diff --git a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PasteFormatTemplateSelector.cs b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PasteFormatTemplateSelector.cs
new file mode 100644
index 0000000000..18f6b86f33
--- /dev/null
+++ b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PasteFormatTemplateSelector.cs
@@ -0,0 +1,29 @@
+// Copyright (c) Microsoft Corporation
+// The Microsoft Corporation licenses this file to you under the MIT license.
+// See the LICENSE file in the project root for more information.
+
+using AdvancedPaste.Models;
+using Microsoft.UI.Xaml;
+using Microsoft.UI.Xaml.Controls;
+using Microsoft.UI.Xaml.Controls.Primitives;
+
+namespace AdvancedPaste.Controls;
+
+public sealed partial class PasteFormatTemplateSelector : DataTemplateSelector
+{
+    public DataTemplate ItemTemplate { get; set; }
+
+    public DataTemplate ItemTemplateDisabled { get; set; }
+
+    protected override DataTemplate SelectTemplateCore(object item, DependencyObject container)
+    {
+        bool isEnabled = item is PasteFormat pasteFormat && pasteFormat.IsEnabled;
+
+        if (container is SelectorItem selector)
+        {
+            selector.IsEnabled = isEnabled;
+        }
+
+        return isEnabled ? ItemTemplate : ItemTemplateDisabled;
+    }
+}
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PromptBox.xaml b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PromptBox.xaml
index 79a29ac872..69f675d4cb 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PromptBox.xaml
+++ b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Controls/PromptBox.xaml
@@ -410,6 +410,7 @@
                                         Spacing="2">
                                         <Button
                                             Padding="4"
+                                            AutomationProperties.LabeledBy="{x:Bind ThumbsUpFeedback}"
                                             Click="ThumbUpDown_Click"
                                             CommandParameter="True"
                                             Content="{ui:FontIcon Glyph=&#xE8E1;,
@@ -417,11 +418,12 @@
                                             Foreground="{ThemeResource TextFillColorSecondaryBrush}"
                                             Style="{StaticResource SubtleButtonStyle}">
                                             <ToolTipService.ToolTip>
-                                                <TextBlock x:Uid="ThumbsUpFeedback" />
+                                                <TextBlock x:Name="ThumbsUpFeedback" x:Uid="ThumbsUpFeedback" />
                                             </ToolTipService.ToolTip>
                                         </Button>
                                         <Button
                                             Padding="4"
+                                            AutomationProperties.LabeledBy="{x:Bind ThumbsDownFeedback}"
                                             Click="ThumbUpDown_Click"
                                             CommandParameter="False"
                                             Content="{ui:FontIcon Glyph=&#xE8E0;,
@@ -429,7 +431,7 @@
                                             Foreground="{ThemeResource TextFillColorSecondaryBrush}"
                                             Style="{StaticResource SubtleButtonStyle}">
                                             <ToolTipService.ToolTip>
-                                                <TextBlock x:Uid="ThumbsDownFeedback" />
+                                                <TextBlock x:Name="ThumbsDownFeedback" x:Uid="ThumbsDownFeedback" />
                                             </ToolTipService.ToolTip>
                                         </Button>
                                     </StackPanel>
@@ -537,6 +539,7 @@
                         HorizontalAlignment="Stretch"
                         VerticalAlignment="Stretch"
                         ui:VisualExtensions.NormalizedCenterPoint="0.5,0.5"
+                        AutomationProperties.HelpText="{x:Bind ViewModel.CustomAIUnavailableErrorText, Mode=OneWay}"
                         Command="{x:Bind GenerateCustomAICommand}"
                         Content="{ui:FontIcon Glyph=&#xE724;,
                                               FontSize=16}"
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml
index b4e99ebaed..a37e53f49e 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml
+++ b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml
@@ -21,6 +21,77 @@
             x:Name="customActionsToMinHeightConverter"
             ValueIfNonZero="40"
             ValueIfZero="0" />
+        <controls:PasteFormatTemplateSelector x:Key="PasteFormatTemplateSelector">
+            <controls:PasteFormatTemplateSelector.ItemTemplate>
+                <DataTemplate x:DataType="local:PasteFormat">
+                    <Grid
+                        Margin="0"
+                        Padding="-9,0,0,0"
+                        HorizontalAlignment="Stretch"
+                        VerticalAlignment="Stretch"
+                        AutomationProperties.AcceleratorKey="{x:Bind ShortcutText, Mode=OneWay}"
+                        AutomationProperties.AutomationControlType="ListItem"
