diff --git a/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-100.png b/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-100.png
deleted file mode 100644
index 6d57b166f2..0000000000
Binary files a/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-100.png and /dev/null differ
diff --git a/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-200.png b/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-200.png
deleted file mode 100644
index ebba22951f..0000000000
Binary files a/src/cascadia/CascadiaPackage/ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.scale-200.png and /dev/null differ
diff --git a/src/cascadia/TerminalSettingsEditor/Extensions.cpp b/src/cascadia/TerminalSettingsEditor/Extensions.cpp
index ffaff9a33d..a3aec0ad7c 100644
--- a/src/cascadia/TerminalSettingsEditor/Extensions.cpp
+++ b/src/cascadia/TerminalSettingsEditor/Extensions.cpp
@@ -500,6 +500,12 @@ namespace winrt::Microsoft::Terminal::Settings::Editor::implementation
         {
             if (!extPkgVM.Package().DisplayName().empty())
             {
+                // Check if the first char of the icon is in the Segoe MDL2 Icons list
+                const auto ch = til::at(extPkgVM.Package().Icon(), 0);
+                if (ch >= L'\uE700' && ch <= L'\uF8FF')
+                {
+                    return ComplexTemplateWithFontIcon();
+                }
                 return ComplexTemplate();
             }
             return DefaultTemplate();
diff --git a/src/cascadia/TerminalSettingsEditor/Extensions.h b/src/cascadia/TerminalSettingsEditor/Extensions.h
index 6b7eafad57..a9379829d2 100644
--- a/src/cascadia/TerminalSettingsEditor/Extensions.h
+++ b/src/cascadia/TerminalSettingsEditor/Extensions.h
@@ -183,6 +183,7 @@ namespace winrt::Microsoft::Terminal::Settings::Editor::implementation
 
         WINRT_PROPERTY(Windows::UI::Xaml::DataTemplate, DefaultTemplate, nullptr);
         WINRT_PROPERTY(Windows::UI::Xaml::DataTemplate, ComplexTemplate, nullptr);
+        WINRT_PROPERTY(Windows::UI::Xaml::DataTemplate, ComplexTemplateWithFontIcon, nullptr);
     };
 };
 
diff --git a/src/cascadia/TerminalSettingsEditor/Extensions.idl b/src/cascadia/TerminalSettingsEditor/Extensions.idl
index 4dc3018c36..6093471014 100644
--- a/src/cascadia/TerminalSettingsEditor/Extensions.idl
+++ b/src/cascadia/TerminalSettingsEditor/Extensions.idl
@@ -77,5 +77,6 @@ namespace Microsoft.Terminal.Settings.Editor
 
         Windows.UI.Xaml.DataTemplate DefaultTemplate;
         Windows.UI.Xaml.DataTemplate ComplexTemplate;
+        Windows.UI.Xaml.DataTemplate ComplexTemplateWithFontIcon;
     }
 }
diff --git a/src/cascadia/TerminalSettingsEditor/Extensions.xaml b/src/cascadia/TerminalSettingsEditor/Extensions.xaml
index eec3e69290..a3f80cb2e7 100644
--- a/src/cascadia/TerminalSettingsEditor/Extensions.xaml
+++ b/src/cascadia/TerminalSettingsEditor/Extensions.xaml
@@ -42,6 +42,7 @@
 
             <local:ExtensionPackageTemplateSelector x:Key="ExtensionPackageIdentifierTemplateSelector"
                                                     ComplexTemplate="{StaticResource ComplexExtensionIdentifierTemplate}"
+                                                    ComplexTemplateWithFontIcon="{StaticResource ComplexExtensionIdentifierTemplateWithFontIcon}"
                                                     DefaultTemplate="{StaticResource DefaultExtensionIdentifierTemplate}" />
 
             <DataTemplate x:Key="DefaultExtensionIdentifierTemplate"
@@ -91,8 +92,37 @@
                 </Grid>
             </DataTemplate>
 
