LDValue valueMessages = LDValue.arrayOf(
            LDValue.buildObject().put("content", "the user content").put("role", "user").build(),
            LDValue.buildObject().put("content", "the  system content").put("role", "system").build()
    );

    Iterable<Message> messages = valueMessages.valuesAs(new Message.MessageConverter());

import com.launchdarkly.sdk.LDValue;

public class Message {

    static class MessageConverter extends LDValue.Converter<Message> {
        @Override
        public LDValue fromType(Message message) {
            return LDValue.buildObject()
                    .put("content", message.getContent())
                    .put("role", message.getRole().toString())
                    .build();
        }

        @Override
        public Message toType(LDValue ldValue) {
            return new Message(ldValue.get("content").stringValue(), Role.getRole(ldValue.get("role").stringValue()));
        }
    }

    Message(String content, Role role) {
        this.content = content;
        this.role = role;
    }

    private String content;

    private Role role;

    public String getContent() {
        return content;
    }

    public Role getRole() {
        return role;
    }
}

public enum Role {
    USER("user"),
    SYSTEM("system"),
    ASSISTANT("assistant");

    private final String role;
    private Role(String role) {
        this.role = role;
    }
    public static Role getRole(String role) {
        switch (role) {
            case "user":
                return USER;
            case "system":
                return SYSTEM;
            case "assistant":
                return ASSISTANT;
            default:
                return null;
        }
    }

    @Override
    public String toString() {
        return role;
    }
}