diff --git a/src/Avalonia.Base/Data/Core/Plugins/ObservableStreamPlugin.cs b/src/Avalonia.Base/Data/Core/Plugins/ObservableStreamPlugin.cs
index 14ca8ee79e..c41097c274 100644
--- a/src/Avalonia.Base/Data/Core/Plugins/ObservableStreamPlugin.cs
+++ b/src/Avalonia.Base/Data/Core/Plugins/ObservableStreamPlugin.cs
@@ -2,6 +2,9 @@
 // Licensed under the MIT license. See licence.md file in the project root for full license information.
 
 using System;
+using System.Linq;
+using System.Reactive.Linq;
+using System.Reflection;
 
 namespace Avalonia.Data.Core.Plugins
 {
@@ -10,12 +13,19 @@ namespace Avalonia.Data.Core.Plugins
     /// </summary>
     public class ObservableStreamPlugin : IStreamPlugin
     {
+        static MethodInfo observableSelect;
+
         /// <summary>
         /// Checks whether this plugin handles the specified value.
         /// </summary>
         /// <param name="reference">A weak reference to the value.</param>
         /// <returns>True if the plugin can handle the value; otherwise false.</returns>
-        public virtual bool Match(WeakReference reference) => reference.Target is IObservable<object>;
+        public virtual bool Match(WeakReference reference)
+        {
+            return reference.Target.GetType().GetInterfaces().Any(x =>
+              x.IsGenericType &&
+              x.GetGenericTypeDefinition() == typeof(IObservable<>));
+        }
 
         /// <summary>
         /// Starts producing output based on the specified value.
@@ -26,7 +36,69 @@ namespace Avalonia.Data.Core.Plugins
         /// </returns>
         public virtual IObservable<object> Start(WeakReference reference)
         {
-            return reference.Target as IObservable<object>;
+            var target = reference.Target;
+
+            // If the observable returns a reference type then we can cast it.
+            if (target is IObservable<object> result)
+            {
+                return result;
+            };
+
+            // If the observable returns a value type then we need to call Observable.Select on it.
+            // First get the type of T in `IObservable<T>`.
+            var sourceType = reference.Target.GetType().GetInterfaces().First(x =>
+                  x.IsGenericType &&
+                  x.GetGenericTypeDefinition() == typeof(IObservable<>)).GetGenericArguments()[0];
+
+            // Get the Observable.Select method.
+            var select = GetObservableSelect(sourceType);
+
+            // Make a Box<> delegate of the correct type.
+            var funcType = typeof(Func<,>).MakeGenericType(sourceType, typeof(object));
+            var box = GetType().GetMethod(nameof(Box), BindingFlags.Static | BindingFlags.NonPublic)
+                .MakeGenericMethod(sourceType)
+                .CreateDelegate(funcType);
+
+            // Call Observable.Select(target, box);
+            return (IObservable<object>)select.Invoke(
+                null,
+                new object[] { target, box });
+        }
+
+        private static MethodInfo GetObservableSelect(Type source)
+        {
+            return GetObservableSelect().MakeGenericMethod(source, typeof(object));
         }
+
+        private static MethodInfo GetObservableSelect()
+        {
+            if (observableSelect == null)
+            {
+                observableSelect = typeof(Observable).GetRuntimeMethods().First(x =>
+                {
+                    if (x.Name == nameof(Observable.Select) &&
+                        x.ContainsGenericParameters &&
+                        x.GetGenericArguments().Length == 2)
+                    {
+                        var parameters = x.GetParameters();
+
+                        if (parameters.Length == 2 &&
+                            parameters[0].ParameterType.IsConstructedGenericType &&
+                            parameters[0].ParameterType.GetGenericTypeDefinition() == typeof(IObservable<>) &&
+                            parameters[1].ParameterType.IsConstructedGenericType &&
+                            parameters[1].ParameterType.GetGenericTypeDefinition() == typeof(Func<,>))
+                        {
+                            return true;
+                        }
+                    }
+
+                    return false;
+                });
+            }
+
+            return observableSelect;
+        }
+
+        private static object Box<T>(T value) => (object)value;
     }
 }