+            <DataTemplate x:Key="ComplexExtensionIdentifierTemplateWithFontIcon"
+                          x:DataType="local:ExtensionPackageViewModel">
+                <Grid>
+                    <Grid.ColumnDefinitions>
+                        <ColumnDefinition Width="Auto" />
+                        <ColumnDefinition Width="*" />
+                    </Grid.ColumnDefinitions>
+                    <Grid.RowDefinitions>
+                        <RowDefinition Height="Auto" />
+                        <RowDefinition Height="Auto" />
+                    </Grid.RowDefinitions>
+
+                    <FontIcon Grid.Row="0"
+                              Grid.RowSpan="2"
+                              Grid.Column="0"
+                              Margin="0,0,8,0"
+                              FontSize="32"
+                              Glyph="{x:Bind Package.Icon}" />
+                    <TextBlock Grid.Row="0"
+                               Grid.Column="1"
+                               Text="{x:Bind Package.DisplayName}" />
+                    <TextBlock Grid.Row="1"
+                               Grid.Column="1"
+                               Style="{StaticResource SettingsPageItemDescriptionStyle}"
+                               Text="{x:Bind Package.Source}" />
+                </Grid>
+            </DataTemplate>
+
             <local:ExtensionPackageTemplateSelector x:Key="ExtensionPackageNavigatorTemplateSelector"
                                                     ComplexTemplate="{StaticResource ComplexExtensionNavigatorTemplate}"
+                                                    ComplexTemplateWithFontIcon="{StaticResource ComplexExtensionNavigatorTemplateWithFontIcon}"
                                                     DefaultTemplate="{StaticResource DefaultExtensionNavigatorTemplate}" />
 
             <DataTemplate x:Key="DefaultExtensionNavigatorTemplate"
@@ -146,6 +176,31 @@
                 </Button>
             </DataTemplate>
 
+            <DataTemplate x:Key="ComplexExtensionNavigatorTemplateWithFontIcon"
+                          x:DataType="local:ExtensionPackageViewModel">
+                <Button AutomationProperties.Name="{x:Bind AccessibleName}"
+                        Click="ExtensionNavigator_Click"
+                        Style="{StaticResource NavigatorButtonStyle}"
+                        Tag="{x:Bind}">
+                    <Grid>
+                        <Grid.ColumnDefinitions>
+                            <ColumnDefinition Width="*" />
+                            <ColumnDefinition Width="Auto" />
+                        </Grid.ColumnDefinitions>
+
+                        <ContentPresenter Content="{x:Bind}"
+                                          ContentTemplate="{StaticResource ComplexExtensionIdentifierTemplateWithFontIcon}" />
+
+                        <ToggleSwitch Grid.Column="1"
+                                      HorizontalAlignment="Right"
+                                      VerticalAlignment="Center"
+                                      AutomationProperties.Name="{x:Bind AccessibleName}"
+                                      IsOn="{x:Bind Enabled, Mode=TwoWay}"
+                                      Style="{StaticResource ToggleSwitchInExpanderStyle}" />
+                    </Grid>
+                </Button>
+            </DataTemplate>
+
             <DataTemplate x:Key="FragmentProfileViewModelTemplate"
                           x:DataType="local:FragmentProfileViewModel">
                 <muxc:Expander AutomationProperties.Name="{x:Bind AccessibleName}"
diff --git a/src/cascadia/TerminalSettingsModel/SshHostGenerator.cpp b/src/cascadia/TerminalSettingsModel/SshHostGenerator.cpp
index 45711c711e..e3c7ebbcb3 100644
--- a/src/cascadia/TerminalSettingsModel/SshHostGenerator.cpp
+++ b/src/cascadia/TerminalSettingsModel/SshHostGenerator.cpp
@@ -12,8 +12,8 @@
 static constexpr std::wstring_view SshHostGeneratorNamespace{ L"Windows.Terminal.SSH" };
 
 static constexpr std::wstring_view PROFILE_TITLE_PREFIX = L"SSH - ";
-static constexpr std::wstring_view PROFILE_ICON_PATH = L"ms-appx:///ProfileIcons/{550ce7b8-d500-50ad-8a1a-c400c3262db3}.png";
-static constexpr std::wstring_view GENERATOR_ICON_PATH = L"ms-appx:///ProfileGeneratorIcons/SSH.png";
+static constexpr std::wstring_view PROFILE_ICON_PATH = L"\uE977"; // PC1
+static constexpr std::wstring_view GENERATOR_ICON_PATH = L"\uE969"; // StorageNetworkWireless
 
 // OpenSSH is installed under System32 when installed via Optional Features
 static constexpr std::wstring_view SSH_EXE_PATH1 = L"%SystemRoot%\\System32\\OpenSSH\\ssh.exe";
diff --git a/src/features.xml b/src/features.xml
index 569acb9d6e..894875ecd5 100644
--- a/src/features.xml
+++ b/src/features.xml
@@ -100,6 +100,11 @@
         <description>Enables the dynamic profile generator for OpenSSH config files</description>
         <id>9031</id>
         <stage>AlwaysDisabled</stage>
+        <alwaysEnabledBrandingTokens>
+            <brandingToken>Dev</brandingToken>
+            <brandingToken>Canary</brandingToken>
+            <brandingToken>Preview</brandingToken>
+        </alwaysEnabledBrandingTokens>
     </feature>
 
     <feature>