Streamline Your 1099 Filing in 2026

When you see a blog post about 1099s, W-2s, 401(k)s, 1120s, it probably sounds more like an anxiety-inducing random-number generator than something important.

Good news is, we’re here to break down 1099s for you.

TLDR:

• File a 1099-NEC for any non-employee vendor paid $2,000 or more in 2026, up from $600.
• Payments made through PayPal, Venmo, Stripe, or credit card are exempt; those platforms report independently.
• The IRS FIRE e-filing system shuts down at end of 2026; apply for an IRIS TCC now, as it takes up to 45 days.
• Your January 31 deadline is firm; missing it triggers IRS penalties, so collect W-9s from vendors before year-end.
• Puzzle auto-detects vendors likely needing 1099s and gives you a single view across all payment methods.

What vendors require 1099s?

You need to file a Form 1099-NEC if any vendors meet these criteria:

• They provide services (not goods) as a non-employee, including freelancers, independent contractors, and attorneys.
• You have paid them $2,000 or more during the calendar year (ending December 31). The One Big Beautiful Bill Act raised this threshold from $600 to $2,000 starting in 2026.
• They are an LLC, partnership, or sole proprietorship (not a C-Corp or S-Corp). Exception: Attorneys require 1099s regardless of entity type.
• Payments were not made via a “payment settlement entity” like PayPal, Venmo, or Stripe.

What about PayPal, Venmo, or credit cards?

If you pay a contractor via PayPal, Venmo, Stripe, or credit card, you do not need to file a 1099-NEC with them. These payment settlement entities are responsible for their own reporting. The One Big Beautiful Bill Act (2025) permanently restored the federal 1099-K reporting threshold for these platforms to more than $20,000 and 200 transactions per year, so most contractors paid this way won't trigger a platform-issued 1099-K either.

What information do I need?

To fill out Form 1099, collect this from each vendor (keeping clean accounts payable records makes this easier):

• Name
• Mailing location
• Entity type
• Taxpayer ID number - SSN or EIN
• Email (if sending digitally)

Request vendors complete an IRS Form W-9 to provide this. Just email them the link or PDF version. We also created a tracking template to help.

Tax deadlines for Delaware C corps

If you run a startup and file your taxes in Delaware…

Delaware C corps face a unique set of filing obligations: franchise tax, state taxes, and federal returns all land on different dates and carry separate penalties for missing them. Screenshot this and add these tax deadlines to your calendar.

Key tax deadlines to track

Missing filing deadlines usually results in annoying penalties.

What's new for 2026 filings

Two filing changes are worth flagging as you prepare for the January 31, 2027 deadline, and if your month-end close is already tight, getting ahead of these now matters.

The IRS is shutting down FIRE. If you e-file 1099s through the IRS's FIRE system, it goes offline for good at the end of 2026. IRIS (the IRS's new intake system) is its permanent replacement. To file electronically through IRIS, you need a Transmitter Control Code (TCC), and the IRS says the application can take up to 45 days to process. If you haven't applied yet, do it now. Businesses required to file 10 or more information returns must e-file, so this isn't optional for most startups.

New tip and overtime fields on 1099-NEC. The IRS updated Form 1099-NEC for 2026 to allow reporting of cash tips, Treasury Tipped Occupation Codes, and overtime compensation. See the IRS instructions for Forms 1099-MISC and 1099-NEC for details on the new boxes. If any of your contractors received tips or overtime-equivalent payments, you'll need to break those out separately. Clean vendor records now save a scramble in January.

How does Puzzle help?

Puzzle guides you in identifying vendors needing 1099s:

• Single view of all vendors in one place, regardless of payment method - peace of mind you’re not forgetting anything
• Auto-detection of vendors more likely to need 1099s based on spending patterns
• Review process to confirm and track 1099 vendors
• Instructions for next steps

Frequently Asked Questions

Who needs to file a 1099-NEC?

You need to file a 1099-NEC for any vendor who: provides services (not goods) as a non-employee, is structured as an LLC, partnership, or sole proprietorship (attorneys require one regardless of entity type), and received $2,000 or more from you during the calendar year. This $2,000 threshold applies starting in 2026, raised from the previous $600 limit by the One Big Beautiful Bill Act. Payments made through PayPal, Venmo, Stripe, or credit card are exempt; those platforms handle their own reporting.

What's the deadline to file 1099s?

The deadline to file 1099 forms is January 31. For 2026 tax year filings, that means January 31, 2027. Missing this deadline typically results in IRS penalties, so it's worth getting vendor information (name, mailing location, entity type, and taxpayer ID) well before year-end.

How do I collect the information I need from vendors?

Ask each vendor to complete an IRS Form W-9 before you pay them. The W-9 captures their legal name, mailing location, entity type, and taxpayer ID (SSN or EIN). Sending them the IRS link or a PDF is all it takes. Keeping clean accounts payable records throughout the year makes this noticeably easier come January.

Do I need to file a 1099 if I pay contractors through PayPal or Venmo?

No. If you pay a contractor through a payment settlement entity (PayPal, Venmo, Stripe, or a credit card), you are not required to file a 1099-NEC for those payments. The platform is responsible for its own reporting. The One Big Beautiful Bill Act (2025) permanently set the federal 1099-K threshold for these platforms at more than $20,000 and 200 transactions per year, so most contractors paid this way won't receive a platform-issued 1099-K either.

What's changing for 2026 1099 filings?

Two notable changes apply: First, the IRS is shutting down its FIRE e-filing system at the end of 2026. Its replacement, IRIS, requires a Transmitter Control Code (TCC) that can take up to 45 days to obtain. Apply now if you file 10 or more information returns (e-filing is mandatory at that threshold). Second, Form 1099-NEC has new fields for cash tips, Treasury Tipped Occupation Codes, and overtime compensation. If any contractors received tips or overtime-equivalent payments, those must be broken out separately.

How to file your 1099s

File with both the IRS and each vendor. For e-filing, paid portals like Track1099 charge a few dollars per form. Free options include the IRS's own IRIS portal (the replacement for the retiring FIRE system) and Tax1099's free tier for small volumes. You can also mail paper copies, though e-filing is mandatory if you submit 10 or more information returns.

Need help or if you’re behind on your accounting and bookkeeping this year? Reach out to us in-app or get started here.