diff --git a/src/Discord.Net.Rest/Net/Converters/OptionalConverter.cs b/src/Discord.Net.Rest/Net/Converters/OptionalConverter.cs
index 18b2a9e1c..d3d6191c0 100644
--- a/src/Discord.Net.Rest/Net/Converters/OptionalConverter.cs
+++ b/src/Discord.Net.Rest/Net/Converters/OptionalConverter.cs
@@ -1,4 +1,4 @@
-using Newtonsoft.Json;
+using Newtonsoft.Json;
 using System;
 
 namespace Discord.Net.Converters
@@ -19,10 +19,18 @@ namespace Discord.Net.Converters
         public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
         {
             T obj;
+            // custom converters need to be able to safely fail; move this check in here to prevent wasteful casting when parsing primitives
             if (_innerConverter != null)
-                obj = (T)_innerConverter.ReadJson(reader, typeof(T), null, serializer);
+            {
+                object o = _innerConverter.ReadJson(reader, typeof(T), null, serializer);
+                if (o is Optional<T>)
+                    return o;
+
+                obj = (T)o;
+            }
             else
                 obj = serializer.Deserialize<T>(reader);
+
             return new Optional<T>(obj);
         }
 
diff --git a/src/Discord.Net.Rest/Net/Converters/UnixTimestampConverter.cs b/src/Discord.Net.Rest/Net/Converters/UnixTimestampConverter.cs
index d4660dc44..0b50cb166 100644
--- a/src/Discord.Net.Rest/Net/Converters/UnixTimestampConverter.cs
+++ b/src/Discord.Net.Rest/Net/Converters/UnixTimestampConverter.cs
@@ -1,4 +1,4 @@
-using System;
+using System;
 using Newtonsoft.Json;
 
 namespace Discord.Net.Converters
@@ -11,13 +11,18 @@ namespace Discord.Net.Converters
         public override bool CanRead => true;
         public override bool CanWrite => true;
 
+        // 1e13 unix ms = year 2286
+        // necessary to prevent discord.js from sending values in the e15 and overflowing a DTO
+        private const long MaxSaneMs = 1_000_000_000_000_0;
+
         public override object ReadJson(JsonReader reader, Type objectType, object existingValue, JsonSerializer serializer)
         {
-            // Discord doesn't validate if timestamps contain decimals or not
-            if (reader.Value is double d)
+            // Discord doesn't validate if timestamps contain decimals or not, and they also don't validate if timestamps are reasonably sized
+            if (reader.Value is double d && d < MaxSaneMs)
                 return new DateTimeOffset(1970, 1, 1, 0, 0, 0, 0, TimeSpan.Zero).AddMilliseconds(d);
-            long offset = (long)reader.Value;
-            return new DateTimeOffset(1970, 1, 1, 0, 0, 0, 0, TimeSpan.Zero).AddMilliseconds(offset);
+            else if (reader.Value is long l && l < MaxSaneMs)
+                return new DateTimeOffset(1970, 1, 1, 0, 0, 0, 0, TimeSpan.Zero).AddMilliseconds(l);
+            return Optional<DateTimeOffset>.Unspecified;
         }
 
         public override void WriteJson(JsonWriter writer, object value, JsonSerializer serializer)
@@ -25,4 +30,4 @@ namespace Discord.Net.Converters
             throw new NotImplementedException();
         }
     }
-}
\ No newline at end of file
+}