We plan to hold a raffle or drawing in which the winner will receive a two-year vehicle lease. I understand if it's a raffle, it's W-2G reportable, but a drawing is 1099 reportable. But do we report it all in the year it was won? Or over two years?

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We spoke with IRS information reporting specialist Mr. Siders (ID# 1002856356), who says that the recipient is winning once, not over two years. So the full value of the prize (lease) should be reported once, for the year the prize is awarded. You are correct that if it is a raffle, report on W-2G; if a drawing, on 1099-MISC.

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