diff --git a/tests/Avalonia.Markup.UnitTests/Parsers/ExpressionObserverBuilderTests_Property.cs b/tests/Avalonia.Markup.UnitTests/Parsers/ExpressionObserverBuilderTests_Property.cs
index a97c998264..4f7264f2f2 100644
--- a/tests/Avalonia.Markup.UnitTests/Parsers/ExpressionObserverBuilderTests_Property.cs
+++ b/tests/Avalonia.Markup.UnitTests/Parsers/ExpressionObserverBuilderTests_Property.cs
@@ -1,10 +1,10 @@
-using Avalonia.Data;
-using Avalonia.Markup.Parsers;
-using System;
+using System;
 using System.Collections.Generic;
 using System.Reactive.Linq;
-using System.Text;
+using System.Reactive.Subjects;
 using System.Threading.Tasks;
+using Avalonia.Data;
+using Avalonia.Markup.Parsers;
 using Xunit;
 
 namespace Avalonia.Markup.UnitTests.Parsers
@@ -38,5 +38,55 @@ namespace Avalonia.Markup.UnitTests.Parsers
 
             GC.KeepAlive(data);
         }
+
+        [Fact]
+        public void Should_Update_Value_After_Root_Changes()
+        {
+            var root = new { DataContext = new { Value = "Foo" } };
+            var subject = new Subject<object>();
+            var obs = ExpressionObserverBuilder.Build(subject, "DataContext.Value");
+
+            var values = new List<object>();
+            obs.Subscribe(v => values.Add(v));
+
+            subject.OnNext(root);
+            subject.OnNext(null);
+            subject.OnNext(root);
+
+            Assert.Equal("Foo", values[0]);
+
+            Assert.IsType<BindingNotification>(values[1]);
+            var bn = values[1] as BindingNotification;
+            Assert.Equal(AvaloniaProperty.UnsetValue, bn.Value);
+            Assert.Equal(BindingErrorType.Error, bn.ErrorType);
+
+            Assert.Equal(3, values.Count);
+            Assert.Equal("Foo", values[2]);
+        }
+
+        [Fact]
+        public void Should_Update_Value_After_Root_Changes_With_ComplexPath()
+        {
+            var root = new { DataContext = new { Foo = new { Value = "Foo" } } };
+            var subject = new Subject<object>();
+            var obs = ExpressionObserverBuilder.Build(subject, "DataContext.Foo.Value");
+
+            var values = new List<object>();
+            obs.Subscribe(v => values.Add(v));
+
+            subject.OnNext(root);
+            subject.OnNext(null);
+            subject.OnNext(root);
+
+            Assert.Equal("Foo", values[0]);
+
+            Assert.IsType<BindingNotification>(values[1]);
+            var bn = values[1] as BindingNotification;
+            Assert.Equal(AvaloniaProperty.UnsetValue, bn.Value);
+            Assert.Equal(BindingErrorType.Error, bn.ErrorType);
+
+            Assert.Equal(3, values.Count);
+            Assert.Equal("Foo", values[2]);
+        }
     }
 }