Guidelines for a successful 1099 season

Use this page as a working checklist for the weeks before you file 1099-NEC or 1099-MISC (Box 6) forms with Wingspan. Each item links to the page that covers it in detail.

This isn't tax or legal advice. Consult a qualified tax professional about your filing obligations.

Before the season opens

1. Tell your contractors Wingspan will email them. Contractors are more likely to open a tax email from a company they've heard of. Send the pre-Wingspan email in Contractor experience before Wingspan's outreach starts.
2. Publish a contractor help article. Start from the contractor FAQ template and replace the placeholders with your company name and your 1099 support email.
3. Decide who supports what. Wingspan support helps contractors who have a Wingspan account. Your team handles contractors who can't sign in, payment questions, and corrections. See Responsibilities and limitations.
4. Check what Wingspan doesn't file. Trusts, backup withholding, ITINs, non-zero withholding, and several other cases are out of scope. Read Responsibilities and limitations before you rely on Wingspan for every form.
5. Configure filing settings. Confirm your payer details and support contact, choose 1099-NEC or 1099-MISC (Box 6), and set calculation rules. See Set up 1099 filing.

Get your data complete

• Add every contractor who should get a form, including anyone you paid outside Wingspan. See Add contractors and off-platform payments.
• Import every off-platform payment. Itemized rows let contractors see exactly which payments are on their 1099.
• Supply W-9 data you already hold. If a contractor never confirms their details, Wingspan uses the W-9 information you provided. If neither of you provided it, the form can't be filed.
• Don't truncate data before you send it. Wingspan keeps full-length names and addresses and handles any shortening needed for PDFs or mail. See data length limits.
• Use legal first and last names for TIN matching. Wingspan sends only the first 70 characters of the name to TIN verification, and middle names can cause mismatches.

Watch year-end payment timing

Wingspan assigns a payment to a tax year using the date the payment is marked as paid (events.paidAt on the payable), not the date the work was done or the scheduled pay date.

A payroll approved on December 30 with a January 3 pay date can be marked paid on December 31 during processing, which puts it on the earlier year's 1099. If you need a payment to count in the new year, approve the payroll after January 1.

Instant Payouts don't move a payment between years: the amount counts in the tax year of the original scheduled payment. Off-platform payments and other non-standard flows can record the paid date differently. Contact support if you have questions about a specific payment type.

Check team permissions

Team members can only see contractors and payments in the sub-organizations they have access to. Someone missing access can see an incomplete total and file a wrong correction. Before the season, confirm that everyone who manages 1099s is assigned to every sub-organization they need. See Set up 1099 filing.

During filing

• Resolve every Action required form, or decide deliberately to exclude it. See 1099 statuses.
• Check payer information on the submit screen. If you file with incorrect payer information, the IRS requires you to mail a letter with the revisions.
• File by the recommended date in the season checklist so contractors receive forms before the IRS deadline.

After filing

• Watch for rejected forms. They return to Action required so you can fix and resubmit.
• Review contractor correction requests promptly. Corrections open after the IRS accepts your forms. See Correct tax forms.