diff --git a/src/App.axaml b/src/App.axaml
index 7c9b12d..f568dc0 100644
--- a/src/App.axaml
+++ b/src/App.axaml
@@ -100,6 +100,9 @@
         <DataTemplate DataType="{x:Type viewModels:WarningViewModel}">
             <views:WarningView/>
         </DataTemplate>
+        <DataTemplate DataType="{x:Type viewModels:ShutdownCheckViewModel}">
+            <views:ShutdownCheckView/>
+        </DataTemplate>
     </Application.DataTemplates>
     <Application.Resources>
         <ResourceDictionary>
diff --git a/src/Interfaces/ICanCheckShutdown.cs b/src/Interfaces/ICanCheckShutdown.cs
new file mode 100644
index 0000000..ecc9e03
--- /dev/null
+++ b/src/Interfaces/ICanCheckShutdown.cs
@@ -0,0 +1,8 @@
+using System.Threading.Tasks;
+
+namespace MayShow.Interfaces;
+
+interface ICanCheckShutdown
+{
+    Task<bool> CheckIsSafeToShutdown();
+}
\ No newline at end of file
diff --git a/src/Interfaces/IChangeViewModel.cs b/src/Interfaces/IChangeViewModel.cs
index d992335..059e810 100644
--- a/src/Interfaces/IChangeViewModel.cs
+++ b/src/Interfaces/IChangeViewModel.cs
@@ -1,10 +1,9 @@
 using MayShow.ViewModels;
 
-namespace MayShow.Interfaces
+namespace MayShow.Interfaces;
+
+interface IChangeViewModel
 {
-    interface IChangeViewModel
-    {
-        void PushViewModel(BaseViewModel model);
-        void PopViewModel();
-    }
+    void PushViewModel(BaseViewModel model);
+    void PopViewModel();
 }
\ No newline at end of file
diff --git a/src/Interfaces/ITopLevelGrabber.cs b/src/Interfaces/ITopLevelGrabber.cs
index 9624d49..d58e1c5 100644
--- a/src/Interfaces/ITopLevelGrabber.cs
+++ b/src/Interfaces/ITopLevelGrabber.cs
@@ -1,9 +1,8 @@
 using Avalonia.Controls;
 
-namespace MayShow.Interfaces
+namespace MayShow.Interfaces;
+
+interface ITopLevelGrabber
 {
-    interface ITopLevelGrabber
-    {
-        TopLevel GetTopLevel();
-    }
+    TopLevel GetTopLevel();
 }
\ No newline at end of file
diff --git a/src/MainWindow.axaml b/src/MainWindow.axaml
index dfe33db..3867d1d 100644
--- a/src/MainWindow.axaml
+++ b/src/MainWindow.axaml
@@ -13,7 +13,8 @@
         Height="650"
         MinHeight="550">
     <dialogHost:DialogHost CloseOnClickAway="False" 
-                           Identifier="DialogHost">
+                           Identifier="DialogHost"
+                           x:Name="WindowDialogHost">
         <dialogHost:DialogHost.DialogContent>
             <StackPanel/>
         </dialogHost:DialogHost.DialogContent>
diff --git a/src/MainWindow.axaml.cs b/src/MainWindow.axaml.cs
index 7ef7402..33f39fc 100644
--- a/src/MainWindow.axaml.cs
+++ b/src/MainWindow.axaml.cs
@@ -1,4 +1,9 @@
+using System;
+using System.Threading.Tasks;
+using Avalonia;
 using Avalonia.Controls;
+using Avalonia.Controls.ApplicationLifetimes;
+using DialogHostAvalonia;
 using MayShow.Interfaces;
 using MayShow.ViewModels;
 
