Every year, USVI employers scramble in January trying to reconcile records, track down missing information, and rush through W-2 and 1099 deadlines. It doesn’t have to work that way. Year-end payroll is completely predictable. Every deadline, every form, every reconciliation step happens on the same schedule every year. The businesses that sail through January start in November.
Download the checklist here: Lasinja Year-End Countdown Checklist
Key Year-End Payroll Deadlines
| Deadline | What’s Due |
|---|---|
| January 31 | W-2s to employees; 941VI Q4 filed; 1099-NECs to contractors |
| February 28 | Paper W-3 and W-2 copies filed with SSA (if not e-filing) |
| February 28 | Paper 1099s filed with IRS |
| March 31 | Electronic W-2/W-3 filing with SSA |
| March 31 | Electronic 1099 filing with IRS |
The 30-Day Countdown
December 1–7: Audit Your Year-End Payroll Records
- Pull your YTD payroll register and verify total gross wages for every employee
- Confirm all pay periods for the year have been processed — no missing runs
- Check that terminated employees are still in the system with correct final pay dates
- Verify all bonus and commission payments are captured and correctly classified
- Confirm that VIESA withholding has been applied consistently throughout the year
December 8–14: Reconcile Against Your 941VI Filings
This is the step most employers skip, and it’s the one that causes W-2 correction headaches in February. Your four quarterly 941VI filings should add up to your annual payroll totals. Check these specifically:
- Total wages on W-3 must match total wages across all four 941VIs
- Total VI income tax withheld on W-3 must match the sum of Line 3 across all four quarters
- Total Social Security and Medicare wages must reconcile with Lines 5a–5c across all quarters
- If you find discrepancies, file an amended 941VI now — before W-2s go out
December 15–21: Verify Employee Information
- Confirm every employee’s legal name matches their Social Security card exactly. SSA rejects W-2s with name/SSN mismatches.
- Verify all Social Security numbers are correct
- Confirm current mailing addresses for employees receiving paper W-2s
- Check that employees who moved during the year have updated their address
- Make sure new hires from the second half of the year have complete records
December 22–28: Contractor Sweep
- Pull all contractor payments — anyone paid $600 or more needs a 1099-NEC
- Confirm you have a completed W-9 on file for every contractor
- Note any contractors paid as corporations — they generally don’t require a 1099 except for legal or medical services
December 29–31: Final Pay Period
- Process your final pay period of the year and confirm the date falls within the calendar year
- Don’t advance any January pay periods into December for convenience — it creates year-end complications
- Confirm your Q4 941VI figures are accurate before the January 31 deadline
- Make your final 501VI deposit for Q4 taxes
January 1–15: Generate and Review W-2s and 1099s
- Generate all W-2s and do a final review before distribution — check Box 1 (wages), Box 2 (federal withholding), Box 16 (VI wages), and Box 17 (VI tax withheld)
- Verify VIESA withheld is reflected in the appropriate box
- Generate 1099-NECs for all qualifying contractors
- Cross-reference W-3 totals against your reconciled 941VI YTD one more time
January 16–31: Distribute and File
- Distribute W-2s to all employees by January 31
- Distribute 1099-NECs to contractors by January 31
- File Q4 941VI by January 31
- File 1099-NECs with the IRS by January 31
- Begin W-3 and SSA filing preparation (due February 28 paper / March 31 electronic)
The Most Common W-2/941VI Mismatches
The BIR and SSA cross-reference your W-3/W-2 totals against your quarterly 941VI filings. These mismatches trigger notices most often:
- Mid-year bonuses processed separately from regular payroll and missed on the 941VI
- Termination pay recorded in a different quarter than when it was actually paid
- VIESA discrepancies — withheld all year but not accurately reflected on the W-2
- Name/SSN mismatches — SSA rejects the W-2 and sends a notice back to you
- Rounding errors accumulated across four quarters producing a W-3 total that’s a few dollars off
How Lasinja Makes Year-End Payroll Simple
Because Lasinja tracks every payroll run, every tax withholding, and every VIESA deduction in real time, your year-end numbers are always ready. W-2s are generated automatically from your payroll data. Your 941VI quarterly totals already reconcile with your annual W-3 figures because they come from the same source.
What used to take two weeks of prep work takes a few hours.
Sign up for Lasinja today and close the books with confidence.
Download the checklist here: Lasinja Year-End Countdown Checklist
For a full quarterly filing walkthrough, see Form 941VI Explained. For all 2026 deadlines in one place, the 2026 USVI Payroll Compliance Calendar has you covered.