diff --git a/src/SIL.Machine.AspNetCore/Services/ClearMLService.cs b/src/SIL.Machine.AspNetCore/Services/ClearMLService.cs
index e783f3b54..02e7b5e66 100644
--- a/src/SIL.Machine.AspNetCore/Services/ClearMLService.cs
+++ b/src/SIL.Machine.AspNetCore/Services/ClearMLService.cs
@@ -10,7 +10,7 @@ public class ClearMLService : IClearMLService
         new()
         {
             PropertyNamingPolicy = JsonNamingPolicy,
-            Converters = { new JsonStringEnumConverter(JsonNamingPolicy) }
+            Converters = { new CustomEnumConverterFactory(JsonNamingPolicy) }
         };
 
     private readonly IClearMLAuthenticationService _clearMLAuthService;
diff --git a/src/SIL.Machine.AspNetCore/Usings.cs b/src/SIL.Machine.AspNetCore/Usings.cs
index f876e437a..bd130ee4a 100644
--- a/src/SIL.Machine.AspNetCore/Usings.cs
+++ b/src/SIL.Machine.AspNetCore/Usings.cs
@@ -8,6 +8,7 @@
 global using System.Runtime.CompilerServices;
 global using System.Security.Cryptography;
 global using System.Text;
+global using System.Text.Encodings.Web;
 global using System.Text.Json;
 global using System.Text.Json.Nodes;
 global using System.Text.Json.Serialization;
diff --git a/src/SIL.Machine.AspNetCore/Utils/CustomEnumConverterFactory.cs b/src/SIL.Machine.AspNetCore/Utils/CustomEnumConverterFactory.cs
new file mode 100644
index 000000000..b398ffdff
--- /dev/null
+++ b/src/SIL.Machine.AspNetCore/Utils/CustomEnumConverterFactory.cs
@@ -0,0 +1,158 @@
+public sealed class CustomEnumConverterFactory : JsonConverterFactory
+{
+    private readonly JsonNamingPolicy _namingPolicy;
+
+    public CustomEnumConverterFactory(JsonNamingPolicy namingPolicy)
+    {
+        _namingPolicy = namingPolicy;
+    }
+
+    public override bool CanConvert(Type typeToConvert) => typeToConvert.IsEnum;
+
+    public override JsonConverter CreateConverter(Type typeToConvert, JsonSerializerOptions options)
+    {
+        object[]? knownValues = null;
+
+        if (typeToConvert == typeof(BindingFlags))
+        {
+            knownValues = new object[] { BindingFlags.CreateInstance | BindingFlags.DeclaredOnly };
+        }
+
+        return (JsonConverter)
+            Activator.CreateInstance(
+                typeof(CustomEnumConverter<>).MakeGenericType(typeToConvert),
+                BindingFlags.Instance | BindingFlags.Public,
+                binder: null,
+                args: new object?[] { _namingPolicy, options, knownValues },
+                culture: null
+            )!;
+    }
+}
+
+public sealed class CustomEnumConverter<T> : JsonConverter<T>
+    where T : Enum
+{
+    private readonly JsonNamingPolicy _namingPolicy;
+
+    private readonly Dictionary<string, T> _readCache = new();
+    private readonly Dictionary<T, JsonEncodedText> _writeCache = new();
+
+    // This converter will only support up to 64 enum values (including flags) on serialization and deserialization
+    private const int NameCacheLimit = 64;
+
+    private const string ValueSeparator = ", ";
+
+    public CustomEnumConverter(JsonNamingPolicy namingPolicy, JsonSerializerOptions options, object[]? knownValues)
+    {
+        _namingPolicy = namingPolicy;
+
+        bool continueProcessing = true;
+        for (int i = 0; i < knownValues?.Length; i++)
+        {
+            if (!TryProcessValue((T)knownValues[i]))
+            {
+                continueProcessing = false;
+                break;
+            }
+        }
+
+        if (continueProcessing)
+        {
+            Array values = Enum.GetValues(typeof(T));
+
+            for (int i = 0; i < values.Length; i++)
+            {
+                T value = (T)values.GetValue(i)!;
+
+                if (!TryProcessValue(value))
+                {
+                    break;
+                }
+            }
+        }
+
+        bool TryProcessValue(T value)
+        {
+            if (_readCache.Count == NameCacheLimit)
+            {
+                Debug.Assert(_writeCache.Count == NameCacheLimit);
+                return false;
+            }
+
+            FormatAndAddToCaches(value, options.Encoder);
+            return true;
+        }
+    }
+
+    public override T Read(ref Utf8JsonReader reader, Type typeToConvert, JsonSerializerOptions options)
+    {
+        string? json;
+
+        if (
+            reader.TokenType != JsonTokenType.String
+            || (json = reader.GetString()) == null
+            || !_readCache.TryGetValue(json, out T? value)
+        )
+        {
+            throw new JsonException();
+        }
+
+        return value;
+    }
+
+    public override void Write(Utf8JsonWriter writer, T value, JsonSerializerOptions options)
+    {
+        if (!_writeCache.TryGetValue(value, out JsonEncodedText formatted))
+        {
+            if (_writeCache.Count == NameCacheLimit)
+            {
+                Debug.Assert(_readCache.Count == NameCacheLimit);
+                throw new ArgumentOutOfRangeException();
+            }
+
+            formatted = FormatAndAddToCaches(value, options.Encoder);
+        }
+
+        writer.WriteStringValue(formatted);
+    }
+
+    private JsonEncodedText FormatAndAddToCaches(T value, JavaScriptEncoder? encoder)
+    {
+        (string valueFormattedToStr, JsonEncodedText valueEncoded) = FormatEnumValue(
+            value.ToString(),
+            _namingPolicy,
+            encoder
+        );
+        _readCache[valueFormattedToStr] = value;
+        _writeCache[value] = valueEncoded;
+        return valueEncoded;
+    }
+
+    private ValueTuple<string, JsonEncodedText> FormatEnumValue(
+        string value,
+        JsonNamingPolicy namingPolicy,
+        JavaScriptEncoder? encoder
+    )
+    {
+        string converted;
+
+        if (!value.Contains(ValueSeparator))
+        {
+            converted = namingPolicy.ConvertName(value);
+        }
+        else
+        {
+            // todo: optimize implementation here by leveraging https://github.com/dotnet/runtime/issues/934.
+            string[] enumValues = value.Split(ValueSeparator);
+
+            for (int i = 0; i < enumValues.Length; i++)
+            {
+                enumValues[i] = namingPolicy.ConvertName(enumValues[i]);
+            }
+
+            converted = string.Join(ValueSeparator, enumValues);
+        }
+
+        return (converted, JsonEncodedText.Encode(converted, encoder));
+    }
+}