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    <p>I think that is a bug in an older version of Json.NET. If you aren't already using the latest version, upgrade and try again.</p> <pre><code> public class UrlStatus { public int Status { get; set; } public string Url { get; set; } } [TestMethod] public void GenericDictionaryObject() { Dictionary&lt;string, object&gt; collection = new Dictionary&lt;string, object&gt;() { {"First", new UrlStatus{ Status = 404, Url = @"http://www.bing.com"}}, {"Second", new UrlStatus{Status = 400, Url = @"http://www.google.com"}}, {"List", new List&lt;UrlStatus&gt; { new UrlStatus {Status = 300, Url = @"http://www.yahoo.com"}, new UrlStatus {Status = 200, Url = @"http://www.askjeeves.com"} } } }; string json = JsonConvert.SerializeObject(collection, Formatting.Indented, new JsonSerializerSettings { TypeNameHandling = TypeNameHandling.All, TypeNameAssemblyFormat = FormatterAssemblyStyle.Simple }); Assert.AreEqual(@"{ ""$type"": ""System.Collections.Generic.Dictionary`2[[System.String, mscorlib],[System.Object, mscorlib]], mscorlib"", ""First"": { ""$type"": ""Newtonsoft.Json.Tests.Serialization.TypeNameHandlingTests+UrlStatus, Newtonsoft.Json.Tests"", ""Status"": 404, ""Url"": ""http://www.bing.com"" }, ""Second"": { ""$type"": ""Newtonsoft.Json.Tests.Serialization.TypeNameHandlingTests+UrlStatus, Newtonsoft.Json.Tests"", ""Status"": 400, ""Url"": ""http://www.google.com"" }, ""List"": { ""$type"": ""System.Collections.Generic.List`1[[Newtonsoft.Json.Tests.Serialization.TypeNameHandlingTests+UrlStatus, Newtonsoft.Json.Tests]], mscorlib"", ""$values"": [ { ""$type"": ""Newtonsoft.Json.Tests.Serialization.TypeNameHandlingTests+UrlStatus, Newtonsoft.Json.Tests"", ""Status"": 300, ""Url"": ""http://www.yahoo.com"" }, { ""$type"": ""Newtonsoft.Json.Tests.Serialization.TypeNameHandlingTests+UrlStatus, Newtonsoft.Json.Tests"", ""Status"": 200, ""Url"": ""http://www.askjeeves.com"" } ] } }", json); object c = JsonConvert.DeserializeObject(json, new JsonSerializerSettings { TypeNameHandling = TypeNameHandling.All, TypeNameAssemblyFormat = FormatterAssemblyStyle.Simple }); Assert.IsInstanceOfType(c, typeof(Dictionary&lt;string, object&gt;)); Dictionary&lt;string, object&gt; newCollection = (Dictionary&lt;string, object&gt;)c; Assert.AreEqual(3, newCollection.Count); Assert.AreEqual(@"http://www.bing.com", ((UrlStatus)newCollection["First"]).Url); List&lt;UrlStatus&gt; statues = (List&lt;UrlStatus&gt;) newCollection["List"]; Assert.AreEqual(2, statues.Count); } } </code></pre> <p>Edit, I just noticed you mentioned a list. TypeNameHandling should be set to All.</p> <p>Documentation: <a href="http://www.newtonsoft.com/json/help/html/SerializeTypeNameHandling.htm" rel="nofollow noreferrer"><strong>TypeNameHandling setting</strong></a></p>
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    1. POSerializing/Deserializing Dictionary of objects with JSON.NET
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    1. USJames Newton-King
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    1. COI'm using Json.NET 3.5 Release 8. I even downloaded the zip again to be sure.
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      1. USDan at Demand
    2. COJust tried the latest build 53965, still didn't work.
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    3. COTypeNameHandling = TypeNameHandling.All was the trick.
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