+                        AutomationProperties.FullDescription="{x:Bind ToolTip, Mode=OneWay}"
+                        AutomationProperties.HelpText="{x:Bind Name, Mode=OneWay}"
+                        AutomationProperties.Name="{x:Bind AccessibleName, Mode=OneWay}">
+                        <Grid.ColumnDefinitions>
+                            <ColumnDefinition Width="26" />
+                            <ColumnDefinition Width="*" />
+                            <ColumnDefinition Width="Auto" />
+                        </Grid.ColumnDefinitions>
+                        <ToolTipService.ToolTip>
+                            <TextBlock Text="{x:Bind ToolTip, Mode=OneWay}" />
+                        </ToolTipService.ToolTip>
+                        <FontIcon
+                            Margin="0,0,0,0"
+                            VerticalAlignment="Center"
+                            AutomationProperties.AccessibilityView="Raw"
+                            FontSize="16"
+                            Glyph="{x:Bind IconGlyph, Mode=OneWay}" />
+                        <TextBlock
+                            Grid.Column="1"
+                            VerticalAlignment="Center"
+                            x:Phase="1"
+                            Text="{x:Bind Name, Mode=OneWay}" />
+                        <TextBlock
+                            Grid.Column="2"
+                            Margin="0,0,8,0"
+                            HorizontalAlignment="Right"
+                            VerticalAlignment="Center"
+                            Foreground="{ThemeResource TextFillColorSecondaryBrush}"
+                            Style="{StaticResource CaptionTextBlockStyle}"
+                            Text="{x:Bind ShortcutText, Mode=OneWay}" />
+                    </Grid>
+                </DataTemplate>
+            </controls:PasteFormatTemplateSelector.ItemTemplate>
+            <controls:PasteFormatTemplateSelector.ItemTemplateDisabled>
+                <DataTemplate x:DataType="local:PasteFormat" AutomationProperties.AccessibilityView="Raw">
+                    <Grid
+                        Margin="0"
+                        Padding="-9,0,0,0"
+                        HorizontalAlignment="Stretch"
+                        VerticalAlignment="Stretch"
+                        AutomationProperties.AccessibilityView="Raw"
+                        Opacity="0.5">
+                        <Grid.ColumnDefinitions>
+                            <ColumnDefinition Width="26" />
+                            <ColumnDefinition Width="*" />
+                            <ColumnDefinition Width="Auto" />
+                        </Grid.ColumnDefinitions>
+                        <FontIcon
+                            Margin="0,0,0,0"
+                            VerticalAlignment="Center"
+                            FontSize="16"
+                            Glyph="{x:Bind IconGlyph, Mode=OneWay}" />
+                        <TextBlock
+                            Grid.Column="1"
+                            VerticalAlignment="Center"
+                            x:Phase="1"
+                            Text="{x:Bind Name, Mode=OneWay}" />
+                    </Grid>
+                </DataTemplate>
+            </controls:PasteFormatTemplateSelector.ItemTemplateDisabled>
+        </controls:PasteFormatTemplateSelector>
         <Style
             x:Key="PaddingLessFlyoutPresenterStyle"
             BasedOn="{StaticResource DefaultFlyoutPresenterStyle}"
@@ -29,57 +100,6 @@
                 <Setter Property="Padding" Value="0" />
             </Style.Setters>
         </Style>
-        <Style x:Key="PasteFormatListViewItemStyle" TargetType="ListViewItem">
-            <Setter Property="Padding" Value="0" />
-            <Setter Property="Margin" Value="0" />
-            <Setter Property="HorizontalContentAlignment" Value="Stretch" />
-            <Setter Property="VerticalContentAlignment" Value="Stretch" />
-        </Style>
-        <DataTemplate x:Key="PasteFormatTemplate" x:DataType="local:PasteFormat">
-            <Button
-                Margin="0"
-                Padding="5,0,5,0"
-                HorizontalAlignment="Stretch"
-                VerticalAlignment="Stretch"
-                HorizontalContentAlignment="Stretch"
-                VerticalContentAlignment="Stretch"
-                AllowFocusOnInteraction="False"
-                BorderThickness="0"
-                Click="ListView_Button_Click"
-                IsEnabled="{x:Bind IsEnabled, Mode=OneWay}">
-                <Grid Opacity="{x:Bind Opacity, Mode=OneWay}">
-                    <Grid.ColumnDefinitions>
-                        <ColumnDefinition Width="26" />
-                        <ColumnDefinition Width="*" />
-                        <ColumnDefinition Width="Auto" />
-                    </Grid.ColumnDefinitions>
-
-                    <ToolTipService.ToolTip>
-                        <TextBlock Text="{x:Bind ToolTip, Mode=OneWay}" />
-                    </ToolTipService.ToolTip>
-                    <FontIcon
-                        Margin="0,0,0,0"
-                        VerticalAlignment="Center"
-                        AutomationProperties.AccessibilityView="Raw"
-                        FontSize="16"
