diff --git a/Source/Libraries/GSF.TimeSeries/UI/Converters/MenuItemIconConverter.cs b/Source/Libraries/GSF.TimeSeries/UI/Converters/MenuItemIconConverter.cs
new file mode 100644
index 00000000000..6590d23b5a6
--- /dev/null
+++ b/Source/Libraries/GSF.TimeSeries/UI/Converters/MenuItemIconConverter.cs
@@ -0,0 +1,213 @@
+//******************************************************************************************************
+//  MenuItemIconConverter.cs - Gbtc
+//
+//  Copyright © 2026, Grid Protection Alliance.  All Rights Reserved.
+//
+//  Licensed to the Grid Protection Alliance (GPA) under one or more contributor license agreements. See
+//  the NOTICE file distributed with this work for additional information regarding copyright ownership.
+//  The GPA licenses this file to you under the MIT License (MIT), the "License"; you may
+//  not use this file except in compliance with the License. You may obtain a copy of the License at:
+//
+//      http://www.opensource.org/licenses/MIT
+//
+//  Unless agreed to in writing, the subject software distributed under the License is distributed on an
+//  "AS-IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. Refer to the
+//  License for the specific language governing permissions and limitations.
+//
+//  Code Modification History:
+//  ----------------------------------------------------------------------------------------------------
+//  06/19/2026 - J. Ritchie Carroll
+//       Generated original version of source code.
+//
+//******************************************************************************************************
+
+using System;
+using System.Globalization;
+using System.IO;
+using System.Windows;
+using System.Windows.Controls;
+using System.Windows.Data;
+using System.Windows.Interop;
+using System.Windows.Media;
+using System.Windows.Media.Imaging;
+using GSF.IO;
+using DrawingIcon = System.Drawing.Icon;
+
+namespace GSF.TimeSeries.UI.Converters
+{
+    /// <summary>
+    /// Represents an <see cref="IMultiValueConverter"/> that produces the image to display in the icon
+    /// region of a menu item from an icon reference and/or an external process path.
+    /// </summary>
+    /// <remarks>
+    /// The converter expects two bound values: the first is the explicit icon reference (i.e., the menu item's
+    /// <c>Icon</c> value) and the second is the external process path (i.e., the menu item's
+    /// <c>ExternalProcessPath</c> value). When the icon reference is defined, the referenced image is loaded and
+    /// displayed. When no icon is defined but an external process path is set, the embedded application icon for
+    /// the external process is extracted and used instead. The converter returns a new <see cref="Image"/> instance
+    /// on each evaluation so that the result can be safely assigned to the <see cref="MenuItem.Icon"/> property from
+    /// within a shared <see cref="Style"/> setter (a single <see cref="FrameworkElement"/> instance cannot be the
+    /// logical child of multiple menu items).
+    /// </remarks>
+    public class MenuItemIconConverter : IMultiValueConverter
+    {
+        /// <summary>
+        /// Default width and height, in device-independent pixels, of a generated menu item icon.
+        /// </summary>
+        public const double DefaultIconSize = 16.0D;
+
+        /// <summary>
+        /// Returns an <see cref="Image"/> element representing the icon for a menu item.
+        /// </summary>
+        /// <param name="values">
+        /// The bound values: <c>values[0]</c> is the explicit icon reference and <c>values[1]</c> is the external
+        /// process path.
+        /// </param>
+        /// <param name="targetType">The type of the binding target property.</param>
+        /// <param name="parameter">Optional icon size override; when parsable as a <see cref="double"/>, overrides <see cref="DefaultIconSize"/>.</param>
+        /// <param name="culture">The culture to use in the converter.</param>
+        /// <returns>An <see cref="Image"/> when an icon could be resolved; otherwise, <c>null</c>.</returns>
+        public object Convert(object[] values, Type targetType, object parameter, CultureInfo culture)
+        {
+            if ((object)values == null)
+                return null;
+
+            string icon = values.Length > 0 ? values[0] as string : null;
+            string externalProcessPath = values.Length > 1 ? values[1] as string : null;
+
+            ImageSource source = null;
+
+            // (1) Use the explicitly defined icon when one is specified.
+            if (!string.IsNullOrWhiteSpace(icon))
+                source = LoadImageSource(icon);
+
+            // (2) Otherwise, fall back to the embedded icon of the external process, when defined.
+            if ((object)source == null && !string.IsNullOrWhiteSpace(externalProcessPath))
+                source = ExtractAssociatedIcon(externalProcessPath);
+
+            if ((object)source == null)
+                return null;
+
+            double size = DefaultIconSize;
+
+            if (parameter != null && double.TryParse(parameter.ToString(), NumberStyles.Any, CultureInfo.InvariantCulture, out double parsedSize) && parsedSize > 0.0D)
+                size = parsedSize;
+
+            return new Image
+            {
+                Source = source,
+                Width = size,
+                Height = size,
+                Stretch = Stretch.Uniform,
+                SnapsToDevicePixels = true
+            };
+        }
+
+        /// <summary>
+        /// Not supported; this converter only supports one-way conversion.
+        /// </summary>
+        public object[] ConvertBack(object value, Type[] targetTypes, object parameter, CultureInfo culture)
+        {
+            throw new NotSupportedException();
