Connect accounts (Origin and Xbox Live)

You need to make a free silver Xbox Live account, and then connect to Live using your original Xbox game disc to trigger the update.

Are you on the original console the game was purchased on? Are you using the account the game was originally purchased with? Are you connected to Xbox LIVE when you try to play it?

Hey Invoked. As far as content licensing goes:

• The account who downloads the game can play it online and offline on the console it was
  originally downloaded on.
• Other accounts can play the game on the same console it was downloaded on when connected to Xbox Live. Not playable on other accounts when not connected to Live.
  
• The account who downloads the game can play it when connected to Live on a different console than the one it was
  originally downloaded on.
• On other consoles than the one the content was originally downloaded on, other profiles cannot play the downloaded content.
  

Live for the Original Xbox was shut down in 2010 so it's no longer possible to connect an account to it. You can still play original Xbox games on it.

Microsoft doesn't not give away free consoles.

I have tried to play a few of the originals without a connection of which it would not allow me to but once connected it was fine as these are tied to your xbox live account also.