diff --git a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/SampleEmailDataType.cs b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/SampleEmailDataType.cs
index 0822836189d..3fc2a0eca62 100644
--- a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/SampleEmailDataType.cs
+++ b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/SampleEmailDataType.cs
@@ -8,7 +8,7 @@
 namespace Microsoft.Toolkit.Uwp.SampleApp.SamplePages
 {
     /// <summary>
-    /// Sample of strongly-typed email address simulated data for <see cref="TokenizingTextBox"/>.
+    /// Sample of strongly-typed email address simulated data for <see cref="Microsoft.Toolkit.Uwp.UI.Controls.TokenizingTextBox"/>.
     /// </summary>
     public class SampleEmailDataType
     {
diff --git a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxPage.xaml.cs b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxPage.xaml.cs
index 110c6518894..86bbd2121c0 100644
--- a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxPage.xaml.cs
+++ b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxPage.xaml.cs
@@ -83,6 +83,7 @@ public sealed partial class TokenizingTextBoxPage : Page, IXamlRenderListener
         private TokenizingTextBox _ttbEmail;
         private ListView _ttbEmailSuggestions;
         private Button _ttbEmailClear;
+        private Button _ttbEmailShowItems;
 
         private AdvancedCollectionView _acv;
         private AdvancedCollectionView _acvEmail;
@@ -117,9 +118,6 @@ public void OnXamlRendered(FrameworkElement control)
             if (control.FindChildByName("TokenBox") is TokenizingTextBox ttb)
             {
                 _ttb = ttb;
-
-                ////_ttb.ItemsSource = new ObservableCollection<SampleDataType>(); // TODO: This shouldn't be required, we should initialize in control constructor???
-
                 _ttb.TokenItemAdded += TokenItemAdded;
                 _ttb.TokenItemRemoving += TokenItemRemoved;
                 _ttb.TextChanged += TextChanged;
@@ -146,8 +144,7 @@ public void OnXamlRendered(FrameworkElement control)
                 _ttbEmail = ttbEmail;
 
                 _ttbEmail.ItemsSource = _selectedEmails;
-
-                // _ttbEmail.ItemClick += EmailTokenItemClick;
+                _ttbEmail.ItemClick += EmailTokenItemClick;
                 _ttbEmail.TokenItemAdding += EmailTokenItemAdding;
                 _ttbEmail.TokenItemAdded += EmailTokenItemAdded;
                 _ttbEmail.TokenItemRemoved += EmailTokenItemRemoved;
@@ -181,9 +178,19 @@ public void OnXamlRendered(FrameworkElement control)
             if (control.FindChildByName("ClearButton") is Button btn)
             {
                 _ttbEmailClear = btn;
-
                 _ttbEmailClear.Click += ClearButtonClick;
             }
+
+            if (_ttbEmailShowItems != null)
+            {
+                _ttbEmailShowItems.Click -= ShowButtonClick;
+            }
+
+            if (control.FindChildByName("ShowSelectedEmails") is Button showBtn)
+            {
+                _ttbEmailShowItems = showBtn;
+                _ttbEmailShowItems.Click += ShowButtonClick;
+            }
         }
 
         private async void EmailTokenItemClick(object sender, ItemClickEventArgs e)
@@ -316,6 +323,28 @@ private void ClearButtonClick(object sender, RoutedEventArgs e)
             _acvEmail.RefreshFilter();
         }
 
