W-2 and 1099-NEC Filing: What US Employers Need to Know
Year-end tax filing is one of the highest-stakes compliance tasks for any US employer. Miss a deadline or file incorrectly and you face IRS penalties. Here's everything you need to stay compliant.
Key Deadlines
| Form | Recipient Deadline | IRS Filing Deadline |
|---|
|------|--------------------|---------------------|
| W-2 | January 31 | January 31 (paper & e-file) |
|---|---|---|
| 1099-MISC | January 31 | February 28 (paper) / March 31 (e-file) |
Important: If January 31 falls on a weekend, the deadline moves to the next business day.
W-2 Filing Checklist
- Collect all employee SSNs — verify against your payroll records
- Confirm year-to-date wages and withholdings in your payroll system
- Account for pre-tax deductions (401k, HSA, FSA)
- Include employer-paid health insurance in Box 12 (Code DD)
- Reconcile total W-2 wages against quarterly 941 filings
- File Copy A with the SSA by January 31
- Distribute employee copies by January 31
- Keep Copy D for your records (4 years)
1099-NEC Filing Checklist
- Identify all contractors paid $600 or more during the year
- Collect completed W-9 forms for each contractor
- Verify contractor TINs against IRS TIN Matching before filing
- Confirm payments through all channels (check, ACH, wire)
- Note: Payments via PayPal/Venmo/credit card are reported by the payment processor — do NOT double-report
- File Copy A with the IRS by January 31
- Send contractor copies by January 31
Common Mistakes That Trigger IRS Penalties
- Wrong TIN/SSN — Always verify before filing, not after
- Missing 1099s for LLC vendors — LLCs taxed as sole proprietors or partnerships still require 1099s
- Forgetting state filing requirements — Many states have their own W-2/1099 deadlines and filing portals
- Late corrections — If you file an incorrect form, file a corrected version immediately. Penalties compound over time.
IRS Penalty Rates (2025)
| Days Late | Penalty per Form |
|---|
|-----------|-----------------|
| 1–30 days | $60 |
|---|---|
| After Aug 1 or not filed | $310 |
| Intentional disregard | $630 |
How OneSky Offshore Helps
Our team manages W-2 and 1099 preparation support as part of our payroll and tax services. We organize your data, reconcile your records, and prepare everything for review — so your CPA or tax preparer can file with confidence and you're not scrambling in January.
Contact us to learn how we handle year-end compliance for US clients.