diff --git a/src/modules/keyboardmanager/KeyboardManagerEditor/Resources.resx b/src/modules/keyboardmanager/KeyboardManagerEditor/Resources.resx
index a6fe6f2d62a7..49098653f5a5 100644
--- a/src/modules/keyboardmanager/KeyboardManagerEditor/Resources.resx
+++ b/src/modules/keyboardmanager/KeyboardManagerEditor/Resources.resx
@@ -161,7 +161,7 @@
     <value>To send:</value>
   </data>
   <data name="EditShortcuts_TargetHeader" xml:space="preserve">
-    <value>To send:</value>
+    <value>To:</value>
   </data>
   <data name="EditShortcuts_TargetAppHeader" xml:space="preserve">
     <value>Target app:</value>
@@ -297,10 +297,10 @@
     <comment>Key on a keyboard</comment>
   </data>
   <data name="Mapping_Type_DropDown_Text" xml:space="preserve">
-    <value>Text</value>
+    <value>Send Text</value>
   </data>
   <data name="Mapping_Type_DropDown_Key_Shortcut" xml:space="preserve">
-    <value>Key/Shortcut</value>
+    <value>Send Key/Shortcut</value>
     <comment>Key on a keyboard</comment>
   </data>
   <data name="Mapping_Type_DropDown_Run_Program" xml:space="preserve">
diff --git a/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.cpp b/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.cpp
index 1604bab3dde6..4a33a9604471 100644
--- a/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.cpp
+++ b/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.cpp
@@ -169,6 +169,7 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
     runProgramPathInput.Margin(textInputMargin);
 
     runProgramPathInput.AcceptsReturn(false);
+    runProgramPathInput.IsSpellCheckEnabled(false);
     runProgramPathInput.Visibility(Visibility::Collapsed);
     runProgramPathInput.Width(EditorConstants::TableDropDownHeight);
     controlStackPanel.Children().Append(runProgramPathInput);
@@ -179,12 +180,14 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
     runProgramArgsForProgramInput.Margin(textInputMargin);
 
     runProgramArgsForProgramInput.AcceptsReturn(false);
+    runProgramArgsForProgramInput.IsSpellCheckEnabled(false);
     runProgramArgsForProgramInput.Visibility(Visibility::Collapsed);
     runProgramArgsForProgramInput.Width(EditorConstants::TableDropDownHeight);
     controlStackPanel.Children().Append(runProgramArgsForProgramInput);
     runProgramArgsForProgramInput.HorizontalAlignment(HorizontalAlignment::Left);
 
     auto runProgramStartInDirInput = TextBox();
+    runProgramStartInDirInput.IsSpellCheckEnabled(false);
     runProgramStartInDirInput.PlaceholderText(KeyboardManagerEditorStrings::EditShortcutsStartInDirForProgram());
     runProgramStartInDirInput.Margin(textInputMargin);
 
@@ -202,9 +205,9 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
         }
         Shortcut tempShortcut;
         tempShortcut.isRunProgram = true;
-        tempShortcut.runProgramFilePath = runProgramPathInput.Text().c_str();
-        tempShortcut.runProgramArgs = runProgramArgsForProgramInput.Text().c_str();
-        tempShortcut.runProgramStartInDir = runProgramStartInDirInput.Text().c_str();
+        tempShortcut.runProgramFilePath = ShortcutControl::RemoveExtraQuotes(runProgramPathInput.Text().c_str());
+        tempShortcut.runProgramArgs = ShortcutControl::RemoveExtraQuotes(runProgramArgsForProgramInput.Text().c_str());
+        tempShortcut.runProgramStartInDir = ShortcutControl::RemoveExtraQuotes(runProgramStartInDirInput.Text().c_str());
         // Assign instead of setting the value in the buffer since the previous value may not be a Shortcut
         shortcutRemapBuffer[rowIndex].first[1] = tempShortcut;
 
@@ -219,9 +222,9 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
         }
         Shortcut tempShortcut;
         tempShortcut.isRunProgram = true;
-        tempShortcut.runProgramFilePath = runProgramPathInput.Text().c_str();
-        tempShortcut.runProgramArgs = runProgramArgsForProgramInput.Text().c_str();
-        tempShortcut.runProgramStartInDir = runProgramStartInDirInput.Text().c_str();
+        tempShortcut.runProgramFilePath = ShortcutControl::RemoveExtraQuotes(runProgramPathInput.Text().c_str());
+        tempShortcut.runProgramArgs = ShortcutControl::RemoveExtraQuotes(runProgramArgsForProgramInput.Text().c_str());
+        tempShortcut.runProgramStartInDir = ShortcutControl::RemoveExtraQuotes(runProgramStartInDirInput.Text().c_str());
         // Assign instead of setting the value in the buffer since the previous value may not be a Shortcut
         shortcutRemapBuffer[rowIndex].first[1] = tempShortcut;
         //ShortcutControl::RunProgramTextOnChange(rowIndex, shortcutRemapBuffer, runProgramPathInput, runProgramArgsForProgramInput, runProgramStartInDirInput);
@@ -236,16 +239,15 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
 
