diff --git a/src/Compilers/CSharp/Portable/FlowAnalysis/NullableWalker.cs b/src/Compilers/CSharp/Portable/FlowAnalysis/NullableWalker.cs
index 2ef8a8f7ad491..4643ad1cb71e0 100644
--- a/src/Compilers/CSharp/Portable/FlowAnalysis/NullableWalker.cs
+++ b/src/Compilers/CSharp/Portable/FlowAnalysis/NullableWalker.cs
@@ -3160,11 +3160,18 @@ void visitOperandConversion(
                     ParameterSymbol parameter,
                     TypeWithState operandType)
                 {
+                    TypeWithAnnotations targetTypeWithNullability = parameter.TypeWithAnnotations;
+
+                    if (isLifted && targetTypeWithNullability.Type.IsNonNullableValueType())
+                    {
+                        targetTypeWithNullability = TypeWithAnnotations.Create(MakeNullableOf(targetTypeWithNullability));
+                    }
+
                     _ = VisitConversion(
                         expr as BoundConversion,
                         operand,
                         conversion,
-                        parameter.TypeWithAnnotations,
+                        targetTypeWithNullability,
                         operandType,
                         checkConversion: true,
                         fromExplicitCast: false,
@@ -7581,7 +7588,8 @@ private void ReportNullabilityMismatchInArgument(SyntaxNode argument, TypeSymbol
         private void ReportNullabilityMismatchInArgument(Location argument, TypeSymbol argumentType, ParameterSymbol parameterOpt, TypeSymbol parameterType, bool forOutput)
         {
             ReportDiagnostic(forOutput ? ErrorCode.WRN_NullabilityMismatchInArgumentForOutput : ErrorCode.WRN_NullabilityMismatchInArgument,
-                argument, argumentType, parameterType,
+                argument, argumentType,
+                parameterOpt?.Type.IsNonNullableValueType() == true && parameterType.IsNullableType() ? parameterOpt.Type : parameterType, // Compensate for operator lifting
                 GetParameterAsDiagnosticArgument(parameterOpt),
                 GetContainingSymbolAsDiagnosticArgument(parameterOpt));
         }
diff --git a/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs b/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
index f5ff53e45930f..3a2e7f4a19ae6 100644
--- a/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
+++ b/src/Compilers/CSharp/Test/Semantic/Semantics/NullableReferenceTypesTests.cs
@@ -121902,6 +121902,92 @@ static void M<T>(
             comp.VerifyDiagnostics();
         }
 
+        [Fact]
+        [WorkItem(35057, "https://github.com/dotnet/roslyn/issues/39361")]
+        public void Operator_11()
+        {
+            var source =
+@"
+#nullable enable
+
+using System;
+
+struct S    
+{
+    public static implicit operator DateTime?(S? value) => default;
+
+    bool M1(S? x1, DateTime y1)
+    {
+        return x1 == y1;
+    }
+
+    bool M2(DateTime? x2, DateTime y2)
+    {
+        return x2 == y2;
+    }
+
+    bool M3(DateTime x3, DateTime? y3)
+    {
+        return x3 == y3;
+    }
+
+    bool M4(DateTime x4, S? y4)
+    {
+        return x4 == y4;
+    }
+
+    bool M5(DateTime? x5, DateTime? y5)
+    {
+        return x5 == y5;
+    }
+
+    bool M6(S? x6, DateTime? y6)
+    {
+        return x6 == y6;
+    }
+
+    bool M7(DateTime? x7, S? y7)
+    {
+        return x7 == y7;
+    }
+
+    bool M8(DateTime x8, S y8)
+    {
+        return x8 == y8;
+    }
+
+    bool M9(S x9, DateTime y9)
+    {
+        return x9 == y9;
+    }
+}
+";
+            var comp = CreateCompilation(source);
+            comp.VerifyDiagnostics();
+        }
+
+        [Fact]
+        [WorkItem(35057, "https://github.com/dotnet/roslyn/issues/39361")]
+        public void Operator_12()
+        {
+            var source =
+@"
+#nullable enable
+
+struct S    
+{
+    public static bool operator-(S value) => default;
+
+    bool? M1(S? x1)
+    {
+        return -x1;
+    }
+}
+";
+            var comp = CreateCompilation(source);
+            comp.VerifyDiagnostics();
+        }
+
         [Theory]
         [InlineData("object.Equals")]
         [InlineData("object.ReferenceEquals")]