How can I serialize/deserialize a dictionary with custom keys using Json.Net?

Grx70's answer is good - just adding an alternative solution here. I ran into this problem in a Web API project where I wasn't calling SerializeObject but allowing the serialization to happen automagically.

This custom JsonConverter based on Brian Rogers' answer to a similar question did the trick for me:

public class DeepDictionaryConverter : JsonConverter
{
    public override bool CanConvert(Type objectType)
    {
        return (typeof(IDictionary).IsAssignableFrom(objectType) ||
                TypeImplementsGenericInterface(objectType, typeof(IDictionary<,>)));
    }

    private static bool TypeImplementsGenericInterface(Type concreteType, Type interfaceType)
    {
        return concreteType.GetInterfaces()
               .Any(i => i.IsGenericType && i.GetGenericTypeDefinition() == interfaceType);
    }

    public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
    {
        Type type = value.GetType();
        IEnumerable keys = (IEnumerable)type.GetProperty("Keys").GetValue(value, null);
        IEnumerable values = (IEnumerable)type.GetProperty("Values").GetValue(value, null);
        IEnumerator valueEnumerator = values.GetEnumerator();

        writer.WriteStartArray();
        foreach (object key in keys)
        {
            valueEnumerator.MoveNext();

            writer.WriteStartArray();
            serializer.Serialize(writer, key);
            serializer.Serialize(writer, valueEnumerator.Current);
            writer.WriteEndArray();
        }
        writer.WriteEndArray();
    }

    public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
    {
        throw new NotImplementedException();
    }
}

In my case, I was serializing a Dictionary<MyCustomType, int> property on a class where MyCustomType had properties like Name and Id. This is the result:

...
"dictionaryProp": [
    [
      {
        "name": "MyCustomTypeInstance1.Name",
        "description": null,
        "id": null
      },
      3
    ],
    [
      {
        "name": "MyCustomTypeInstance2.Name",
        "description": null,
        "id": null
      },
      2
    ]
]
...

This should do the trick:

Serialization:

JsonConvert.SerializeObject(expected.ToArray(), Formatting.Indented, jsonSerializerSettings);

By calling expected.ToArray() you're serializing an array of KeyValuePair<MyClass, object> objects rather than the dictionary.

Deserialization:

JsonConvert.DeserializeObject<KeyValuePair<IDataKey, object>[]>(output, jsonSerializerSettings).ToDictionary(kv => kv.Key, kv => kv.Value);

Here you deserialize the array and then retrieve the dictionary with .ToDictionary(...) call.

I'm not sure if the output meets your expectations, but surely it passes the equality assertion.