         Shortcut tempShortcut;
         tempShortcut.isRunProgram = true;
-        tempShortcut.runProgramFilePath = runProgramPathInput.Text().c_str();
-        tempShortcut.runProgramArgs = runProgramArgsForProgramInput.Text().c_str();
-        tempShortcut.runProgramStartInDir = runProgramStartInDirInput.Text().c_str();
+        tempShortcut.runProgramFilePath = ShortcutControl::RemoveExtraQuotes(runProgramPathInput.Text().c_str());
+        tempShortcut.runProgramArgs = ShortcutControl::RemoveExtraQuotes(runProgramArgsForProgramInput.Text().c_str());
+        tempShortcut.runProgramStartInDir = ShortcutControl::RemoveExtraQuotes(runProgramStartInDirInput.Text().c_str());
         // Assign instead of setting the value in the buffer since the previous value may not be a Shortcut
         shortcutRemapBuffer[rowIndex].first[1] = tempShortcut;
 
         //ShortcutControl::RunProgramTextOnChange(rowIndex, shortcutRemapBuffer, runProgramPathInput, runProgramArgsForProgramInput, runProgramStartInDirInput);
     });
 
-
     // add grid for when it's a key/shortcut
     auto shortcutGrid = keyboardRemapControlObjects.back()[1]->shortcutDropDownVariableSizedWrapGrid.as<VariableSizedWrapGrid>();
     auto gridMargin = Windows::UI::Xaml::Thickness();
@@ -530,15 +532,14 @@ void ShortcutControl::AddNewShortcutControlRow(StackPanel& parent, std::vector<s
     }
 }
 
-void ShortcutControl::RunProgramTextOnChange(const int rowIndex, RemapBuffer shortcutRemapBuffer, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramPathInput, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramArgsForProgramInput, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramStartInDirInput)
+std::wstring ShortcutControl::RemoveExtraQuotes(const std::wstring& str)
 {
-    Shortcut tempShortcut;
-    tempShortcut.isRunProgram = true;
-    tempShortcut.runProgramFilePath = runProgramPathInput.Text().c_str();
-    tempShortcut.runProgramArgs = runProgramArgsForProgramInput.Text().c_str();
-    tempShortcut.runProgramStartInDir = runProgramStartInDirInput.Text().c_str();
-    // Assign instead of setting the value in the buffer since the previous value may not be a Shortcut
-    shortcutRemapBuffer[rowIndex].first[1] = tempShortcut;
+    if (!str.empty() && str.front() == L'"' && str.back() == L'"')
+    {
+        return str.substr(1, str.size() - 2);
+    }
+
+    return str;
 }
 
 ShortcutControl::ShortcutType ShortcutControl::GetShortcutType(const winrt::Windows::UI::Xaml::Controls::ComboBox& typeCombo)
diff --git a/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.h b/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.h
index ae9d6b3f5a78..8fc98fb390db 100644
--- a/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.h
+++ b/src/modules/keyboardmanager/KeyboardManagerEditorLibrary/ShortcutControl.h
@@ -71,7 +71,7 @@ class ShortcutControl
 
     static ShortcutType GetShortcutType(const winrt::Windows::UI::Xaml::Controls::ComboBox& typeCombo);
 
-    static void ShortcutControl::RunProgramTextOnChange(const int rowIndex, RemapBuffer shortcutRemapBuffer, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramPathInput, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramArgsForProgramInput, const winrt::Windows::UI::Xaml::Controls::TextBox& runProgramStartInDirInput);
+    static std::wstring ShortcutControl::RemoveExtraQuotes(const std::wstring& str);    
 
     // Function to return the stack panel element of the ShortcutControl. This is the externally visible UI element which can be used to add it to other layouts
     StackPanel GetShortcutControl();
diff --git a/src/settings-ui/Settings.UI.Library/KeysDataModel.cs b/src/settings-ui/Settings.UI.Library/KeysDataModel.cs
index 608169a94919..32a2713e1d6f 100644
--- a/src/settings-ui/Settings.UI.Library/KeysDataModel.cs
+++ b/src/settings-ui/Settings.UI.Library/KeysDataModel.cs
@@ -3,6 +3,7 @@
 // See the LICENSE file in the project root for more information.
 
 using System.Collections.Generic;
+using System.IO;
 using System.Linq;
 using System.Text.Json;
 using System.Text.Json.Serialization;
@@ -24,8 +25,19 @@ public class KeysDataModel
         [JsonPropertyName("runProgramFilePath")]
         public string RunProgramFilePath { get; set; }
 
+        [JsonPropertyName("runProgramArgs")]
+        public string RunProgramArgs { get; set; }
+
+        [JsonPropertyName("isRunProgram")]
+        public bool IsRunProgram { get; set; }
+
         private static List<string> MapKeys(string stringOfKeys)
         {
+            if (stringOfKeys == null)
+            {
+                return new List<string>();
+            }
+
             return stringOfKeys
                 .Split(';')
                 .Select(uint.Parse)
@@ -40,9 +52,49 @@ public List<string> GetMappedOriginalKeys()
 
         public List<string> GetMappedNewRemapKeys()
         {
+            if (IsRunProgram)
+            {
+                // we're going to just pretend this is a "key" if we have a RunProgramFilePath
+                if (string.IsNullOrEmpty(RunProgramFilePath))
+                {
+                    return new List<string>();
+                }
+                else
+                {
+                    return new List<string> { FormatFakeKeyForDisplay() };
+                }
+            }
+
             return string.IsNullOrEmpty(NewRemapString) ? MapKeys(NewRemapKeys) : new List<string> { NewRemapString };
         }
 
+        private string FormatFakeKeyForDisplay()
+        {
+            // was going to use this:
+            // var fakeKey = Path.GetFileName(RunProgramFilePath);
+            // but I like this better:
+            var fakeKey = RunProgramFilePath;
+
+            if (fakeKey.Length > 15)
+            {
+                fakeKey = $"...{fakeKey.Substring(fakeKey.Length - 12)}";
+            }
+
+            if (!string.IsNullOrEmpty(RunProgramArgs))
+            {
+                if (RunProgramArgs.Length > 10)
+                {
+                    fakeKey = $"{fakeKey} {RunProgramArgs.Substring(0, 7)}...";
+                }
+                else
+                {
+                    fakeKey = $"{fakeKey} {RunProgramArgs}";
+                }
+            }
+
+            return fakeKey;
+        }
+
         public string ToJsonString()
         {
             return JsonSerializer.Serialize(this);
diff --git a/src/settings-ui/Settings.UI/SettingsXAML/Views/DashboardPage.xaml b/src/settings-ui/Settings.UI/SettingsXAML/Views/DashboardPage.xaml
index 6e9c34d61399..4e92e4a2ec70 100644
--- a/src/settings-ui/Settings.UI/SettingsXAML/Views/DashboardPage.xaml
+++ b/src/settings-ui/Settings.UI/SettingsXAML/Views/DashboardPage.xaml
@@ -216,11 +216,19 @@
                                                     </ItemsControl.ItemTemplate>
                                                 </ItemsControl>
                                             </Border>
+                                            
                                             <custom:IsEnabledTextBlock
                                                 x:Uid="To"
                                                 Margin="8,0,8,0"
                                                 VerticalAlignment="Center"
+                                                Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay, Converter={StaticResource BoolToInvertedVisibilityConverter}}"
                                                 Style="{StaticResource SecondaryIsEnabledTextBlockStyle}" />
+                                            <custom:IsEnabledTextBlock
+                                                 x:Uid="Starts"
+                                                 Margin="8,0,8,0"
+                                                 VerticalAlignment="Center"
+                                                 Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay}"
+                                                 Style="{StaticResource SecondaryIsEnabledTextBlockStyle}" />
                                             <Border
                                                 Padding="8,4"
                                                 Background="{ThemeResource CardBackgroundFillColorDefaultBrush}"
@@ -252,6 +260,7 @@
                                             <TextBlock
                                                 Margin="4,0,0,0"
                                                 VerticalAlignment="Center"
+                                                Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay, Converter={StaticResource BoolToInvertedVisibilityConverter}}"
                                                 Foreground="{ThemeResource AccentFillColorDefaultBrush}"
                                                 Text="{x:Bind TargetApp}" />
                                         </StackPanel>
diff --git a/src/settings-ui/Settings.UI/SettingsXAML/Views/KeyboardManagerPage.xaml b/src/settings-ui/Settings.UI/SettingsXAML/Views/KeyboardManagerPage.xaml
index f4ef3b5ece3e..0def811ae2d1 100644
--- a/src/settings-ui/Settings.UI/SettingsXAML/Views/KeyboardManagerPage.xaml
+++ b/src/settings-ui/Settings.UI/SettingsXAML/Views/KeyboardManagerPage.xaml
@@ -14,6 +14,10 @@
 
