diff --git a/src/FastExpressionCompiler/FastExpressionCompiler.cs b/src/FastExpressionCompiler/FastExpressionCompiler.cs
index 7a05bfcb..7db05d66 100644
--- a/src/FastExpressionCompiler/FastExpressionCompiler.cs
+++ b/src/FastExpressionCompiler/FastExpressionCompiler.cs
@@ -3878,17 +3878,13 @@ private static bool TryEmitConvert(UnaryExpression expr, ILGenerator il, ref Com
                         return il.EmitPopIfIgnoreResult(parent);
                     }
 
-                    if (targetType == typeof(object) && sourceType.IsValueType)
+                    if (sourceType.IsValueType && (targetType == typeof(object) ||
+                        underlyingNullableSourceType != null && !targetType.IsValueType &&
+                        (targetType.IsInterface || targetType.IsAssignableFrom(underlyingNullableSourceType))))
                     {
                         il.Demit(OpCodes.Box, sourceType);
-                        return il.EmitPopIfIgnoreResult(parent);
-                    }
-
-                    if (underlyingNullableSourceType != null && !targetType.IsValueType &&
-                        targetType.IsAssignableFrom(underlyingNullableSourceType))
-                    {
-                        il.Demit(OpCodes.Box, sourceType);
-                        il.Demit(OpCodes.Castclass, targetType);
+                        if (targetType.IsInterface && !targetType.IsAssignableFrom(underlyingNullableSourceType ?? sourceType))
+                            il.Demit(OpCodes.Castclass, targetType);
                         return il.EmitPopIfIgnoreResult(parent);
                     }
 
diff --git a/test/FastExpressionCompiler.TestsRunner.Net472/Program.cs b/test/FastExpressionCompiler.TestsRunner.Net472/Program.cs
index bd8124c2..253d48f4 100644
--- a/test/FastExpressionCompiler.TestsRunner.Net472/Program.cs
+++ b/test/FastExpressionCompiler.TestsRunner.Net472/Program.cs
@@ -35,6 +35,7 @@ static void RunLightExpressionTests(object state)
 
                 var t = (LightExpression.TestRun)state;
                 t.Run(new LightExpression.UnitTests.InvokeRefArgumentRegressionTests());
+                t.Run(new LightExpression.UnitTests.NullableBoxingRegressionTests());
                 t.Run(new LightExpression.UnitTests.RuntimeSwitchCaseRegressionTests());
                 t.Run(new LightExpression.UnitTests.StaticFieldAddressRegressionTests());
                 t.Run(new LightExpression.UnitTests.MultidimensionalGetStorageRegressionTests());
@@ -84,6 +85,7 @@ static void RunLightExpressionTests(object state)
 
             var fecTests = new TestRun();
             fecTests.Run(new InvokeRefArgumentRegressionTests());
+            fecTests.Run(new NullableBoxingRegressionTests());
             fecTests.Run(new LiftedRefConversionRegressionTests());
             fecTests.Run(new RuntimeSwitchCaseRegressionTests());
             fecTests.Run(new StaticFieldAddressRegressionTests());
diff --git a/test/FastExpressionCompiler.TestsRunner/Program.cs b/test/FastExpressionCompiler.TestsRunner/Program.cs
index 5dd58047..a5497178 100644
--- a/test/FastExpressionCompiler.TestsRunner/Program.cs
+++ b/test/FastExpressionCompiler.TestsRunner/Program.cs
@@ -64,6 +64,7 @@ public static void Main(string[] args)
             {
                 var ltStopwatch = Stopwatch.StartNew();
                 lt.Run(new LightExpression.UnitTests.InvokeRefArgumentRegressionTests());
+                lt.Run(new LightExpression.UnitTests.NullableBoxingRegressionTests());
                 lt.Run(new LightExpression.UnitTests.RuntimeSwitchCaseRegressionTests());
                 lt.Run(new LightExpression.UnitTests.StaticFieldAddressRegressionTests());
                 lt.Run(new LightExpression.UnitTests.MultidimensionalGetStorageRegressionTests());
@@ -110,6 +111,7 @@ public static void Main(string[] args)
 
