1099 Form Filing for Independent Contractors: A Complete 2026 Guide for Business Payers

Man reviewing paperwork. 1099 form

If your business pays freelancers, gig workers, or other nonemployees, you’re likely responsible for issuing 1099 forms each January. This guide explains what to file, when to file, and how to avoid common mistakes for the 2026 filing season (covering payments made in 2025). Who Needs to File and Why It Matters Businesses, nonprofits, trusts, … Read more

IRS AIR Production Cutover Schedule Released for TY 2025

air production cutover cartoon aca cutover

Today, the Internal Revenue Service (IRS) published the yearly AIR Production cutover schedule for the TY 2025. The temporary shutdown will impact all transmissions related to the Affordable Care Act (ACA), including corrections and replacements. AIR Production Cutover Schedule The shutdown for production will begin on Sunday, December 7, 2025 at 12am Eastern time. AIR … Read more

Important 2026 Deadlines for ACA, 1099, & W-2 Forms

2026 deadlines - mini white alarm clock

Staying ahead of the 2026 deadlines is essential for businesses preparing ACA, 1099, and W-2 filings. This guide highlights the key dates you need to know to stay compliant and avoid costly penalties while helping you plan, prepare, and file with confidence. Basic Information At the end of each year, employers must be sure they … Read more

What is Form W-2G & When to File with the IRS

What Is Form W-2G and When Do You File With the IRS

IRS Form W-2G is used to report gambling winnings and any federal income tax withheld from those winnings. There are different reporting and withholding requirements depending on the type of gambling, the amount of the winnings, and the ratio of winnings to wager.  What is Form W-2G? Form W-2G, Certain Gambling Winnings, is used to … Read more

Understanding IRS ACA Penalty Letters and How to Respond in 2025

ACA Penalty Letters

An employer may receive an ACA penalty letter if their filing is late, missing or inaccurate. The Affordable Care Act (ACA) requires that certain employers file and furnish ACA forms annually. If they do not meet these requirements, then the IRS may send out a notice to explain what went wrong and what to do … Read more

Line 8 Codes for Form 1095-B: A Clear Guide

Form 1095-B Line 8 Codes Explained

Form 1095-B, Line 8 Codes identify the origin of health coverage using a single letter. This helps the IRS understand where the policy came from and how the rest of the form should be interpreted. Form 1095-B is used to report which individuals are enrolled in minimum essential coverage and is typically filed by health … Read more

ACA of Boston: 1 Affordable Care Act Guide

ACA of Boston Affordable Care Act

When people search for “ACA of Boston,” they often come across two very different things: This article focuses on the Affordable Care Act and Massachusetts-specific healthcare rules that impact Boston employers, employees, and residents. Because Massachusetts had healthcare reform in place even before the federal ACA passed in 2010, the local requirements here are unique. … Read more

Affordable Care Act Reporting Tool – 4 Easy Steps!

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When the IRS made reporting Affordable Care Act (ACA) a requirement back in 2015, it made employer reporting an obligation. There are two form types that can be submitted: Form 1095-B Health Coverage & Form 1095-C Employer-Provided Health Insurance Offer and Coverage. