diff --git a/Microsoft.Toolkit.Uwp.SampleApp/Data/DataGridDataItem.cs b/Microsoft.Toolkit.Uwp.SampleApp/Data/DataGridDataItem.cs
index f3d0bae93f2..c4b95f29e6a 100644
--- a/Microsoft.Toolkit.Uwp.SampleApp/Data/DataGridDataItem.cs
+++ b/Microsoft.Toolkit.Uwp.SampleApp/Data/DataGridDataItem.cs
@@ -152,6 +152,8 @@ public string Parent_mountain
         // You need to use DateTimeOffset to get proper binding to the CalendarDatePicker control, DateTime won't work.
         public DateTimeOffset First_ascent { get; set; }
 
+        public bool IsFavorite { get; set; }
+
         public string Ascents { get; set; }
 
         bool INotifyDataErrorInfo.HasErrors
diff --git a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/DataGrid/DataGridCode.bind b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/DataGrid/DataGridCode.bind
index 874762b3798..a0755a1225f 100644
--- a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/DataGrid/DataGridCode.bind
+++ b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/DataGrid/DataGridCode.bind
@@ -85,6 +85,7 @@
         <controls:DataGridTextColumn Header="Rank" Binding="{Binding Rank}" Tag="Rank" />
         <controls:DataGridComboBoxColumn Header="Mountain" Binding="{Binding Mountain}" Tag="Mountain" />
         <controls:DataGridTextColumn Header="Height (m)" Binding="{Binding Height_m}" Tag="Height_m" />
+        <controls:DataGridCheckBoxColumn Header="Favorite status" Binding="{Binding IsFavorite, Mode=TwoWay}" />
         <controls:DataGridTextColumn Header="Range" Binding="{Binding Range}" Tag="Range" />
         <controls:DataGridTextColumn Header="Parent Mountain" Binding="{Binding Parent_mountain}" Tag="Parent_mountain" />
         <controls:DataGridTemplateColumn Header="First Ascent" Tag="First_ascent">
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls.DataGrid/DataGrid/DataGrid.cs b/Microsoft.Toolkit.Uwp.UI.Controls.DataGrid/DataGrid/DataGrid.cs
index fcff002c18c..d6cba4d8cc8 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls.DataGrid/DataGrid/DataGrid.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls.DataGrid/DataGrid/DataGrid.cs
@@ -5727,16 +5727,39 @@ private void DataGrid_LostFocus(object sender, RoutedEventArgs e)
             _focusedObject = null;
             if (this.ContainsFocus)
             {
-                bool focusLeftDataGrid = true;
-                bool dataGridWillReceiveRoutedEvent = true;
-                DataGridColumn editingColumn = null;
-
-                // Walk up the visual tree of the newly focused element
-                // to determine if focus is still within DataGrid.
                 object focusedObject = GetFocusedElement();
                 DependencyObject focusedDependencyObject = focusedObject as DependencyObject;
 
-                while (focusedDependencyObject != null)
+                // Interacting with a Popup should never cause
+                // DataGrid to commit row/cell edits
+                bool focusLeftDataGrid = focusedDependencyObject is not Popup;
+                bool editingElementFocused = false;
+
+                if (this.EditingRow != null && this.EditingColumnIndex != -1)
+                {
+                    var editingColumn = this.ColumnsItemsInternal[this.EditingColumnIndex];
+                    var editingElement = editingColumn.GetCellContent(this.EditingRow);
+
+                    // Handle weird scenario for ComboBox and other ItemsControls
+                    // that don't work with DependencyObject.ContainsChild( )
+                    if (editingElement is not ItemsControl ic)
+                    {
+                        editingElementFocused = editingElement.ContainsChild(focusedDependencyObject);
+                    }
+                    else
+                    {
+                        editingElementFocused = ic.ItemsPanelRoot.ContainsChild(focusedDependencyObject);
+                    }
+
+                    if (editingElement == focusedDependencyObject)
+                    {
+                        focusLeftDataGrid = false;
+                    }
+                }
+
+                // Walk up the visual tree of the newly focused element
+                // to determine if focus is still within DataGrid.
+                while (focusedDependencyObject != null && focusedDependencyObject is not Popup && focusLeftDataGrid && !editingElementFocused)
                 {
                     if (focusedDependencyObject == this)
                     {
@@ -5744,11 +5767,11 @@ private void DataGrid_LostFocus(object sender, RoutedEventArgs e)
                         break;
                     }
 
