1099 Filing

Year-end contractor reporting

1099 Filing

If you pay independent contractors, you are required to report what you paid them — and the deadline lands at the end of January, on top of everything else that year-end already brings.

The division of labor is simple. You collect a W-9 from each contractor you hire — they are your people, and the request lands better coming from you. We track what each one was paid across the year, tell you who is missing a W-9 while there is still time to ask, and prepare and file the 1099s in January.

You probably need help with 1099s if

• You pay subcontractors and are unsure which of them need a 1099
• You are chasing contractors for W-9s in January instead of at hire
• You have missed a 1099 deadline or paid a late-filing penalty
• You are not certain whether someone should get a 1099 or a W-2
• Contractor payments are scattered across accounts and hard to total
• You pay contractors several different ways and lose track

How 1099 filing works

1. You collect the W-9s

   Ask every contractor for a W-9 before you pay them the first time. That one habit is what makes January easy. It has to come from you rather than from us — they are your contractors, and a request from their own client gets answered far more reliably than one from a bookkeeper they have never met. Send them to us as you get them and we will keep them on file.

2. Classification check

   Some contractors should be employees, and some payees do not need a 1099 at all. We sort out who is who during the year rather than at the deadline, when getting it wrong becomes expensive.

3. Year-round tracking

   Contractor payments are tracked by payee as they happen, across every account you pay from, so the year-end total is a report you pull rather than a reconstruction you attempt.

4. Preparation and your review

   We prepare the 1099s and send them to you before anything is filed. Corrections are far cheaper before submission than after.

5. Filing and distribution

   Filed with the IRS and distributed to your contractors ahead of the January 31 deadline.

Common questions

• Which contractors actually need a 1099?

  Generally, unincorporated contractors you paid $2,000 or more during the year for services (the new federal threshold starting with 2026 payments, filed in 2027; it was $600 for prior years). There are exceptions running in both directions, which is exactly why classification and up-front W-9 collection matter more than the filing itself.

• When is the deadline?

  1099-NEC forms are due to both the recipient and the IRS by January 31. It is a hard deadline with penalties attached, and it does not move because you had a busy month.

• What if I never collected a W-9?

  We will tell you exactly which contractors are missing one so you can request it, and we will do that well before January rather than during it. Chasing someone down after they have moved on is harder, but it is a solvable problem and considerably better than filing without the information or not filing at all.

• What if I have already missed a deadline?

  A late filing is still worth making. Penalties scale with how late it is, so getting current quickly costs less than waiting. We will get the outstanding filings caught up.

• Do you still handle 1099s if my contractors are paid through Gusto?

  Yes. We handle 1099 filing directly either way. Having contractor payments already tracked in one place just makes it simpler.