+        }
+
+        /// <summary>
+        /// Loads an <see cref="ImageSource"/> from an icon reference that may be a WPF pack/resource URI or a file path.
+        /// </summary>
+        /// <remarks>
+        /// Example to load an embedded image from the GSF.TimeSeries.UI assembly:
+        /// <code>
+        /// &lt;MenuDataItem Icon="/GSF.TimeSeries.UI;component/images/Configure.png" MenuText="Measurements" ... /&gt;
+        /// </code>
+        /// </remarks>
+        private static ImageSource LoadImageSource(string icon)
+        {
+            try
+            {
+                icon = Environment.ExpandEnvironmentVariables(icon.Trim());
+
+                Uri uri;
+
+                if (icon.StartsWith("pack://", StringComparison.OrdinalIgnoreCase))
+                {
+                    // Absolute pack URI, e.g.: pack://application:,,,/GSF.TimeSeries.UI;component/images/Icon.png
+                    uri = new Uri(icon, UriKind.Absolute);
+                }
+                else if (icon.StartsWith("/", StringComparison.Ordinal))
+                {
+                    // Relative pack URI, e.g.: /GSF.TimeSeries.UI;component/images/Icon.png - resolved against the application.
+                    uri = new Uri(icon, UriKind.Relative);
+                }
+                else if (Uri.TryCreate(icon, UriKind.Absolute, out Uri absoluteUri) && !absoluteUri.IsFile)
+                {
+                    // Any other absolute URI (e.g. http://) is used as-is.
+                    uri = absoluteUri;
+                }
+                else
+                {
+                    // Treat as a file path, resolving relative paths against the application directory.
+                    string path = FilePath.GetAbsolutePath(icon);
+
+                    if (!File.Exists(path))
+                        return null;
+
+                    uri = new Uri(path, UriKind.Absolute);
+                }
+
+                BitmapImage bitmap = new BitmapImage();
+
+                bitmap.BeginInit();
+                bitmap.CacheOption = BitmapCacheOption.OnLoad;
+                bitmap.UriSource = uri;
+                bitmap.EndInit();
+                bitmap.Freeze();
+
+                return bitmap;
+            }
+            catch
+            {
+                // Icon is best-effort: a bad reference simply yields no icon rather than failing the menu render.
+                return null;
+            }
+        }
+
+        /// <summary>
+        /// Extracts the embedded application icon associated with an external process executable.
+        /// </summary>
+        private static ImageSource ExtractAssociatedIcon(string processPath)
+        {
+            try
+            {
+                processPath = Environment.ExpandEnvironmentVariables(processPath.Trim());
+
+                // System.Drawing.Icon.ExtractAssociatedIcon requires an existing local file path.
+                if (!File.Exists(processPath))
+                {
+                    string resolvedPath = FilePath.GetAbsolutePath(processPath);
+
+                    if (!File.Exists(resolvedPath))
+                        return null;
+
+                    processPath = resolvedPath;
+                }
+
+                using (DrawingIcon icon = DrawingIcon.ExtractAssociatedIcon(processPath))
+                {
+                    if ((object)icon == null)
+                        return null;
+
+                    // CreateBitmapSourceFromHIcon copies the icon data, so the source GDI icon can be disposed afterward.
+                    ImageSource source = Imaging.CreateBitmapSourceFromHIcon(icon.Handle, Int32Rect.Empty, BitmapSizeOptions.FromEmptyOptions());
+                    source.Freeze();
+
+                    return source;
+                }
+            }
+            catch
+            {
+                // Icon extraction is best-effort: failures simply yield no icon.
+                return null;
+            }
+        }
+    }
+}
diff --git a/Source/Libraries/GSF.TimeSeries/UI/GSF.TimeSeries.UI.csproj b/Source/Libraries/GSF.TimeSeries/UI/GSF.TimeSeries.UI.csproj
index b74922a77a8..eb4864f5c57 100755
--- a/Source/Libraries/GSF.TimeSeries/UI/GSF.TimeSeries.UI.csproj
+++ b/Source/Libraries/GSF.TimeSeries/UI/GSF.TimeSeries.UI.csproj
@@ -48,6 +48,7 @@
     <Reference Include="System.Data.DataSetExtensions" />
     <Reference Include="Microsoft.CSharp" />
     <Reference Include="System.Data" />
+    <Reference Include="System.Drawing" />
     <Reference Include="System.Xml" />
     <Reference Include="WindowsBase" />
   </ItemGroup>
@@ -61,6 +62,7 @@
     <Compile Include="Binding\GridButtonCommand.cs" />
     <Compile Include="CommonFunctions.cs" />
     <Compile Include="Converters\IndexToBooleanConverter.cs" />
+    <Compile Include="Converters\MenuItemIconConverter.cs" />
     <Compile Include="Converters\DictionaryToKeyValuePairConverter.cs" />
     <Compile Include="Converters\NotConverter.cs" />
     <Compile Include="Converters\ObjectToVisibilityConverter.cs" />
diff --git a/Source/Libraries/GSF.TimeSeries/UI/WPF/Commands/MenuCommand.cs b/Source/Libraries/GSF.TimeSeries/UI/WPF/Commands/MenuCommand.cs
index 4f58462cb98..0abc5afa4ef 100755
--- a/Source/Libraries/GSF.TimeSeries/UI/WPF/Commands/MenuCommand.cs
+++ b/Source/Libraries/GSF.TimeSeries/UI/WPF/Commands/MenuCommand.cs
@@ -29,6 +29,7 @@
 using System.Diagnostics;
 using System.Linq;
 using System.Reflection;
+using System.Windows;
 using System.Windows.Input;
 using GSF.IO;
 using GSF.Security;
@@ -185,26 +186,37 @@ public void Execute(object parameter)
             bool hasUserControlPath = !string.IsNullOrEmpty(UserControlPath);
             bool hasExternalProcessPath = !string.IsNullOrEmpty(ExternalProcessPath);
 
