diff --git a/src/modules/peek/Peek.UI/MainWindowViewModel.cs b/src/modules/peek/Peek.UI/MainWindowViewModel.cs
index ac46365f8b..3bd809630d 100644
--- a/src/modules/peek/Peek.UI/MainWindowViewModel.cs
+++ b/src/modules/peek/Peek.UI/MainWindowViewModel.cs
@@ -226,24 +226,36 @@ namespace Peek.UI
             OnPropertyChanged(nameof(DisplayItemCount));
 
             // Attempt the deletion then navigate to the next file.
-            DispatcherQueue.GetForCurrentThread().TryEnqueue(() =>
+            DispatcherQueue.GetForCurrentThread().TryEnqueue(async () =>
             {
-                Task.Delay(DeleteDelayMs);
+                await Task.Delay(DeleteDelayMs);
                 int result = DeleteFile(item, hwnd);
 
-                if (result != 0)
+                if (result == 0)
                 {
-                    // On failure, log the error, show a message in the UI, and reinstate the
-                    // deleted file if it still exists.
-                    DeleteErrorMessageHelper.LogError(result);
-                    ShowDeleteError(item.Name, result);
+                    // Success.
+                    return;
+                }
 
-                    if (File.Exists(item.Path))
+                if (result == ERROR_CANCELLED)
+                {
+                    if (Path.GetPathRoot(item.Path) is string root)
                     {
-                        _deletedItemIndexes.Remove(index);
-                        OnPropertyChanged(nameof(DisplayItemCount));
+                        var driveInfo = new DriveInfo(root);
+                        Logger.LogInfo($"User cancelled deletion of \"{item.Name}\" on " +
+                            $"{driveInfo.DriveType} drive.");
                     }
                 }
+                else
+                {
+                    // For failures other than user cancellation, log the error and show a message
+                    // in the UI.
+                    DeleteErrorMessageHelper.LogError(result);
+                    ShowDeleteError(item.Name, result);
+                }
+
+                // For all errors, reinstate the deleted file if it still exists.
+                ReinstateDeletedFile(item, index);
             });
 
             Navigate(_navigationDirection, isAfterDelete: true);
@@ -278,6 +290,15 @@ namespace Peek.UI
             return result;
         }
 
+        private void ReinstateDeletedFile(IFileSystemItem item, int index)
+        {
+            if (File.Exists(item.Path))
+            {
+                _deletedItemIndexes.Remove(index);
+                OnPropertyChanged(nameof(DisplayItemCount));
+            }
+        }
+
         /// <summary>
         /// Informs shell listeners like Explorer windows that a delete operation has occurred.
         /// </summary>
diff --git a/src/modules/peek/Peek.UI/Native/NativeMethods.cs b/src/modules/peek/Peek.UI/Native/NativeMethods.cs
index 1fe0035f3e..35040e1648 100644
--- a/src/modules/peek/Peek.UI/Native/NativeMethods.cs
+++ b/src/modules/peek/Peek.UI/Native/NativeMethods.cs
@@ -94,6 +94,11 @@ namespace Peek.UI.Native
         /// <remarks>Declared in shellapi.h./remarks>
         internal const ushort FOF_WANTNUKEWARNING = 0x4000;
 
+        /// <summary>
+        /// The user cancelled the delete operation. Not classified as an error for our purposes.
+        /// </summary>
+        internal const int ERROR_CANCELLED = 1223;
+
         /// <summary>
         /// Common error codes when calling SHFileOperation to delete a file.
         /// </summary>
diff --git a/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml b/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml
index 78879bc74c..539baf9471 100644
--- a/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml
+++ b/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml
@@ -69,7 +69,7 @@
             DefaultButton="Close">
             <StackPanel VerticalAlignment="Stretch" HorizontalAlignment="Stretch" Spacing="12">
                 <TextBlock x:Uid="DeleteConfirmationDialog_Message" TextWrapping="Wrap" />
-                <CheckBox x:Name="DeleteDontAskCheckbox" x:Uid="DeleteConfirmationDialog_DontAskCheckbox" />
+                <CheckBox x:Name="DeleteDontWarnCheckbox" x:Uid="DeleteConfirmationDialog_DontWarnCheckbox" />
             </StackPanel>
         </ContentDialog>
     </Grid>
diff --git a/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml.cs b/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml.cs
index 461ca227c1..5af4a7bce2 100644
--- a/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml.cs
+++ b/src/modules/peek/Peek.UI/PeekXAML/MainWindow.xaml.cs
@@ -86,8 +86,8 @@ namespace Peek.UI
                 {
                     if (await ShowDeleteConfirmationDialogAsync() == ContentDialogResult.Primary)
                     {
-                        // Delete after asking for confirmation. Persist the "Don't ask again" choice if set.
-                        ViewModel.DeleteItem(DeleteDontAskCheckbox.IsChecked, this.GetWindowHandle());
+                        // Delete after asking for confirmation. Persist the "Don't warn again" choice if set.
+                        ViewModel.DeleteItem(DeleteDontWarnCheckbox.IsChecked, this.GetWindowHandle());
                     }
                 }
                 else
@@ -104,8 +104,7 @@ namespace Peek.UI
 
         private async Task<ContentDialogResult> ShowDeleteConfirmationDialogAsync()
         {
-            DeleteDontAskCheckbox.IsChecked = false;
-
+            DeleteDontWarnCheckbox.IsChecked = false;
             DeleteConfirmationDialog.XamlRoot = Content.XamlRoot;
 
             return await DeleteConfirmationDialog.ShowAsync();
diff --git a/src/modules/peek/Peek.UI/Strings/en-us/Resources.resw b/src/modules/peek/Peek.UI/Strings/en-us/Resources.resw
index b24e866c87..4ffec5f685 100644
--- a/src/modules/peek/Peek.UI/Strings/en-us/Resources.resw
+++ b/src/modules/peek/Peek.UI/Strings/en-us/Resources.resw
@@ -369,7 +369,7 @@
   <data name="DeleteConfirmationDialog_Message.Text" xml:space="preserve">
     <value>Are you sure you want to delete this file?</value>
   </data>
-  <data name="DeleteConfirmationDialog_DontAskCheckbox.Content" xml:space="preserve">
+  <data name="DeleteConfirmationDialog_DontWarnCheckbox.Content" xml:space="preserve">
     <value>Don't show this warning again</value>
   </data>
 </root>
\ No newline at end of file