The 1099 Deep Dive: Webinar Recap

In this latest installment of the Greenshades Year-End Power Sessions, we zeroed in on one of the most complex areas of year-end reporting: the 1099 series.

Led by Kieran O’Connor (Director of Managed Services) and hosted by Mandy Haberkamp (Director of Demand Generation), this session was packed with regulatory updates, practical breakdowns, and compliance best practices to help you tackle 1099s with confidence.

⚠️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.  

You can watch the full session here:

Table of Contents:

• Key Takeaways
• 1099 Filing Breakdown
• TIN and EIN Validation
• OBBBA: Reporting Relief in 2025
• Other 1099 Forms You May Encounter
• Combined Federal/State Filing (CF/SF)
• Filing & Timing: Federal Deadlines
• Avoiding Common Errors
• Requesting Extensions
• Filing Corrections
• Session Q&A

Key Takeaways

There’s more to 1099 reporting than just selecting the right form — especially in light of 2025’s updated rules and shifting thresholds. Here are the biggest takeaways from the session:

The 1099-K Threshold Is Reinstated

Recent legislation reversed a proposed change, bringing the threshold back to its original standard.

• The One Big Beautiful Bill Act (OBBBA) reinstated the prior threshold of $20,000 and 200 transactions for 1099-K reporting.

Golden Parachute Payments Have a New Home

Updates to form structure mean these payments now appear on a different form than in previous years.

• Box 14 on the 1099-MISC has been reserved for future use.
• Excess golden parachute payments are now reported in Box 3 on the 1099-NEC.

$600 Threshold Still Applies for NEC (For Now)

This familiar threshold isn’t changing just yet—but expect an update soon.

• In 2025, you must still issue Form 1099-NEC for services totaling $600+.
• This threshold is projected to increase to $2,000 in tax year 2026.

Mandatory E-Filing Rules Tightened

Even small organizations may now be required to e-file.

• If you're filing 10 or more combined information returns, e-filing is required.
• While FIRE is still available through 2026, IRIS will become the long-term standard for submitting forms electronically.

1099 Filing Breakdown

The session broke down the three most common 1099 forms and when each should be used.

1099-MISC

Used for miscellaneous payments not related to services, this form is a catch-all for several income types.

• Issue for $10+ in royalties or $600+ in rent, prizes, medical payments, and other non-service income.
• In 2025, Box 14 is no longer used. Golden parachute payments have moved to the NEC form.

1099-NEC

Designed for service-based payments, this is the go-to form for nonemployees and freelancers.

• Issue if you paid $600+ directly (via cash, check, ACH) for services to independent contractors, consultants, or attorneys.
• For 2025, Box 3 is newly designated for excess golden parachute payments.
• Payments routed through platforms like PayPal don’t belong here (see 1099-K instead).

1099-K

This form is issued by payment platforms—not employers—for qualifying transactions.

• Used for payments processed through third-party apps (e.g., Stripe, DoorDash).
• Applies if the recipient earned $20,000+ across 200+ transactions.
• Employers do not issue this form—the platform

Clarifying NEC vs. K

Understanding who should issue which form—and when—is essential to avoid duplicate reporting.

• If you paid the worker directly, file a 1099-NEC.
• If the payment was processed by a TPSO, they file the 1099-K, not you.

Deep Dive into 1099 Logistics

TIN and EIN Validation

Accurate tax identification data is foundational to successful filing.

• Use the IRS TIN Matching Service to confirm contractor information before issuing 1099s.
• Validate EINs across systems—especially in multi-entity environments—to ensure consistency.
• Look for placeholder or suspicious numbers (e.g., all 9s or sequential digits) and correct them early.
• Greenshades clients can run validations from within the platform prior to filing deadlines.

OBBBA: Reporting Relief in 2025

New rules under OBBBA introduce reporting for tips and qualified overtime, but 2025 is a transition year.

• The IRS is not requiring separate boxes on 1099s or W-2s in 2025 for tips or qualified OT.
• Employers will not be penalized if the base form is complete and correct.
• Workers can still calculate and report these items using supplemental documentation.

Contractors still need visibility into their year-end earnings, even if not itemized on tax forms.

• Provide detailed earnings statements, receipts, or reports that break out tips and bonuses.
• Use POS reports or transaction dashboards to help contractors identify deductible income.
• This ensures compliance while helping workers claim their tax credits accurately.

Other 1099 Forms You May Encounter

While the NEC, MISC, and K forms are most common, others may apply depending on your industry.

• Examples include 1099-B, 1099-C, 1099-DIV, 1099-INT, 1099-PATR, 1099-R, and 1099-S.
• The IRS 1099 series includes 20+ different forms, each with unique rules and thresholds.

Combined Federal/State Filing (CF/SF)

The CF/SF program simplifies multi-jurisdiction reporting, but participation varies.

• When enabled, IRS forwards 1099 data to participating states.
• Confirm which states participate—some, like California and Pennsylvania, require direct filing.
• Greenshades supports CF/SF and helps you stay compliant with state-by-state requirements.

Filing & Timing: Federal Deadlines

Key federal dates for tax year 2025 to keep in mind:

• February 2, 2026: Most 1099s due to recipients and IRS (NEC, MISC, DIV, K, R, etc.)
• February 17, 2026: 1099-MISC with Box 8/10 and real estate-related 1099s
• March 31, 2026: Deadline to e-file remaining 1099s with the IRS
  
  

Avoiding Common Errors

These issues continue to cause IRS rejections year after year.

• Misclassifying forms: NEC vs. MISC vs. K
• Invalid or missing TINs
• Incorrect reporting method (e.g., direct vs. platform payment)
• State allocation mistakes
• Attorney reporting errors, including the wrong form for legal fees or proceeds
• Filing on paper when e-filing is required (if 10+ forms)

Requesting Extensions

If you need more time, follow the IRS rules closely.

• Use Form 15397 to extend time to furnish recipient copies.
• Use Form 8809 to extend time for filing with the IRS.
• Extensions are not automatic and should be submitted early.

Filing Corrections

Corrections must follow the method of your original submission.

• FIRE corrections follow Pub 1220
• IRIS Portal (CSV) corrections follow Pub 5717
• IRIS A2A corrections follow Pub 5718
• Best practices: Correct quickly, never resend entire files, and keep detailed records.

Session Q&A

How Greenshades Can Help

Whether you’re managing 50 forms or 5,000, the Greenshades Year-End Forms platform helps you streamline the process from prep to print.

• Save Time: Import data from Greenshades Payroll, your ERP, or Excel templates.
• Streamline Processing: Manage W-2s, 1099s, 1095s, and more in one place.
• Distribute with Ease: E-file with federal agencies, download submissions, or use our print & mail services.

Plus, Greenshades is an IRS-approved transmitter, which means you don’t need your own TCC—we handle it for you.