1099 Season Starts Now, Not in January | Two Roads

1099 Season Starts Now, Not in January

The W-9 you don’t have in October is the 1099 you can’t send in January.

We know how frustrating it is. It’s the last week of January, the deadline is days away, and you’re texting a contractor you paid once back in March, asking for a tax ID they never sent. Multiply that by a dozen vendors, and January turns into a scavenger hunt.

The fix is simple: start now. Here’s a W-9 collection and vendor-review checklist built to go out in October, well ahead of the scramble.

Want this off your plate entirely? Schedule a call and we’ll run 1099 prep alongside you.

What’s Different This Year

Two things to know before you start:

  • The threshold went up. For payments made in 2026, you only file a 1099-NEC for contractors you paid $2,000 or more, up from $600. Fewer forms, but you still need to know who crossed the line.
  • The deadline is February 1, 2027. January 31 falls on a Sunday, so forms are due to contractors and the IRS the next business day. Filing 10 or more information returns in total, W-2s included? You must e-file them.

Your W-9 Collection Checklist

  • Pull a vendor payment report for January through September. This is your starting list.
  • Flag anyone missing a W-9. Send them a current Form W-9 with a clear due date.
  • Check the details. Legal name, tax ID, address, and tax classification should all be complete and match.
  • Use a secure upload, not email. A W-9 holds a Social Security number or EIN, so treat it like sensitive data.
  • Make it a rule going forward. No W-9, no first payment. Missing tax IDs can trigger 24% backup withholding, and no one wants that conversation.

Vendor records a mess? Our bookkeeping team can clean up your vendor list and keep W-9s organized all year.

Your Vendor-Review Checklist

Not every vendor gets a 1099. Sort your list now so January is just filing.

  • Usually need a 1099. Individuals, sole proprietors, partnerships, and most LLCs paid $2,000 or more for services.
  • Always check attorneys. Legal fees get a 1099 even when the firm is a corporation.
  • Usually skip. C and S corporations, and anyone you paid by credit card or a payment app like PayPal. Those payments are reported by the processor on a 1099-K.
  • Watch for split payments. If you paid a contractor partly by check or ACH and partly by card, only the check and ACH payments count toward the $2,000.
  • Note who’s close to $2,000. A December invoice can push a vendor over the line.

The Timeline That Beats the Scramble

  1. October: Send W-9 requests to every vendor missing one.
  2. November: Follow up on anything outstanding and finish your vendor review.
  3. December: Collect W-9s from any new vendors before their first payment.
  4. Early January: Close December’s books and confirm final totals per vendor.
  5. By February 1, 2027: File with the IRS and send copies to contractors.

Prefer to hand off the filing? Two Roads Tax can prepare and file your 1099s on time.

Final Thoughts

1099s aren’t hard. They’re just easy to put off. A few emails in October save you a week of chasing in January and give you a clean, confident start to tax season.

At Two Roads, we work alongside you to keep vendor records current all year, so 1099 season is a checkbox, not a crisis. Schedule a consultation and let’s get ahead of it together.