How to force TypeNameHandling.All $type on every boxed element in collections in Newtonsoft Json.Net

Question

I am working on migrating old legacy code from BinaryFormatter usage to Json serialization. One of the challenges is handling serialization for untyped collections, arrays, List, Dictionary etc...

I tried setting TypeNameHandling = TypeNameHandling.All, but for elements/items that are boxed ; structs or enums, Json.Net converts them to string, and Int64 and essentially lose their type. I am wondering if anyone has written a converter or an extension to work with this case. I am not sure if this is a bug or an intended behavior.

Instead of

List<Object> { Point, Enum} == > { "111,222",2}

maybe something like this

{
    [{
            "$type": "System.Drawing.Point",
            "x": 111
            "y": 222
        }, {
            "$type": "System.Windows.WindowState",
            "value": 2
        }
    ]
}

Example

I took this example and modified it to a similar case using IList. https://www.newtonsoft.com/json/help/html/SerializeTypeNameHandling.htm

I kept the class names even though they don't make sense for ease of comparison with the original code. I can copy the code and run the code below in LinqPad.

void Main()
{
    var stockholder = new Stockholder
    {
        FullName = "Steve Stockholder",
        Businesses = new List<object>
                 {
                     new Hotel
                     {
                         Name = "Hudson Hotel",
                         Stars = 4
                    },
                    new System.Drawing.Point(1000,1),
                    WindowState.Maximized

                }
    };

    string jsonTypeNameAll = Newtonsoft.Json.JsonConvert.SerializeObject(stockholder, Newtonsoft.Json.Formatting.Indented, new JsonSerializerSettings
    {
        TypeNameHandling = TypeNameHandling.All
    });

    Console.WriteLine(jsonTypeNameAll);

    string jsonTypeNameAuto = Newtonsoft.Json.JsonConvert.SerializeObject(stockholder, Newtonsoft.Json.Formatting.Indented, new JsonSerializerSettings
    {
        TypeNameHandling = TypeNameHandling.Auto
    });

    Console.WriteLine(jsonTypeNameAuto);

    Stockholder newStockholder = JsonConvert.DeserializeObject<Stockholder>(jsonTypeNameAuto, new JsonSerializerSettings
    {
        TypeNameHandling = TypeNameHandling.Auto
    });

    Console.WriteLine(newStockholder.Businesses[0].GetType().Name);
    Console.WriteLine(newStockholder.Businesses[1].GetType().Name);
    Console.WriteLine(newStockholder.Businesses[2].GetType().Name);
}

public abstract class Business
{
    public string Name { get; set; }
}

public class Hotel : Business
{
    public int Stars { get; set; }
}

public class Stockholder
{
    public string FullName { get; set; }
    public IList<object> Businesses { get; set; }
}

Output

{
  "$type": "UserQuery+Stockholder, query_avpnnz",
  "FullName": "Steve Stockholder",
  "Businesses": {
    "$type": "System.Collections.Generic.List`1[[System.Object, mscorlib]], mscorlib",
    "$values": [
      {
        "$type": "UserQuery+Hotel, query_avpnnz",
        "Stars": 4,
        "Name": "Hudson Hotel"
      },
      "1000, 1",
      2
    ]
  }
}
{
  "FullName": "Steve Stockholder",
  "Businesses": [
    {
      "$type": "UserQuery+Hotel, query_avpnnz",
      "Stars": 4,
      "Name": "Hudson Hotel"
    },
    "1000, 1",
    2
  ]
}
Hotel
String
Int64

Expected

{
    "$type": "UserQuery+Stockholder, query_avpnnz",
    "FullName": "Steve Stockholder",
    "Businesses": {
        "$type": "System.Collections.Generic.List`1[[System.Object, mscorlib]], mscorlib",
        "$values": [{
                "$type": "UserQuery+Hotel, query_avpnnz",
                "Stars": 4,
                "Name": "Hudson Hotel"
            }, {
                "$type": "System.Drawing.Point",
                "x": 1000
                "y": 1
            }, {
                "$type": "System.Windows.WindowState",
                "value": 2
            }
        ]
    }
}