An example console app in C# looping a ogg file to a Shout cast server

shout-cast.cs

using System.Net.Sockets;
using System.Text;

namespace ConsoleApp1
{
    internal class Program
    {
        private const string clientId = "source";
        private const string clientSecret = "hackme";
        private const string clientName = "😂 stream";
        private const string clientDescription = "This is just a simple 😀 stream";
        private const string clientUrl = "http://example.org";
        private const string clientGenre = "😎";

        static void Main(string[] args)
        {
            using Stream s = File.OpenRead(args.First());

            var client = new TcpClient();

            client.Connect("localhost", 8000);

            var authenticationString = $"{clientId}:{clientSecret}";
            var base64EncodedAuthenticationString = Convert
                .ToBase64String(ASCIIEncoding.ASCII.GetBytes(authenticationString));

            var request = $@"PUT /stream.ogg HTTP/1.1
Host: localhost:8000
Authorization: Basic {base64EncodedAuthenticationString}
Accept: */*
Transfer-Encoding: chunked
Content-Type: audio/ogg
Ice-Public: 1
Ice-Name: {clientName}
Ice-Description: {clientDescription}
Ice-URL: {clientUrl}
Ice-Genre: {clientGenre}
Expect: 100-continue

";

            using var stream = client.GetStream();

            stream.Write(Encoding.UTF8.GetBytes(request));

            byte[] buffer = new byte[4096];
            var read = stream.Read(buffer);

            var response = Encoding.UTF8.GetString(buffer);
            Console.WriteLine(response.Trim());

            if (!response.StartsWith("HTTP/1.1 100 Continue"))
            {
                Console.WriteLine("Unexpected response:");
                Console.WriteLine(response);

                return;
            }

            do
            {
                byte[] fileBuffer = new byte[4096];
                var fileRead = s.Read(fileBuffer);
                if (fileRead == 0)
                {
                    Console.WriteLine("Restarting song");
                    s.Position = 0;
                    fileRead = s.Read(fileBuffer);
                }

                stream.Write(fileBuffer, 0, fileRead);

                Thread.Sleep(50);
            } while (true);
        }
    }
}