There are about 1,100 cookies on Cookie's table during his scenes.
Christmas with Cookie: Locked Away & Christmas with Cookie: The Watching were both filmed in the same day in about 10 hours total.
The pocket watch used in Cookie's segments is the exact same watch used in filming The Watching years earlier. Jason Morisette (director of The Watching) mailed it to Alan Maxson from Orlando Florida to use as a prop.