@@ -10,6 +15,60 @@ public partial class MainWindow : Window, ITopLevelGrabber
     {
         InitializeComponent();
         DataContext = new MainWindowViewModel(this);
+
+        Closing += WindowIsClosing;
+
+        var lifetime = Application.Current?.ApplicationLifetime as IClassicDesktopStyleApplicationLifetime;
+        // lifetime?.ShutdownRequested += ApplicationIsShuttingDown;
+    }
+
+    private async void WindowIsClosing(object? sender, WindowClosingEventArgs e)
+    {
+        e.Cancel = true; // async -> need to cancel immediately
+        if (await CheckIfClosePossible())
+        {
+            Closing -= WindowIsClosing;
+            var lifetime = Application.Current?.ApplicationLifetime as IClassicDesktopStyleApplicationLifetime;
+            lifetime?.ShutdownRequested -= ApplicationIsShuttingDown;
+            Close();
+        }
+    }
+
+    private async void ApplicationIsShuttingDown(object? sender, ShutdownRequestedEventArgs e)
+    {
+        e.Cancel = true; // async -> need to cancel immediately
+        if (await CheckIfClosePossible())
+        {
+            Closing -= WindowIsClosing;
+            var lifetime = Application.Current?.ApplicationLifetime as IClassicDesktopStyleApplicationLifetime;
+            lifetime?.ShutdownRequested -= ApplicationIsShuttingDown;
+            lifetime?.TryShutdown();
+        }
+    }
+
+    private async Task<bool> CheckIfClosePossible()
+    {
+        var canShutdown = true;
+        if (DataContext is MainWindowViewModel mwvm)
+        {
+            if (mwvm is ICanCheckShutdown canCheck)
+            {
+                canShutdown = await canCheck.CheckIsSafeToShutdown();
+            }
+            // only checking 1 level but for this app that is OK
+            if (canShutdown && mwvm.CurrentViewModel is ICanCheckShutdown currModel)
+            {
+                try
+                {
+                    canShutdown = await currModel.CheckIsSafeToShutdown();
+                }
+                catch (Exception)
+                {
+                    canShutdown = true;
+                }
+            }
+        }
+        return canShutdown;
     }
 
     public TopLevel GetTopLevel()
diff --git a/src/Models/Settings.cs b/src/Models/Settings.cs
index a627682..7989f37 100644
--- a/src/Models/Settings.cs
+++ b/src/Models/Settings.cs
@@ -34,7 +34,7 @@ class Settings : ChangeNotifier
     {
         var path = Path.Combine(
             Environment.GetFolderPath(Environment.SpecialFolder.ApplicationData),
-            "ReceiptPDFBuilder" // legacy name for existing settings prior to app name change
+            "MayShow"
         );
         if (!Directory.Exists(path))
         {
diff --git a/src/Models/ShutdownCheckOptions.cs b/src/Models/ShutdownCheckOptions.cs
new file mode 100644
index 0000000..e76b488
--- /dev/null
+++ b/src/Models/ShutdownCheckOptions.cs
@@ -0,0 +1,8 @@
+namespace MayShow.Models;
+
+enum ShutdownCheckOptions
+{
+    SaveAndShutdown,
+    NoSaveShutdown,
+    CancelShutdown,
+}
\ No newline at end of file
diff --git a/src/ViewModels/MainViewModel.cs b/src/ViewModels/MainViewModel.cs
index 600baaf..6105d04 100644
--- a/src/ViewModels/MainViewModel.cs
+++ b/src/ViewModels/MainViewModel.cs
@@ -23,8 +23,9 @@ using MayShows.Helpers;
 
 namespace MayShow.ViewModels;
 
-class MainViewModel : BaseViewModel, IFontResolver
+class MainViewModel : BaseViewModel, IFontResolver, ICanCheckShutdown
 {
+    private bool _isPerformingInitialLoad;
     private string _processDir;
     private bool _isCreatingPDF;
     private string _createPDFLog;
@@ -36,8 +37,11 @@ class MainViewModel : BaseViewModel, IFontResolver
 
     private Settings _settings;
 
+    private bool _hasUnsavedWork;
+
     public MainViewModel(IChangeViewModel viewModelChanger) : base(viewModelChanger)
     {
+        _isPerformingInitialLoad = true;
         _processDir = Path.GetDirectoryName(Environment.ProcessPath) ?? "";
         Console.WriteLine("Process is running from: {0}", _processDir);
         _isCreatingPDF = false;
@@ -47,7 +51,7 @@ class MainViewModel : BaseViewModel, IFontResolver
         _createPDFLog = "----- MayShow v" + Constants.AppVersion + " ------" + Environment.NewLine;
         _createPDFLog += quotes[quoteIndex] + Environment.NewLine;
         _createPDFLog += "---------------------------------------" + Environment.NewLine;
-        _createPDFLog += "Ready to create PDF!";
+        _createPDFLog += "Loaded and ready to create report!";
         _workingFolder = "";
         _reportFiles = new ObservableCollection<ReportFile>();
         _reportFiles.CollectionChanged += ( sender, e ) => { NotifyPropertyChanged(nameof(IsCreatePDFButtonEnabled)); };
@@ -59,12 +63,24 @@ class MainViewModel : BaseViewModel, IFontResolver
             LogInfo("Loading data at last used path of {0}", _settings.LastUsedPath);
             ScanFolder(_settings.LastUsedPath);
         }
+        else
+        {
+            LogInfo("Choose a receipt folder to begin...");
+        }
+        HasUnsavedWork = false;
+        _isPerformingInitialLoad = false;
     }
 