+        private async void ShowButtonClick(object sender, RoutedEventArgs e)
+        {
+            // Grab the list of items and identify which ones are free text, which ones are tokens
+            string message = string.Empty;
+
+            foreach (var item in _ttbEmail.Items)
+            {
+                if (!string.IsNullOrEmpty(message))
+                {
+                    message += "\r\n";
+                }
+
+                message += item is ITokenStringContainer ? "Unrslvd: " : "Token  : ";
+                var textVal = item.ToString();
+
+                message += string.IsNullOrEmpty(textVal) ? "<empty>" : textVal;
+            }
+
+            MessageDialog md = new MessageDialog(message, "Item List with type");
+            await md.ShowAsync();
+        }
+
         // Move to Email Suggest ListView list when we keydown from the TTB
         private void EmailPreviewKeyDown(object sender, KeyRoutedEventArgs e)
         {
diff --git a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxXaml.bind b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxXaml.bind
index fd6626519d3..54ccba3b621 100644
--- a/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxXaml.bind
+++ b/Microsoft.Toolkit.Uwp.SampleApp/SamplePages/TokenizingTextBox/TokenizingTextBoxXaml.bind
@@ -1,8 +1,9 @@
 <Page xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation"
       xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
-      xmlns:controls="using:Microsoft.Toolkit.Uwp.UI.Controls"
       xmlns:d="http://schemas.microsoft.com/expression/blend/2008"
       xmlns:mc="http://schemas.openxmlformats.org/markup-compatibility/2006"
+      xmlns:controls="using:Microsoft.Toolkit.Uwp.UI.Controls"
+      xmlns:ex="using:Microsoft.Toolkit.Uwp.UI.Extensions"
       mc:Ignorable="d">
 
   <Grid Margin="40,40,40,40">
@@ -15,7 +16,7 @@
       <controls:TokenizingTextBox
           x:Name="TokenBox"
           PlaceholderText="Add Actions"
-          QueryIcon="Setting"
+          QueryIcon="{ex:SymbolIconSource Glyph=Setting}"
           MaxHeight="104"
           HorizontalAlignment="Stretch"
           TextMemberPath="Text"
@@ -51,7 +52,7 @@
             PlaceholderText="Select Names"
             MaxHeight="104"
             HorizontalAlignment="Stretch"
-            QueryIcon="Find"
+            QueryIcon="{ex:SymbolIconSource Glyph=Find}"
             TextMemberPath="Text"
             TokenDelimiter=","
             IsItemClickEnabled="True">
@@ -78,7 +79,10 @@
         </ListView>
       </Border>
 
-      <Button x:Name="ClearButton" Content="Clear All Tokens"/>
+      <StackPanel Orientation="Horizontal" Margin="0,10,0,0">
+        <Button x:Name="ClearButton" Content="Clear All Tokens"/>
+        <Button x:Name="ShowSelectedEmails" Content="Show Selected Emails" Margin="10,0,0,0"/>
+      </StackPanel>
     </StackPanel>
   </Grid>
 </Page>
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/ITokenStringContainer.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/ITokenStringContainer.cs
new file mode 100644
index 00000000000..b665fc478cd
--- /dev/null
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/ITokenStringContainer.cs
@@ -0,0 +1,17 @@
+// Licensed to the .NET Foundation under one or more agreements.
+// The .NET Foundation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+namespace Microsoft.Toolkit.Uwp.UI.Controls
+{
+    /// <summary>
+    /// Provides access to unresolved token string values within the tokenizing text box control
+    /// </summary>
+    public interface ITokenStringContainer
+    {
+        /// <summary>
+        /// Gets or sets the string text for this unresolved token
+        /// </summary>
+        string Text { get; set; }
+    }
+}
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/PretokenStringContainer.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/PretokenStringContainer.cs
index 7c0ef3bf970..eacd5a2a772 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/PretokenStringContainer.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/PretokenStringContainer.cs
@@ -6,7 +6,7 @@
 
 namespace Microsoft.Toolkit.Uwp.UI.Controls
 {
-    internal class PretokenStringContainer : DependencyObject
+    internal class PretokenStringContainer : DependencyObject, ITokenStringContainer
     {
         public string Text
         {
@@ -18,13 +18,25 @@ public string Text
         public static readonly DependencyProperty TextProperty =
             DependencyProperty.Register(nameof(Text), typeof(string), typeof(PretokenStringContainer), new PropertyMetadata(string.Empty));
 
