diff --git a/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.That.cs b/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.That.cs
index d0a9d9e004..2f4e7e3944 100644
--- a/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.That.cs
+++ b/test/UnitTests/TestFramework.UnitTests/Assertions/AssertTests.That.cs
@@ -1,6 +1,9 @@
 // Copyright (c) Microsoft Corporation. All rights reserved.
 // Licensed under the MIT license. See LICENSE file in the project root for full license information.
 
+using System.Linq.Expressions;
+using System.Reflection;
+
 using AwesomeAssertions;
 
 using TestFramework.ForTestingMSTest;
@@ -1277,4 +1280,72 @@ private readonly struct ValueBox(int value)
     {
         public int Value { get; } = value;
     }
+
+    private sealed class MutableContainer
+    {
+#pragma warning disable SA1401 // Fields should be private - intentional: this type tests Expression.Assign on nested members.
+        public MutableBox Inner = new() { Value = 0 };
+#pragma warning restore SA1401
+    }
+
+    private sealed class MutableBox
+    {
+#pragma warning disable SA1401 // Fields should be private - intentional: this type tests Expression.Assign on a field.
+        public int Value;
+#pragma warning restore SA1401
+    }
+
+    public void That_ManuallyConstructedAssignExpression_SurfacesRhsAndPreservesSideEffect()
+    {
+        // Construct: (container.Inner.Value = ComputeValue()) < 0   — fails, so message must
+        // include enough context for diagnosis AND the assignment side-effect must apply.
+        var container = new MutableContainer();
+        FieldInfo innerFi = typeof(MutableContainer).GetField(nameof(MutableContainer.Inner))!;
+        FieldInfo valueFi = typeof(MutableBox).GetField(nameof(MutableBox.Value))!;
+
+        MemberExpression innerAccess = Expression.Field(Expression.Constant(container), innerFi);
+        MemberExpression valueAccess = Expression.Field(innerAccess, valueFi);
+        MethodCallExpression rhs = Expression.Call(typeof(MutableBoxHelper).GetMethod(nameof(MutableBoxHelper.ComputeValue))!);
+        BinaryExpression assign = Expression.Assign(valueAccess, rhs);
+        BinaryExpression body = Expression.LessThan(assign, Expression.Constant(0));
+        var lambda = Expression.Lambda<Func<bool>>(body);
+
+        Action act = () => Assert.That(lambda);
+
+        AssertFailedException ex = act.Should().Throw<AssertFailedException>().Which;
+        // Assert on the method name only (not the parenthesized rendering) so that future
+        // renderer tweaks (e.g., dropping/adding parentheses for nullary calls) don't break
+        // this regression test.
+        ex.Message.Should().Contain(nameof(MutableBoxHelper.ComputeValue));
+        // The Inner member of the receiver chain should surface in the failure details.
+        ex.Message.Should().Contain("Inner");
+        // The assignment side-effect must apply.
+        container.Inner.Value.Should().Be(42);
+    }
+
+    // Regression: a member whose static type is Func/Action but whose runtime value is null should
+    // still appear in the failure details. Filtering must remain runtime-typed (via the cached
+    // value's GetType()) rather than static-typed at analysis time.
+    private sealed class HolderWithFuncField
+    {
+#pragma warning disable SA1401 // Fields should be private - intentional: test fixture exposing a delegate-typed field.
+        public Func<int>? Callback;
+#pragma warning restore SA1401
+    }
+
+    public void That_NullDelegateTypedMember_StillAppearsInDetails()
+    {
+        var holder = new HolderWithFuncField { Callback = null };
+
+        Action act = () => Assert.That(() => holder.Callback != null);
+
+        AssertFailedException ex = act.Should().Throw<AssertFailedException>().Which;
+        ex.Message.Should().Contain("Callback");
+        ex.Message.Should().Contain("null");
+    }
+}
+
+internal static class MutableBoxHelper
+{
+    public static int ComputeValue() => 42;
 }