-            if (hasUserControlAssembly != hasUserControlPath)
-                throw new InvalidOperationException("UserControlAssembly and UserControlPath must both be populated or neither");
+            if (!hasExternalProcessPath && hasUserControlAssembly != hasUserControlPath)
+                throw new InvalidOperationException("UserControlAssembly and UserControlPath must both be populated or neither when ExternalProcessPath is not set");
 
             if (hasUserControlAssembly == hasExternalProcessPath)
                 throw new InvalidOperationException("One of UserControlAssembly and ExternalProcessPath must be populated, but not both");
 
-            try
+            if (hasExternalProcessPath)
             {
-                if (hasExternalProcessPath)
+                try
+                {
+                    // If ExternalProcessPath requires arguments, they can be specified in the UserControlPath property
+                    Process.Start(ExternalProcessPath, UserControlPath)?.Dispose();
+                }
+                catch (Exception ex)
                 {
-                    Process.Start(ExternalProcessPath).Dispose();
-                    return;
+                    CommonFunctions.Popup($"Failed to launch external process \"{ExternalProcessPath}\": {ex.Message}", "Menu Launch Exception:", MessageBoxImage.Error);
+                    CommonFunctions.LogException(null, "Menu Launch Exception", ex);
                 }
+                return;
+            }
 
-                Assembly assembly = Assembly.LoadFrom(FilePath.GetAbsolutePath(m_userControlAssembly));
-                CommonFunctions.LoadUserControl(m_description, assembly.GetType(m_userControlPath));
+            try
+            {
+                Assembly assembly = Assembly.LoadFrom(FilePath.GetAbsolutePath(UserControlAssembly));
+                CommonFunctions.LoadUserControl(m_description, assembly.GetType(UserControlPath));
             }
             catch (Exception ex)
             {
-                throw new InvalidOperationException(string.Format("Failed to create user control {0}: {1}", m_userControlPath, ex.Message), ex);
+                CommonFunctions.Popup($"Failed to create user control {UserControlAssembly}: {ex.Message}", "Menu Load Exception:", MessageBoxImage.Error);
+                CommonFunctions.LogException(null, "Menu Load Exception", ex);
+
             }
         }
 
diff --git a/Source/Libraries/GSF.TimeSeries/UI/WPF/Resources/StyleResource.xaml b/Source/Libraries/GSF.TimeSeries/UI/WPF/Resources/StyleResource.xaml
index aa86b2f0290..ebb556324e4 100644
--- a/Source/Libraries/GSF.TimeSeries/UI/WPF/Resources/StyleResource.xaml
+++ b/Source/Libraries/GSF.TimeSeries/UI/WPF/Resources/StyleResource.xaml
@@ -336,8 +336,18 @@
         <Setter Property="Background" Value="Transparent"/>
     </Style>
 
+    <conv:MenuItemIconConverter x:Key="MenuItemIconConverter"/>
+
     <Style TargetType="{x:Type MenuItem}" x:Key="MenuItemStyle">
         <Setter Property="Command" Value="{Binding Command}" />
+        <Setter Property="Icon">
+            <Setter.Value>
+                <MultiBinding Converter="{StaticResource MenuItemIconConverter}">
+                    <Binding Path="Icon"/>
+                    <Binding Path="ExternalProcessPath"/>
+                </MultiBinding>
+            </Setter.Value>
+        </Setter>
         <Setter Property="FontWeight" Value="Bold"/>
         <Setter Property="HorizontalAlignment" Value="Left"/>
         <Setter Property="Margin" Value="1"/>