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Hoping one day my python skills can accomplish stuff like that.Well, with Gmail you can filter out entries that have the wrong answers.
But I have no clue how they gonna "randomly" select e-mail winners. Not like they can assign a number to each e-mail and just use some random number generator. It's probably possible to write a script to gather all the e-mails and then assign numbers to them, but the fact that they went with an e-mail raffle suggests that they aren't that tech-savvy to be able to do that.