-        public PretokenStringContainer()
+        public bool IsLast { get; private set; }
+
+        public PretokenStringContainer(bool isLast = false)
         {
+            IsLast = isLast;
         }
 
         public PretokenStringContainer(string text)
         {
             Text = text;
         }
+
+        /// <summary>
+        /// Override and provide the content of the container on ToString() so the calling app can access the token string
+        /// </summary>
+        /// <returns>The content of the string token</returns>
+        public override string ToString()
+        {
+            return Text;
+        }
     }
 }
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Properties.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Properties.cs
index 48ca960c60b..6a738b4a5a4 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Properties.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Properties.cs
@@ -91,7 +91,7 @@ public partial class TokenizingTextBox : ListViewBase
         /// </summary>
         public static readonly DependencyProperty QueryIconProperty = DependencyProperty.Register(
             nameof(QueryIcon),
-            typeof(IconElement),
+            typeof(IconSource),
             typeof(TokenizingTextBox),
             new PropertyMetadata(null));
 
@@ -232,9 +232,9 @@ public string PlaceholderText
         /// <summary>
         /// Gets or sets the icon to display in the AutoSuggestBox template part.
         /// </summary>
-        public IconElement QueryIcon
+        public IconSource QueryIcon
         {
-            get => (IconElement)GetValue(QueryIconProperty);
+            get => (IconSource)GetValue(QueryIconProperty);
             set => SetValue(QueryIconProperty, value);
         }
 
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Selection.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Selection.cs
index 31c98e025ff..37366371724 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Selection.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.Selection.cs
@@ -69,6 +69,18 @@ private bool MoveFocusAndSelection(MoveDirection direction)
                 if (index != previousIndex)
                 {
                     var newItem = ContainerFromIndex(index) as TokenizingTextBoxItem;
+
+                    // Check for the new item being a text control.
+                    // this must happen before focus is set to avoid seeing the caret
+                    // jump in come cases
+                    if (Items[index] is PretokenStringContainer && !IsShiftPressed)
+                    {
+                        newItem._autoSuggestTextBox.SelectionLength = 0;
+                        newItem._autoSuggestTextBox.SelectionStart = direction == MoveDirection.Next
+                            ? 0
+                            : newItem._autoSuggestTextBox.Text.Length;
+                    }
+
                     newItem.Focus(FocusState.Keyboard);
 
                     // if no control keys are selected then the selection also becomes just this item
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.cs
index d1846d24e5a..014dc85aa89 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.cs
@@ -57,7 +57,7 @@ public TokenizingTextBox()
         {
             // Setup our base state of our collection
             _innerItemsSource = new InterspersedObservableCollection(new ObservableCollection<object>()); // TODO: Test this still will let us bind to ItemsSource in XAML?
-            _currentTextEdit = _lastTextEdit = new PretokenStringContainer();
+            _currentTextEdit = _lastTextEdit = new PretokenStringContainer(true);
             _innerItemsSource.Insert(_innerItemsSource.Count, _currentTextEdit);
             ItemsSource = _innerItemsSource;
             //// TODO: Consolidate with callback below for ItemsSourceProperty changed?
@@ -80,7 +80,7 @@ private void ItemsSource_PropertyChanged(DependencyObject sender, DependencyProp
             if (ItemsSource != null && ItemsSource.GetType() != typeof(InterspersedObservableCollection))
             {
                 _innerItemsSource = new InterspersedObservableCollection(ItemsSource);
-                _currentTextEdit = _lastTextEdit = new PretokenStringContainer();
+                _currentTextEdit = _lastTextEdit = new PretokenStringContainer(true);
                 _innerItemsSource.Insert(_innerItemsSource.Count, _currentTextEdit);
                 ItemsSource = _innerItemsSource;
             }
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.xaml b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.xaml
index d7e822bdc9e..e58a7ee6635 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.xaml
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBox.xaml
@@ -10,6 +10,7 @@
     <!--  Resources for TokenizingTextBox  -->
     <Thickness x:Key="TokenizingTextBoxBorderThickness">2</Thickness>
     <Thickness x:Key="TokenizingTextBoxPadding">4</Thickness>
+    <Thickness x:Key="TokenizingTextBoxPresenterMargin">0,0,6,0</Thickness>
     <x:Double x:Key="TokenizingTextBoxTokenSpacing">2</x:Double>
 