     public string ReportTitle
     {
         get => _reportTitle;
-        set { _reportTitle = value; NotifyPropertyChanged(); NotifyPropertyChanged(nameof(IsTitleBoxVisible)); }
+        set 
+        { 
+            _reportTitle = value;
+            NotifyPropertyChanged(); 
+            NotifyPropertyChanged(nameof(IsTitleBoxVisible)); 
+            NotifyPropertyChanged(nameof(CanAddItem)); 
+        }
     }
 
     public bool IsTitleBoxVisible
@@ -72,6 +88,11 @@ class MainViewModel : BaseViewModel, IFontResolver
         get => !string.IsNullOrWhiteSpace(_workingFolder);
     }
 
+    public bool CanAddItem
+    {
+        get => IsTitleBoxVisible && !IsCreatingPDF;
+    }
+
     public bool IsCreatingPDF
     {
         get => _isCreatingPDF;
@@ -81,6 +102,7 @@ class MainViewModel : BaseViewModel, IFontResolver
             NotifyPropertyChanged();
             NotifyPropertyChanged(nameof(IsCreatePDFButtonEnabled)); 
             NotifyPropertyChanged(nameof(HasWorkingFolderAndNotMakingPDF));
+            NotifyPropertyChanged(nameof(CanAddItem)); 
         }
     }
 
@@ -117,6 +139,16 @@ class MainViewModel : BaseViewModel, IFontResolver
         set { _createPDFLog = value; NotifyPropertyChanged(); }
     }
 
+    public bool HasUnsavedWork
+    {
+        get => _hasUnsavedWork;
+        set
+        {
+            _hasUnsavedWork = value;
+            NotifyPropertyChanged();
+        }
+    }
+
     public ObservableCollection<ReportFile> ReportFiles
     {
         get => _reportFiles;
@@ -157,6 +189,7 @@ class MainViewModel : BaseViewModel, IFontResolver
                 _settings.LastUsedPath = folder.Path.LocalPath;
                 await _settings.SaveSettingsAsync();
                 ResortPDFItemsByDate();
+                HasUnsavedWork = true;
             }
         }
     }
@@ -167,6 +200,7 @@ class MainViewModel : BaseViewModel, IFontResolver
         {
             WorkingFolder = path;
             NotifyPropertyChanged(nameof(IsTitleBoxVisible));
+            NotifyPropertyChanged(nameof(CanAddItem)); 
             var reportFilePath = Path.Combine(path, GetReportSavedDataFileName());
             var successfullyLoadedPriorReport = false;
             if (File.Exists(reportFilePath))
@@ -195,7 +229,11 @@ class MainViewModel : BaseViewModel, IFontResolver
                 {
                     AddFileBasedOnPath(filePath);
                 }
-                ResortPDFItemsByDate();
+                if (!_isPerformingInitialLoad)
+                {
+                    ResortPDFItemsByDate();
+                }
+                HasUnsavedWork = true;
             }
         }
         else
@@ -221,6 +259,7 @@ class MainViewModel : BaseViewModel, IFontResolver
             if (idx != -1)
             {
                 ReportFiles.RemoveAt(idx);
+                HasUnsavedWork = true;
             }
         }
     }
@@ -236,18 +275,20 @@ class MainViewModel : BaseViewModel, IFontResolver
             file.Title = updatedData.Title;
             file.ReceiptDateTime = updatedData.ReceiptDateTime;
             file.Notes = updatedData.Notes;
+            HasUnsavedWork = true;
         }
     }
 
     private string[] GetAllowedFileExtensionPatterns()
     {
+        // update GetAllowedFileExtensionPatternsWithoutStar if this is edited
         return [ "*.png", "*.jpg", "*.jpeg", "*.gif", "*.bmp", "*.webp", "*.pdf", "*.heic", ];
     }
 
