For 2016 and later years the penalty for not filing a Form 1099 when you should have is $250 per form. If you file it late the penalty is $15 if filed within 30 days after the due date. If 1099 is not filed for someone, and it can be shown that not doing so was intentional, the fine is $530 per 1099. The due date for 2017 Form 1099’s is January 31, 2018.
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