     <Page.Resources>
         <converters:CollectionVisibilityConverter x:Key="CollectionVisibilityConverter" />
+        <converters:BoolToVisibilityConverter
+            x:Key="BoolToInvertedVisibilityConverter"
+            FalseValue="Visible"
+            TrueValue="Collapsed" />
         <Style x:Name="KeysListViewContainerStyle" TargetType="ListViewItem">
             <Setter Property="IsTabStop" Value="False" />
         </Style>
@@ -150,12 +154,22 @@
                                                 </ItemsPanelTemplate>
                                             </ItemsControl.ItemsPanel>
                                         </ItemsControl>
+                                        
                                         <custom:IsEnabledTextBlock
                                             x:Uid="To"
                                             Margin="8,0,8,0"
                                             VerticalAlignment="Center"
+                                            Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay, Converter={StaticResource BoolToInvertedVisibilityConverter}}"
                                             Style="{StaticResource SecondaryIsEnabledTextBlockStyle}" />
 
+                                        <custom:IsEnabledTextBlock
+                                            x:Uid="Starts"
+                                            Margin="8,0,8,0"
+                                            VerticalAlignment="Center"
+                                            Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay}"
+                                            Style="{StaticResource SecondaryIsEnabledTextBlockStyle}" />
+
+
                                         <ItemsControl
                                             Name="KeyboardManager_RemappedTo"
                                             x:Uid="KeyboardManager_RemappedTo"
@@ -172,7 +186,8 @@
                                             Margin="16,0,0,0"
                                             Padding="12,4,12,6"
                                             VerticalAlignment="Center"
-                                            CornerRadius="12">
+                                            CornerRadius="12"
+                                            Visibility="{x:Bind Path=IsRunProgram, Mode=OneWay, Converter={StaticResource BoolToInvertedVisibilityConverter}}">
                                             <Border.Background>
                                                 <SolidColorBrush Opacity="0.3" Color="{ThemeResource SystemAccentColor}" />
                                             </Border.Background>
diff --git a/src/settings-ui/Settings.UI/Strings/en-us/Resources.resw b/src/settings-ui/Settings.UI/Strings/en-us/Resources.resw
index a1a1f7fc6955..df2273196467 100644
--- a/src/settings-ui/Settings.UI/Strings/en-us/Resources.resw
+++ b/src/settings-ui/Settings.UI/Strings/en-us/Resources.resw
@@ -2354,7 +2354,11 @@ From there, simply click on one of the supported files in the File Explorer and
     <value>to</value>
     <comment>as in: from x to y</comment>
   </data>
-  <data name="LearnMore_Awake.Text" xml:space="preserve">
+  <data name="Starts.Text" xml:space="preserve">
+    <value>starts</value>
+    <comment>as in: doing x start y</comment>
+  </data>
+	<data name="LearnMore_Awake.Text" xml:space="preserve">
     <value>Learn more about Awake</value>
     <comment>Awake is a product name, do not loc</comment>
   </data>
diff --git a/src/settings-ui/Settings.UI/ViewModels/KeyboardManagerViewModel.cs b/src/settings-ui/Settings.UI/ViewModels/KeyboardManagerViewModel.cs
index a67a7ec668e0..d59f406b4a4a 100644
--- a/src/settings-ui/Settings.UI/ViewModels/KeyboardManagerViewModel.cs
+++ b/src/settings-ui/Settings.UI/ViewModels/KeyboardManagerViewModel.cs
@@ -194,7 +194,7 @@ public static List<AppSpecificKeysDataModel> CombineShortcutLists(List<KeysDataM
             }
             else
             {
-                return globalShortcutList.ConvertAll(x => new AppSpecificKeysDataModel { OriginalKeys = x.OriginalKeys, NewRemapKeys = x.NewRemapKeys, NewRemapString = x.NewRemapString, TargetApp = allAppsDescription }).Concat(appSpecificShortcutList).ToList();
+                return globalShortcutList.ConvertAll(x => new AppSpecificKeysDataModel { OriginalKeys = x.OriginalKeys, NewRemapKeys = x.NewRemapKeys, NewRemapString = x.NewRemapString, RunProgramFilePath = x.RunProgramFilePath, IsRunProgram = x.IsRunProgram, RunProgramArgs = x.RunProgramArgs, TargetApp = allAppsDescription }).Concat(appSpecificShortcutList).ToList();
             }
         }