookupWarningLogged)
+            {
+                Logger.Warn("Failed to resolve Start button bounds for taskbar overlap prevention. Using existing widget width.");
+                _startButtonLookupWarningLogged = true;
+            }
+        }
+
         // Set widget position within canvas
         Canvas.SetLeft(Widget, widgetLeft / dpiScale);
         Canvas.SetTop(Widget, widgetTop / dpiScale);
-        Widget.Width = physicalWidth / dpiScale;
+        Widget.Width = finalPhysicalWidth / dpiScale;
         Widget.Height = physicalHeight / dpiScale;
 
         return new Rect(Canvas.GetLeft(Widget) * dpiScale, Canvas.GetTop(Widget) * dpiScale, Widget.Width * dpiScale, Widget.Height * dpiScale);
@@ -656,11 +693,14 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
         });
     }
 
-    private (bool, Rect) GetTaskbarXamlElementRect(IntPtr taskbarHandle, ref AutomationElement? elementCache, string elementName)
+    private (bool, Rect) GetTaskbarXamlElementRect(IntPtr taskbarHandle, ref AutomationElement? elementCache, string elementName, AutomationProperty? property = null)
     {
         if (taskbarHandle == IntPtr.Zero)
             return (false, Rect.Empty);
 
+        AutomationProperty lookupProperty = property ?? AutomationElement.AutomationIdProperty;
+        string pendingTaskKey = $"{lookupProperty.ProgrammaticName}:{elementName}";
+
         try
         {
             // reset if monitor changed
@@ -670,7 +710,7 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
             // find widget in XAML
             if (elementCache == null)
             {
-                if (_pendingAutomationTasks.TryGetValue(elementName, out var pendingTask) && !pendingTask.IsCompleted)
+                if (_pendingAutomationTasks.TryGetValue(pendingTaskKey, out var pendingTask) && !pendingTask.IsCompleted)
                     return (false, Rect.Empty);
 
                 AutomationElement? found = null;
@@ -678,9 +718,9 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
                 {
                     var root = AutomationElement.FromHandle(taskbarHandle);
                     found = root.FindFirst(TreeScope.Descendants,
-                        new PropertyCondition(AutomationElement.AutomationIdProperty, elementName));
+                        new PropertyCondition(lookupProperty, elementName));
                 });
-                _pendingAutomationTasks[elementName] = findTask;
+                _pendingAutomationTasks[pendingTaskKey] = findTask;
 
                 if (!findTask.Wait(1000))
                 {
@@ -698,7 +738,7 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
 
             try
             {
-                if (_pendingAutomationTasks.TryGetValue(elementName, out var pendingTask) && !pendingTask.IsCompleted)
+                if (_pendingAutomationTasks.TryGetValue(pendingTaskKey, out var pendingTask) && !pendingTask.IsCompleted)
                 {
                     elementCache = null;
                     return (false, Rect.Empty);
@@ -706,7 +746,7 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
 
                 var cachedElement = elementCache;
                 var boundsTask = Task.Run(() => cachedElement.Current.BoundingRectangle);
-                _pendingAutomationTasks[elementName] = boundsTask;
+                _pendingAutomationTasks[pendingTaskKey] = boundsTask;
 
                 if (!boundsTask.Wait(500))
                 {
@@ -773,4 +813,13 @@ public void UpdateUi(string title, string artist, BitmapImage? icon, GlobalSyste
     {
         return GetTaskbarXamlElementRect(taskbarHandle, ref _taskbarFrameElement, "TaskbarFrame");
     }
+
+    private (bool, Rect) GetStartButtonRect(IntPtr taskbarHandle)
+    {
+        (bool foundById, Rect startRect) = GetTaskbarXamlElementRect(taskbarHandle, ref _startButtonElement, "StartButton");
+        if (foundById)
+            return (true, startRect);
+
+        return GetTaskbarXamlElementRect(taskbarHandle, ref _startButtonByNameElement, "Start", AutomationElement.NameProperty);
+    }
 }
\ No newline at end of file