While the finance world often fixates on 1099s in January, a larger, more complex beast is waiting in the wings: Payroll Year-End.
For most businesses, payroll is “set it and forget it”—until December. Then, suddenly, you are faced with a minefield of fringe benefit adjustments, retirement plan limits, and strict IRS deadlines.
The stakes for W-2s are arguably higher than for 1099s. These forms determine your employees’ personal tax refunds. A mistake here doesn’t just annoy the IRS; it angers your workforce.
As we approach the 2026 filing season (for the Tax Year 2025), there are critical updates you need to know. From the “Weekend Rule” shifting the filing deadline to new, higher contribution limits for your 401(k) plans, here is your executive guide to surviving the payroll rush.
The “Other” January Rush: Critical Deadlines
Just like with 1099s, the standard “January 31st” deadline has a twist this year.
Because January 31, 2026, falls on a Saturday, the deadline for filing Form W-2 with the Social Security Administration (SSA) and furnishing copies to your employees moves to February 2, 2026.
Warning: Do not let this extra weekend make you complacent. The penalties for late filing are indexed for inflation and are now steeper than ever.
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Tier 1 (Up to 30 days late): $60 per return.
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Tier 2 (Through Aug 1): $130 per return.
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Tier 3 (After Aug 1): $340 per return.
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Intentional Disregard: $680+ per return.
If you have 50 employees and you simply “forget” to file until September, that is a $17,000 mistake.
The Year-End Payroll Audit: A 5-Step Checklist
Before you authorize your payroll provider to generate W-2s, run through this audit. Once a W-2 is filed, correcting it (Form W-2c) is a manual, expensive nightmare.
1. The “Constructive Receipt” Trap (Bonuses)
A common question we get: “I want to give my team a bonus for 2025 performance, but I’m low on cash. Can I cut the check on January 5th but date it December 31st so they get it on their 2025 W-2?”
The Answer: No. This violates the Doctrine of Constructive Receipt.
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If the employee receives the funds in 2026, it is 2026 income.
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It goes on the 2026 W-2.
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The company takes the deduction in 2026 (for cash-basis taxpayers).
If you want the bonus to count for 2025, the check must be in the employee’s hands (or direct deposited) on or before December 31, 2025.
2. S-Corp Shareholder Health Insurance
If you own an S-Corporation and own more than 2% of the stock, the IRS has very specific rules for your health insurance.
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The company must pay the premiums (or reimburse you).
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That amount must be included in Box 1 (Wages) of your W-2.
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It is subject to income tax withholding but exempt from FICA (Social Security/Medicare) taxes.
Critical Step: Ensure your payroll provider has marked these premiums as “S-Corp Owner Health Insurance” before the final run. If you miss this, you risk losing the self-employed health insurance deduction on your personal 1040.
3. Personal Use of Company Cars
Do your sales reps drive company vehicles? Did they drive them for personal errands or commuting? That personal usage is a taxable fringe benefit. You must calculate the value of that personal use (using the “Lease Value Rule” or “Cents-Per-Mile” method) and add it to their W-2 income. This is often the #1 audit trigger for small fleets.
4. Verify Social Security Numbers (SSN)
Using a nickname or a typo in an SSN will trigger a mismatch letter from the SSA. Pro Tip: Use the Social Security Administration’s Social Security Number Verification Service (SSNVS) to batch-check your employee list before January 15th.
5. Review “De Minimis” Benefits
Did you give out $500 gift cards for the holidays? That is not a de minimis benefit. Cash (and cash equivalents like gift cards) are always taxable wages, regardless of the amount. You must add the value of those gift cards to your payroll so taxes can be withheld.
New Limits for a New Year (2026 Projections)
As you configure your payroll software for the first run of January 2026, you need to update your deduction limits. The IRS has announced increases due to inflation.
401(k) & 403(b) Limits
Retirement savers get a boost this year.
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Employee Deferral Limit: Increases to $24,500 (up from $23,500).
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Catch-Up Contribution (Age 50+): Increases to $8,000.
Social Security Wage Base
For high earners, the Social Security tax (6.2%) stops once they hit a certain income ceiling.
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2026 Wage Base: Increases to $184,500 (up from $176,100).
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Action Item: Ensure your payroll software is updated so you don’t stop withholding too early.
Health Savings Accounts (HSA)
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Self-Only Coverage: $4,400
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Family Coverage: $8,750
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Action Item: If employees have set “flat dollar” deductions for their HSAs, remind them to increase their contributions to take advantage of the new cap.
Decoding W-2 Box 12: The Most Confusing Box
Box 12 is where you report specific codes for various benefits. Using the wrong code is a fast track to an IRS notice. Here are the most common ones for small businesses:
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Code D: 401(k) Elective Deferrals. (The most common code).
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Code W: Employer AND Employee contributions to an HSA. (Yes, you must report both combined).
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Code DD: Cost of Employer-Sponsored Health Coverage.
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Code V: Income from the exercise of non-statutory stock options.
How Out of the Box Technology Simplifies Payroll
Payroll isn’t just about cutting checks; it’s about compliance, tax filings, and integrating with your accounting data.
If your current payroll process involves manual spreadsheets or disconnected systems, you are risking errors.
At Out of the Box Technology, we offer comprehensive payroll solutions that integrate seamlessly with QuickBooks.
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Automated Tax Filings: We handle the federal, state, and local filings so you never miss a deadline.
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Year-End Adjustments: We manage the S-Corp health insurance and fringe benefit add-backs for you.
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W-2 Distribution: We furnish digital and physical W-2s to your team, keeping you compliant with the February 2nd deadline.
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QuickBooks Integration: Your payroll journals map perfectly to your General Ledger, automating your job costing and expense tracking.
Don’t let the “Weekend Rule” catch you off guard. Let us handle the heavy lifting.
[CTA: Get Your Payroll Audit Today]
Frequently Asked Questions (FAQ)
What is the W-2 filing deadline for 2026? For the 2025 tax year, W-2s must be filed with the SSA and furnished to employees by February 2, 2026. The usual January 31st deadline falls on a Saturday, so it shifts to the next business day.
Are holiday gift cards taxable for employees? Yes. The IRS considers gift cards to be “cash equivalents.” They are always taxable wages and must be reported on the W-2, regardless of the amount (even a $25 card). Tangible gifts like a turkey or a gift basket are generally tax-exempt de minimis benefits.
How do I report health insurance for S-Corp owners? For shareholders owning more than 2% of an S-Corp, health insurance premiums paid by the company must be included in Box 1 (Wages) of the W-2. They are subject to income tax withholding but exempt from Social Security and Medicare taxes.
What is the 2026 401(k) contribution limit? For 2026, employees can contribute up to $24,500 to their 401(k). Those aged 50 and older can contribute an additional $8,000 catch-up contribution.
Can I handwrite W-2s for my employees? Technically yes, but it is highly discouraged. Handwritten forms are prone to processing errors. Additionally, if you have 10 or more information returns (W-2s and 1099s combined), you are required to e-file.
Conclusion: Start the Year Clean
A clean W-2 run is the best gift you can give your employees (and yourself) to start the new year. It sets the tone for a smooth tax season and keeps your business off the IRS penalty radar.
Take the time now—before the holidays—to audit your fringe benefits, verify SSNs, and update your deduction limits for 2026.
If you are unsure about S-Corp add-backs or constructive receipt rules, reach out to the experts at Out of the Box Technology. We ensure your payroll is precise, compliant, and stress-free.
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