In the second session of Greenshades' Year-End Power Series, our experts returned to guide payroll and HR teams through the complexities of filing season.
Kieran O’Connor (Director of Managed Services) and Josh McCullough (Chief Marketing Officer) delivered a session packed with essential dates, compliance rules, and best practices to help you file with confidence. From federal deadlines to state-level curveballs, this recap covers the key takeaways to keep you on track.
⚠️Note: This information is for informational purposes only and does not constitute formal tax, legal, or compliance advice. Always consult with qualified tax advisors, legal counsel, and your organization’s internal teams for guidance specific to your situation. Additional regulations may apply. For the most accurate and up-to-date information, refer to official government resources and regulatory agencies.
Table of Contents
Federal Filing Foundations: Dates, Forms & Deadlines
A successful year-end starts with knowing your deadlines. In 2026, many key filing dates fall on a weekend or holiday, pushing them to the next business day. It’s best to plan ahead and submit your forms early to avoid the last-minute rush.
Key adjusted deadlines for tax year 2025 include:
- February 2, 2026: W-2, various 1099s, 1098, 940
- February 17, 2026: 1099-B, 1099-S, 1099-MISC (with data in Box 8 or 10)
- March 16, 2026: 1042
Remember to check your vendor's submission cutoffs. Building in extra time ensures your forms are printed, mailed, and filed on schedule without any surprises.
The 10-Form E-File Rule: What It Means for You
So, does your business need to e-file this year? Odds are, the answer is yes.
The IRS and Social Security Administration (SSA) require businesses that file 10 or more aggregate information returns to e-file. This means you must count all federal return types combined. With this low threshold, nearly every employer is required to file electronically.
E-filing isn't just a requirement; it's a best practice. It provides instant confirmation of receipt and faster processing, reducing the risk of errors and delays.
Where & How to E-File
Different forms go to different agencies through different systems:
- SSA: W-2s are filed via Business Services Online (BSO).
- IRS: 1099s and other information returns are filed through the new Information Returns Intake System (IRIS), which is replacing the FIRE system.
- IRS: ACA forms (1094/1095) are submitted through the AIR System.
Filing directly with these agencies requires a Transmitter Control Code (TCC). However, using an approved transmitter like Greenshades handles this requirement for you, simplifying the entire process.
For more information about each of these portals and their requirements, check out the Greenshades blog: Is your organization required to e-file year-end forms (Spoiler: The odds are yes!)
Validating SSNs, EINs, and TINs
Accurate identification numbers are critical for avoiding rejections and penalties. Before you file, it’s essential to validate your employee, employer, and vendor data.
- Social Security Numbers (SSNs): Use the SSA’s verification service (SSNVS) to confirm employee names and numbers match. Look for common placeholder patterns (e.g., leading zeros, sequential numbers) and correct them early.
- Employer Identification Numbers (EINs): Ensure your EIN matches IRS records and is consistent across all payroll systems, W-2s, and 941s. This is especially important for multi-entity organizations.
- Taxpayer Identification Numbers (TINs): For 1099 reporting, use the IRS TIN Matching Program to confirm vendor information. If a TIN is missing or invalid, you must apply backup withholding at a rate of 24%.
Documenting your verification efforts is a crucial step. Save confirmation records from the SSA and IRS as part of your year-end files for future reference or potential audits.
State-Level Considerations: OBBBA, ACA, and PFML
Federal compliance is only half the battle. States often have their own unique filing requirements, and you should never assume federal rules apply everywhere.
OBBBA Provisions and Updates
Tax year 2025 is a transition period for the overtime and tip tax exemptions under the One Big Beautiful Bill Act (OBBBA). While W-2s will not include updated boxes for qualified overtime and tips this year, the IRS encourages employers to provide this information to employees through other means, such as a supplemental statement or by using Box 14.
State-level adoption of these provisions varies:
- Confirmed Decoupling: California, Colorado, and Rhode Island have confirmed that tips and overtime remain taxable for 2025.
- Partial or Pending Adoption: Massachusetts, North Carolina, and Pennsylvania are still reviewing or proposing changes.
- Presumed Coupling: States with "rolling conformity," like Oregon, are expected to align with federal rules unless they actively opt out.
Other State Considerations
- ACA Mandates: California, DC, Massachusetts, New Jersey, Rhode Island, and Vermont have their own ACA reporting requirements and submission portals.
- Unique W-2 Fields: Some states require additional data on W-2s, such as hours worked or Paid Family and Medical Leave (PFML) contributions.
- Combined Federal/State Filing (CF/SF): This program allows you to file 1099s with the IRS, which then forwards the data to participating states. However, not all states participate, so verify the current list and plan for direct state filings where necessary.
How Greenshades Keeps You on Track
Navigating year-end can be challenging, but you don't have to do it alone. The Greenshades Year-End Forms platform simplifies the entire process.
- Save Time: Import data directly from Greenshades Payroll, your ERP, or Excel.
- Streamline Processing: Manage W-2s, 1099s, and ACA forms in one secure solution.
- Easily Distribute: E-file directly with federal agencies, download e-filing submissions, or use our professional print-and-mail services.
Our platform is backed by a team of compliance experts who monitor legislative changes, so you can stay ahead of new regulations and file with confidence.
Q&A
(This section will be updated with questions and answers from the live session.)