-                    // Walk up the visual tree. Try using the framework element's
-                    // parent.  We do this because Popups behave differently with respect to the visual tree,
-                    // and it could have a parent even if the VisualTreeHelper doesn't find it.
-                    DependencyObject parent = null;
                     FrameworkElement element = focusedDependencyObject as FrameworkElement;
+
+                    // Walk up the visual tree. Try using the framework element's
+                    // parent.
+                    DependencyObject parent;
                     if (element == null)
                     {
                         parent = VisualTreeHelper.GetParent(focusedDependencyObject);
@@ -5760,32 +5783,19 @@ private void DataGrid_LostFocus(object sender, RoutedEventArgs e)
                         {
                             parent = VisualTreeHelper.GetParent(focusedDependencyObject);
                         }
-                        else
-                        {
-                            dataGridWillReceiveRoutedEvent = false;
-                        }
                     }
 
                     focusedDependencyObject = parent;
                 }
 
-                if (this.EditingRow != null && this.EditingColumnIndex != -1)
+                if (editingElementFocused)
                 {
-                    editingColumn = this.ColumnsItemsInternal[this.EditingColumnIndex];
-
-                    if (focusLeftDataGrid && editingColumn is DataGridTemplateColumn)
-                    {
-                        dataGridWillReceiveRoutedEvent = false;
-                    }
+                    HandleLostFocusForExternalElement(focusedObject);
                 }
-
-                if (focusLeftDataGrid && !(editingColumn is DataGridTemplateColumn))
+                else if (focusLeftDataGrid)
                 {
                     this.ContainsFocus = false;
-                    if (this.EditingRow != null)
-                    {
-                        CommitEdit(DataGridEditingUnit.Row, true /*exitEditingMode*/);
-                    }
+                    CommitEdit(DataGridEditingUnit.Row, true /*exitEditingMode*/);
 
                     ResetFocusedRow();
                     ApplyDisplayedRowsState(this.DisplayData.FirstScrollingSlot, this.DisplayData.LastScrollingSlot);
@@ -5798,14 +5808,15 @@ private void DataGrid_LostFocus(object sender, RoutedEventArgs e)
                         UpdateCurrentState(this.DisplayData.GetDisplayedElement(this.CurrentSlot), this.CurrentColumnIndex, true /*applyCellState*/);
                     }
                 }
-                else if (!dataGridWillReceiveRoutedEvent)
-                {
-                    FrameworkElement focusedElement = focusedObject as FrameworkElement;
-                    if (focusedElement != null)
-                    {
-                        focusedElement.LostFocus += new RoutedEventHandler(ExternalEditingElement_LostFocus);
-                    }
-                }
+            }
+        }
+
+        private void HandleLostFocusForExternalElement(object focusedObject)
+        {
+            FrameworkElement focusedElement = focusedObject as FrameworkElement;
+            if (focusedElement != null)
+            {
+                focusedElement.LostFocus += new RoutedEventHandler(ExternalEditingElement_LostFocus);
             }
         }
 
@@ -8643,12 +8654,6 @@ private bool UpdateStateOnTapped(TappedRoutedEventArgs args, int columnIndex, in
             {
                 _noSelectionChangeCount++;
 
-                beginEdit = allowEdit &&
-                            this.CurrentSlot == slot &&
-                            columnIndex != -1 &&
-                            (wasInEdit || this.CurrentColumnIndex == columnIndex) &&
-                            !GetColumnEffectiveReadOnlyState(this.ColumnsItemsInternal[columnIndex]);
-
                 DataGridSelectionAction action;
                 if (this.SelectionMode == DataGridSelectionMode.Extended && shift)
                 {
@@ -8687,6 +8692,12 @@ private bool UpdateStateOnTapped(TappedRoutedEventArgs args, int columnIndex, in
                 }
 
                 UpdateSelectionAndCurrency(columnIndex, slot, action, false /*scrollIntoView*/);
+
+                beginEdit = allowEdit &&
+                            this.CurrentSlot == slot &&
+                            columnIndex != -1 &&
+                            (wasInEdit || this.CurrentColumnIndex == columnIndex) &&
+                            !GetColumnEffectiveReadOnlyState(this.ColumnsItemsInternal[columnIndex]);
             }
             finally
             {