             var stStopwatch = Stopwatch.StartNew();
             st.Run(new InvokeRefArgumentRegressionTests());
+            st.Run(new NullableBoxingRegressionTests());
             st.Run(new LiftedRefConversionRegressionTests());
             st.Run(new RuntimeSwitchCaseRegressionTests());
             st.Run(new StaticFieldAddressRegressionTests());
diff --git a/test/FastExpressionCompiler.UnitTests/NullableBoxingRegressionTests.cs b/test/FastExpressionCompiler.UnitTests/NullableBoxingRegressionTests.cs
new file mode 100644
index 00000000..143d2c04
--- /dev/null
+++ b/test/FastExpressionCompiler.UnitTests/NullableBoxingRegressionTests.cs
@@ -0,0 +1,68 @@
+using System;
+using System.Reflection;
+using SysExpr = System.Linq.Expressions.Expression;
+
+#if LIGHT_EXPRESSION
+using Expr = FastExpressionCompiler.LightExpression.Expression;
+namespace FastExpressionCompiler.LightExpression.UnitTests;
+#else
+using Expr = System.Linq.Expressions.Expression;
+namespace FastExpressionCompiler.UnitTests;
+#endif
+
+public struct NullableBoxingRegressionTests : ITestX
+{
+    public void Run(TestRun t)
+    {
+        Nullable_parameters_box_to_reference_types(t);
+        Nullable_constants_box_to_reference_types(t);
+        Nullable_locals_box_to_reference_types(t);
+
+    }
+
+    public void Nullable_parameters_box_to_reference_types(TestContext t) => Check(t, 0);
+    public void Nullable_constants_box_to_reference_types(TestContext t) => Check(t, 1);
+    public void Nullable_locals_box_to_reference_types(TestContext t) => Check(t, 2);
+
+    private static void Check(TestContext t, int shape)
+    {
+        Type[] types = { typeof(int), typeof(DayOfWeek), typeof(DateTime), typeof(Tagged) };
+        object[] values = { 42, DayOfWeek.Friday, DateTime.MinValue, new Tagged { Text = "value" } };
+        Type[] targets = { typeof(object), typeof(ValueType), typeof(Enum), typeof(IComparable), typeof(ITagged) };
+        for (var i = 0; i < types.Length; ++i)
+        foreach (var target in targets)
+        foreach (var value in new[] { null, values[i] })
+        foreach (var isChecked in new[] { false, true })
+        {
+            var nullable = typeof(Nullable<>).MakeGenericType(types[i]);
+            var parameter = SysExpr.Parameter(nullable);
+            System.Linq.Expressions.UnaryExpression conversion;
+            try { conversion = isChecked ? SysExpr.ConvertChecked(parameter, target) : SysExpr.Convert(parameter, target); }
+            catch (InvalidOperationException) { continue; }
+            var constant = SysExpr.Constant(value, nullable);
+            var body = shape == 1 ? conversion.Update(constant)
+                : shape == 2 ? (SysExpr)SysExpr.Block(new[] { parameter }, SysExpr.Assign(parameter, constant), conversion)
+                : conversion;
+            var expression = shape == 0 ? SysExpr.Lambda(body, parameter) : SysExpr.Lambda(body);
+            var fast = expression.FromSysExpression().CompileFast(true);
+            if (!t.IsNotNull(fast)) return;
+            var args = shape == 0 ? new[] { value } : Array.Empty<object>();
+            t.AreEqual(Invoke(expression.Compile(), args), Invoke(fast, args));
+        }
+    }
+
+    private static object Invoke(Delegate function, object[] arguments)
+    {
+        try { return function.DynamicInvoke(arguments); }
+        catch (TargetInvocationException e) { return e.InnerException.GetType(); }
+    }
+
+    public interface ITagged { }
+    public struct Tagged : ITagged { public string Text; }
+    public class Box { public int Value; }
+    public struct Convertible
+    {
+        public int Value;
+        public static implicit operator Box(Convertible value) => new Box { Value = value.Value };
+    }
+}