const
  c_URL = 'https://myserv.net:777/mydir';
  c_FileName = 'c:\123.txt';
  c_UserName = 'myname';
  c_Password = 'mypass';
var
  F: TFileStream;
  IdHTTP: TIdHTTP;
  IdSSLIOHandlerSocket: TIdSSLIOHandlerSocket;
  Response: string;
begin
  IdSSLIOHandlerSocket := TIdSSLIOHandlerSocket.Create(Application);
  IdSSLIOHandlerSocket.SSLOptions.Method := sslvSSLv3;

  IdHTTP := TIdHTTP.Create(Application);
  IdHTTP.IOHandler := IdSSLIOHandlerSocket;
  IdHTTP.Request.BasicAuthentication := true;
  IdHTTP.Request.UserName := c_UserName;
  IdHTTP.Request.Password := c_Password;

  F := TFileStream.Create(c_FileName, fmOpenRead + fmShareDenyNone);

  try
    try
      Response := IdHTTP.Post(c_URL, F);
    except
      on E: Exception do
        MessageBox(0, PChar(E.Message), 'Ашипка!', MB_ICONERROR or MB_SETFOREGROUND or MB_APPLMODAL);
    end;
  finally
    F.Free;
    IdSSLIOHandlerSocket.Free;
    IdHTTP.Free;
  end;
end;

HTTP/1.1 404 Not Found