     private string[] GetAllowedFileExtensionPatternsWithoutStar()
     {
-        var list = GetAllowedFileExtensionPatterns();
-        return list.Select(x => x.Replace("*.", "")).ToArray();
+        // update GetAllowedFileExtensionPatterns if this is edited
+        return [ "png", "jpg", "jpeg", "gif", "bmp", "webp", "pdf", "heic", ];
     }
 
     public async void AddItem()
@@ -316,6 +357,7 @@ class MainViewModel : BaseViewModel, IFontResolver
                     Notes = "",
                     FilePath = filePath,
                 });
+                HasUnsavedWork = true;
             }
         }
     }
@@ -351,6 +393,7 @@ class MainViewModel : BaseViewModel, IFontResolver
             {
                 var file = files[0];
                 reportFile.FilePath = file.Path.LocalPath;
+                HasUnsavedWork = true;
             }
         }
     }
@@ -389,6 +432,7 @@ class MainViewModel : BaseViewModel, IFontResolver
     {
         LogInfo("Sorting report files list...");
         ReportFiles = new ObservableCollection<ReportFile>(ReportFiles.OrderBy(x => x.ReceiptDateTime));
+        HasUnsavedWork = true;
     }
 
     public async void BuildPDF()
@@ -423,7 +467,7 @@ class MainViewModel : BaseViewModel, IFontResolver
         }
     }
 
-    public async void SaveInterimReportInfo()
+    public async Task SaveInterimReportInfo()
     {
         var report = new PDFReport()
         {
@@ -447,6 +491,7 @@ class MainViewModel : BaseViewModel, IFontResolver
         var savePath = Path.Combine(_workingFolder, GetReportSavedDataFileName());
         await File.WriteAllTextAsync(savePath, json);
         LogInfo("Saved report information to {0}", savePath);
+        HasUnsavedWork = false;
     }
 
     private async Task CreateAndSaveReportObjectAfterReportCreation()
@@ -691,4 +736,33 @@ class MainViewModel : BaseViewModel, IFontResolver
         OpenFolderForFileInFileViewer(outputPDFFileName);
         IsCreatingPDF = false;
     }
+
+    public async Task<bool> CheckIsSafeToShutdown()
+    {
+        if (!HasUnsavedWork || string.IsNullOrWhiteSpace(WorkingFolder))
+        {
+            return true;
+        }
+        else
+        {
+            var result = await DialogHost.Show(new ShutdownCheckViewModel());
+            if (result != null && result is ShutdownCheckOptions opt)
+            {
+                if (opt == ShutdownCheckOptions.SaveAndShutdown)
+                {
+                    await SaveInterimReportInfo();
+                    return true;
+                }
+                else if (opt == ShutdownCheckOptions.NoSaveShutdown)
+                {
+                    return true;
+                }
+                else if (opt == ShutdownCheckOptions.CancelShutdown)
+                {
+                    return false;
+                }
+            }
+        }
+        return false;
+    }
 }
\ No newline at end of file
diff --git a/src/ViewModels/ShutdownCheckViewModel.cs b/src/ViewModels/ShutdownCheckViewModel.cs
new file mode 100644
index 0000000..a823ecd
--- /dev/null
+++ b/src/ViewModels/ShutdownCheckViewModel.cs
@@ -0,0 +1,29 @@
+#nullable enable
+
+using DialogHostAvalonia;
+using MayShow.Models;
+
+namespace MayShow.ViewModels;
+
+class ShutdownCheckViewModel
+{
+
+    public ShutdownCheckViewModel()
+    {
+    }
+
+    public void SaveAndShutdown()
+    {
+        DialogHost.Close("DialogHost", ShutdownCheckOptions.SaveAndShutdown);
+    }
+
+    public void DoNotSaveAndShutdown()
+    {
+        DialogHost.Close("DialogHost", ShutdownCheckOptions.NoSaveShutdown);
+    }
+
+    public void CancelShutdown()
+    {
+        DialogHost.Close("DialogHost", ShutdownCheckOptions.CancelShutdown);
+    }
+}
\ No newline at end of file
diff --git a/src/Views/MainView.axaml b/src/Views/MainView.axaml
index 14f4134..e7ad9b5 100644
--- a/src/Views/MainView.axaml
+++ b/src/Views/MainView.axaml
@@ -223,7 +223,7 @@
         <StackPanel Orientation="Horizontal"
                     Spacing="4">
             <Button Command="{Binding AddItem}"
-                    IsEnabled="{Binding !IsCreatingPDF}">
+                    IsEnabled="{Binding CanAddItem}">
                 <TextBlock><Run Text="&#x002b;" FontFamily="{StaticResource FontAwesomeSolid}"/> Add Item(s)</TextBlock>
             </Button>
             <Button Command="{Binding SaveInterimReportInfo}"
diff --git a/src/Views/MainView.axaml.cs b/src/Views/MainView.axaml.cs
index 17a093e..b257af3 100644
--- a/src/Views/MainView.axaml.cs
+++ b/src/Views/MainView.axaml.cs
@@ -3,6 +3,7 @@ using Avalonia;
 using Avalonia.Controls;
 using Avalonia.Input;
 using Avalonia.Markup.Xaml;
+using MayShow.ViewModels;
 