     <controls:TokenizingTextBoxStyleSelector x:Key="TokenizingTextBoxStyleSelector"
@@ -89,6 +90,7 @@
                           ZoomMode="{TemplateBinding ScrollViewer.ZoomMode}">
 
                 <ItemsPresenter Padding="{TemplateBinding Padding}"
+                                Margin="{StaticResource TokenizingTextBoxPresenterMargin}"
                                 Footer="{TemplateBinding Footer}"
                                 FooterTemplate="{TemplateBinding FooterTemplate}"
                                 FooterTransitions="{TemplateBinding FooterTransitions}"
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.cs b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.cs
index dc1bf58c694..827455c37d2 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.cs
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.cs
@@ -9,6 +9,7 @@
 using Windows.UI.Xaml;
 using Windows.UI.Xaml.Controls;
 using Windows.UI.Xaml.Controls.Primitives;
+using Windows.UI.Xaml.Data;
 using Windows.UI.Xaml.Input;
 
 namespace Microsoft.Toolkit.Uwp.UI.Controls
@@ -76,6 +77,9 @@ private void OnApplyTemplateAutoSuggestBox(AutoSuggestBox auto)
                 _autoSuggestBox.PointerCaptureLost -= AutoSuggestBox_PointerExited;
                 _autoSuggestBox.GotFocus -= AutoSuggestBox_GotFocus;
                 _autoSuggestBox.LostFocus -= AutoSuggestBox_LostFocus;
+
+                // Remove any previous QueryIcon
+                _autoSuggestBox.QueryIcon = null;
             }
 
             _autoSuggestBox = auto;
@@ -93,6 +97,23 @@ private void OnApplyTemplateAutoSuggestBox(AutoSuggestBox auto)
                 _autoSuggestBox.PointerCaptureLost += AutoSuggestBox_PointerExited;
                 _autoSuggestBox.GotFocus += AutoSuggestBox_GotFocus;
                 _autoSuggestBox.LostFocus += AutoSuggestBox_LostFocus;
+
+                // Setup a binding to the QueryIcon of the Parent if we're the last box.
+                if (Content is PretokenStringContainer str && str.IsLast)
+                {
+                    var iconBinding = new Binding()
+                    {
+                        Source = Owner,
+                        Path = new PropertyPath(nameof(Owner.QueryIcon)),
+                        RelativeSource = new RelativeSource() { Mode = RelativeSourceMode.TemplatedParent }
+                    };
+
+                    var iconSourceElement = new IconSourceElement();
+
+                    iconSourceElement.SetBinding(IconSourceElement.IconSourceProperty, iconBinding);
+
+                    _autoSuggestBox.QueryIcon = iconSourceElement;
+                }
             }
         }
 
diff --git a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.xaml b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.xaml
index 6941e0472b8..b6ab76f25e3 100644
--- a/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.xaml
+++ b/Microsoft.Toolkit.Uwp.UI.Controls/TokenizingTextBox/TokenizingTextBoxItem.AutoSuggestBox.xaml
@@ -307,9 +307,7 @@
                                     PlaceholderText="{Binding Path=Owner.PlaceholderText, RelativeSource={RelativeSource Mode=TemplatedParent}}"
                                     Text="{Binding Text, Mode=TwoWay}"
                                     TextBoxStyle="{StaticResource TokenizingTextBoxTextBoxStyle}"/>
-                    <!-- TODO: We need to only do this for our last one OR create an instance per item - QueryIcon="{Binding Path=Owner.QueryIcon, RelativeSource={RelativeSource Mode=TemplatedParent}}" -->
-                    
-                    <!-- TODO: Visual State to style autosuggestbox based on focus -->
+                    <!-- TODO: Visual State to style autosuggestbox based on focus? -->
                 </ControlTemplate>
             </Setter.Value>
         </Setter>