-                        Glyph="{x:Bind IconGlyph, Mode=OneWay}" />
-                    <TextBlock
-                        Grid.Column="1"
-                        VerticalAlignment="Center"
-                        x:Phase="1"
-                        Text="{x:Bind Name, Mode=OneWay}" />
-                    <TextBlock
-                        Grid.Column="2"
-                        Margin="0,0,8,0"
-                        HorizontalAlignment="Right"
-                        VerticalAlignment="Center"
-                        Foreground="{ThemeResource TextFillColorSecondaryBrush}"
-                        Style="{StaticResource CaptionTextBlockStyle}"
-                        Text="{x:Bind ShortcutText, Mode=OneWay}"
-                        Visibility="{x:Bind ShortcutText.Length, Mode=OneWay, Converter={StaticResource countToVisibilityConverter}}" />
-                </Grid>
-            </Button>
-        </DataTemplate>
     </Page.Resources>
     <Page.KeyboardAccelerators>
         <KeyboardAccelerator Key="Escape" Invoked="KeyboardAccelerator_Invoked" />
@@ -196,10 +216,10 @@
                 x:Name="PasteOptionsListView"
                 Grid.Row="0"
                 VerticalAlignment="Bottom"
-                IsItemClickEnabled="False"
-                ItemContainerStyle="{StaticResource PasteFormatListViewItemStyle}"
+                IsItemClickEnabled="True"
+                ItemClick="PasteFormat_ItemClick"
                 ItemContainerTransitions="{x:Null}"
-                ItemTemplate="{StaticResource PasteFormatTemplate}"
+                ItemTemplateSelector="{StaticResource PasteFormatTemplateSelector}"
                 ItemsSource="{x:Bind ViewModel.StandardPasteFormats, Mode=OneWay}"
                 ScrollViewer.VerticalScrollBarVisibility="Visible"
                 ScrollViewer.VerticalScrollMode="Auto"
@@ -217,10 +237,10 @@
                 x:Name="CustomActionsListView"
                 Grid.Row="2"
                 VerticalAlignment="Top"
-                IsItemClickEnabled="False"
-                ItemContainerStyle="{StaticResource PasteFormatListViewItemStyle}"
+                IsItemClickEnabled="True"
+                ItemClick="PasteFormat_ItemClick"
                 ItemContainerTransitions="{x:Null}"
-                ItemTemplate="{StaticResource PasteFormatTemplate}"
+                ItemTemplateSelector="{StaticResource PasteFormatTemplateSelector}"
                 ItemsSource="{x:Bind ViewModel.CustomActionPasteFormats, Mode=OneWay}"
                 ScrollViewer.VerticalScrollBarVisibility="Visible"
                 ScrollViewer.VerticalScrollMode="Auto"
@@ -232,7 +252,6 @@
                 Height="1"
                 HorizontalAlignment="Stretch"
                 Fill="{ThemeResource DividerStrokeColorDefaultBrush}" />
-            <!--  x:Uid="ClipboardHistoryButton"  -->
             <Button
                 Grid.Row="4"
                 Height="32"
@@ -241,6 +260,7 @@
                 HorizontalAlignment="Stretch"
                 HorizontalContentAlignment="Stretch"
                 VerticalContentAlignment="Stretch"
+                AutomationProperties.LabeledBy="{x:Bind ClipboardHistoryButton}"
                 IsEnabled="{x:Bind ViewModel.ClipboardHistoryEnabled, Mode=TwoWay}"
                 Style="{StaticResource SubtleButtonStyle}">
                 <Grid
@@ -259,6 +279,7 @@
                         FontSize="16"
                         Glyph="&#xE81C;" />
                     <TextBlock
+                        x:Name="ClipboardHistoryButton"
                         x:Uid="ClipboardHistoryButton"
                         Grid.Column="1"
                         VerticalAlignment="Center" />
@@ -287,6 +308,7 @@
                                     <Grid
                                         Height="40"
                                         HorizontalAlignment="Stretch"
+                                        AutomationProperties.Name="{x:Bind Description, Mode=OneWay}"
                                         ColumnSpacing="8"
                                         ToolTipService.ToolTip="{x:Bind Content}">
                                         <Grid.ColumnDefinitions>
@@ -308,7 +330,8 @@
                                             TextTrimming="CharacterEllipsis"
                                             Visibility="Visible" />
                                         <Button
-                                            x:Name="moreInfo"
+                                            x:Name="ClipboardHistoryItemMoreOptionsButton"
+                                            x:Uid="ClipboardHistoryItemMoreOptionsButton"
                                             Grid.Column="1"
                                             VerticalAlignment="Center"
                                             Foreground="{ThemeResource TextFillColorSecondaryBrush}"
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml.cs b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml.cs
index 23940b16a5..9c4ac5cc71 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml.cs
+++ b/src/modules/AdvancedPaste/AdvancedPaste/AdvancedPasteXAML/Pages/MainPage.xaml.cs
@@ -130,9 +130,9 @@ namespace AdvancedPaste.Pages
             }
         }
 