 namespace MayShow.Views
 {
@@ -12,6 +13,7 @@ namespace MayShow.Views
         {
             this.InitializeComponent();
             LogBlock.PropertyChanged += LogBlock_PropertyChanged;
+            FilesGrid.CellEditEnded += FileCellEditEnded;
         }
 
         private void LogBlock_PropertyChanged(object? sender, AvaloniaPropertyChangedEventArgs e)
@@ -26,6 +28,18 @@ namespace MayShow.Views
         {
             var topLevel = TopLevel.GetTopLevel(this);
             topLevel?.FocusManager?.ClearFocus();
+            if (DataContext is MainViewModel mvm)
+            {
+                mvm?.HasUnsavedWork = true;
+            }
+        }
+
+        private void FileCellEditEnded(object? sender, DataGridCellEditEndedEventArgs args)
+        {
+            if (args.EditAction == DataGridEditAction.Commit && DataContext is MainViewModel mvm)
+            {
+                mvm?.HasUnsavedWork = true;
+            }
         }
     }
 }
diff --git a/src/Views/ShutdownCheckView.axaml b/src/Views/ShutdownCheckView.axaml
new file mode 100644
index 0000000..8f929ed
--- /dev/null
+++ b/src/Views/ShutdownCheckView.axaml
@@ -0,0 +1,39 @@
+<UserControl xmlns="https://github.com/avaloniaui"
+             xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
+             xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
+             xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+             mc:Ignorable="d" d:DesignWidth="800" d:DesignHeight="450"
+             x:Class="MayShow.Views.ShutdownCheckView"
+             xmlns:models="clr-namespace:MayShow.Models"
+             xmlns:vm="clr-namespace:MayShow.ViewModels"
+             xmlns:dialogHost="clr-namespace:DialogHostAvalonia;assembly=DialogHost.Avalonia"
+             x:DataType="vm:ShutdownCheckViewModel">
+    <StackPanel Orientation="Vertical"
+                Spacing="4">
+        <TextBlock TextAlignment="Center"
+                   FontWeight="Bold"
+                   FontSize="18"
+                   Text="Warning: You have unsaved report data!"/>
+        <TextBlock TextAlignment="Center"
+                   FontWeight="Bold"
+                   TextWrapping="Wrap"
+                   FontSize="14"
+                   Text="Do you want to save your data before the program is closed?"/>
+        <StackPanel Orientation="Horizontal"
+                    Spacing="8">
+            <Button Command="{Binding SaveAndShutdown}"
+                    Classes="accent"
+                    Content="Save Data and Close"
+                    HorizontalAlignment="Right"
+                    Margin="0,4,0,4"/>
+            <Button Command="{Binding DoNotSaveAndShutdown}"
+                    Content="Do NOT Save Data and Close"
+                    HorizontalAlignment="Right"
+                    Margin="0,4,0,4"/>
+            <Button Command="{Binding CancelShutdown}"
+                    Content="Cancel Program Shutdown"
+                    HorizontalAlignment="Right"
+                    Margin="0,4,0,4"/>
+        </StackPanel>
+    </StackPanel>
+</UserControl>
diff --git a/src/Views/ShutdownCheckView.axaml.cs b/src/Views/ShutdownCheckView.axaml.cs
new file mode 100644
index 0000000..bf871e7
--- /dev/null
+++ b/src/Views/ShutdownCheckView.axaml.cs
@@ -0,0 +1,14 @@
+using System;
+using Avalonia;
+using Avalonia.Controls;
+using Avalonia.Markup.Xaml;
+
+namespace MayShow.Views;
+
+public partial class ShutdownCheckView : UserControl
+{
+    public ShutdownCheckView()
+    {
+        this.InitializeComponent();
+    }
+}