1099 Deadlines for Trucking Operators (and the One Most People Miss)

January 31 is the headline, but the contractor onboarding work starts in October. Here's the cadence.

If you pay a contractor more than $600 in a calendar year and they aren't incorporated, you owe them a 1099-NEC by January 31.

But the real work doesn't happen in January — it happens in October, when you should already be confirming W-9s, addresses, and payment totals.

The deadline most people miss isn't filing — it's collecting accurate W-9s before you cut the first check. A missing TIN at year-end becomes a $290 penalty per form, plus backup withholding paperwork.

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