diff --git a/src/System.Linq.Dynamic.Core/Parser/ExpressionParser.cs b/src/System.Linq.Dynamic.Core/Parser/ExpressionParser.cs
index 9069630e..a8f742e4 100644
--- a/src/System.Linq.Dynamic.Core/Parser/ExpressionParser.cs
+++ b/src/System.Linq.Dynamic.Core/Parser/ExpressionParser.cs
@@ -499,9 +499,21 @@ Expression ParseComparisonOperator()
                         }
                     }
 
+
                     if (!typesAreSameAndImplementCorrectInterface)
                     {
-                        CheckAndPromoteOperands(isEquality ? typeof(IEqualitySignatures) : typeof(IRelationalSignatures), op.Text, ref left, ref right, op.Pos);
+                        if (left.Type.GetTypeInfo().IsClass && right is ConstantExpression && HasImplicitConversion(left.Type, right.Type))
+                        {
+                            left = Expression.Convert(left, right.Type);
+                        }
+                        else if (right.Type.GetTypeInfo().IsClass && left is ConstantExpression && HasImplicitConversion(right.Type, left.Type))
+                        {
+                            right = Expression.Convert(right, left.Type);
+                        }
+                        else
+                        {
+                            CheckAndPromoteOperands(isEquality ? typeof(IEqualitySignatures) : typeof(IRelationalSignatures), op.Text, ref left, ref right, op.Pos);
+                        }
                     }
                 }
 
@@ -533,6 +545,13 @@ Expression ParseComparisonOperator()
             return left;
         }
 
+        private bool HasImplicitConversion(Type baseType, Type targetType)
+        {
+            return baseType.GetMethods(BindingFlags.Public | BindingFlags.Static)
+                .Where(mi => mi.Name == "op_Implicit" && mi.ReturnType == targetType)
+                .Any(mi => mi.GetParameters().FirstOrDefault()?.ParameterType == baseType);
+        }
+        
         private ConstantExpression ParseEnumToConstantExpression(int pos, Type leftType, ConstantExpression constantExpr)
         {
             return Expression.Constant(ParseConstantExpressionToEnum(pos, leftType, constantExpr), leftType);
diff --git a/test/System.Linq.Dynamic.Core.Tests/ExpressionTests.cs b/test/System.Linq.Dynamic.Core.Tests/ExpressionTests.cs
index af22335b..5fd4b004 100644
--- a/test/System.Linq.Dynamic.Core.Tests/ExpressionTests.cs
+++ b/test/System.Linq.Dynamic.Core.Tests/ExpressionTests.cs
@@ -1385,6 +1385,34 @@ public void ExpressionTests_SkipAndTake()
             }
         }
 
+        [Fact]
+        public void ExpressionTests_ImplicitCast()
+        {
+            //Arrange
+            Guid code1 = new Guid("651E08E3-85B1-42D1-80AF-68E28E2B7DA6");
+            Guid code2 = new Guid("6451FEB2-3226-41D0-961C-B72B7B5A0157");
+
+            var samples = User.GenerateSampleModels(3);
+            samples[0].State = new UserState() { StatusCode = code1, Description = "alive" };
+            samples[1].State = new UserState() { StatusCode = code2, Description = "deceased" };
+
+            //Act
+            string queryString = "State == @0";
+            IList<User> result = samples.AsQueryable().Where(queryString, code1).ToList();
+
+            string queryString2 = "@0 == State";
+            IList<User> result2 = samples.AsQueryable().Where(queryString2, code1).ToList();
+
+            //Assert
+            Assert.Equal(1, result.Count);
+            Assert.Equal(code1, result[0].State.StatusCode);
+            Assert.Equal("alive", result[0].State.Description);
+
+            Assert.Equal(1, result2.Count);
+            Assert.Equal(code1, result2[0].State.StatusCode);
+            Assert.Equal("alive", result2[0].State.Description);
+        }
+
         [Fact]
         public void ExpressionTests_StringCompare()
         {
diff --git a/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/User.cs b/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/User.cs
index c3f5c756..89cb22cd 100644
--- a/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/User.cs
+++ b/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/User.cs
@@ -14,6 +14,8 @@ public class User
 
         public UserProfile Profile { get; set; }
 
+        public UserState State { get; set; }
+
         public List<Role> Roles { get; set; }
 
         public bool TestMethod1()
@@ -62,4 +64,4 @@ public static IList<User> GenerateSampleModels(int total, bool allowNullableProf
             return list.ToArray();
         }
     }
-}
\ No newline at end of file
+}
diff --git a/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/UserState.cs b/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/UserState.cs
new file mode 100644
index 00000000..c22f6309
--- /dev/null
+++ b/test/System.Linq.Dynamic.Core.Tests/Helpers/Models/UserState.cs
@@ -0,0 +1,15 @@
+using System;
+using System.Collections.Generic;
+using System.Text;
+
+namespace System.Linq.Dynamic.Core.Tests.Helpers.Models
+{
+    public class UserState
+    {
+        public Guid StatusCode { get; set; }
+        public string Description { get; set; }
+
+        public static implicit operator Guid(UserState state)
+            => state?.StatusCode ?? Guid.Empty;
+    }
+}