-        private async void ListView_Button_Click(object sender, RoutedEventArgs e)
+        private async void PasteFormat_ItemClick(object sender, ItemClickEventArgs e)
         {
-            if (sender is Button { DataContext: PasteFormat format })
+            if (e.ClickedItem is PasteFormat format)
             {
                 await ViewModel.ExecutePasteFormatAsync(format, PasteActionSource.ContextMenu);
             }
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/Models/ClipboardItem.cs b/src/modules/AdvancedPaste/AdvancedPaste/Models/ClipboardItem.cs
index 3927949064..1013108bc9 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/Models/ClipboardItem.cs
+++ b/src/modules/AdvancedPaste/AdvancedPaste/Models/ClipboardItem.cs
@@ -2,6 +2,7 @@
 // The Microsoft Corporation licenses this file to you under the MIT license.
 // See the LICENSE file in the project root for more information.
 
+using AdvancedPaste.Helpers;
 using Microsoft.UI.Xaml.Media.Imaging;
 using Windows.ApplicationModel.DataTransfer;
 
@@ -14,4 +15,8 @@ public class ClipboardItem
     public ClipboardHistoryItem Item { get; set; }
 
     public BitmapImage Image { get; set; }
+
+    public string Description => !string.IsNullOrEmpty(Content) ? Content :
+                                 Image is not null ? ResourceLoaderInstance.ResourceLoader.GetString("ClipboardHistoryImage") :
+                                 string.Empty;
 }
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/Models/PasteFormat.cs b/src/modules/AdvancedPaste/AdvancedPaste/Models/PasteFormat.cs
index e9412b69a6..e1df90897e 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/Models/PasteFormat.cs
+++ b/src/modules/AdvancedPaste/AdvancedPaste/Models/PasteFormat.cs
@@ -54,7 +54,7 @@ public sealed class PasteFormat
 
     public bool IsEnabled { get; private init; }
 
-    public double Opacity => IsEnabled ? 1 : 0.5;
+    public string AccessibleName => $"{Name} ({ShortcutText})";
 
     public string ToolTip => string.IsNullOrEmpty(Prompt) ? $"{Name} ({ShortcutText})" : Prompt;
 
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/Strings/en-us/Resources.resw b/src/modules/AdvancedPaste/AdvancedPaste/Strings/en-us/Resources.resw
index bbd63e916d..1c2839d064 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/Strings/en-us/Resources.resw
+++ b/src/modules/AdvancedPaste/AdvancedPaste/Strings/en-us/Resources.resw
@@ -144,6 +144,15 @@
   <data name="ClipboardHistoryButton.Text" xml:space="preserve">
     <value>Clipboard history</value>
   </data>
+  <data name="ClipboardHistoryButton.[using:Microsoft.UI.Xaml.Automation]AutomationProperties.Name" xml:space="preserve">
+    <value>Clipboard history</value>
+  </data>
+  <data name="ClipboardHistoryImage" xml:space="preserve">
+    <value>Image data</value>
+  </data>
+  <data name="ClipboardHistoryItemMoreOptionsButton.[using:Microsoft.UI.Xaml.Automation]AutomationProperties.Name" xml:space="preserve">
+    <value>More options</value>
+  </data>
   <data name="ClipboardHistoryItemDeleteButton.Text" xml:space="preserve">
     <value>Delete</value>
   </data>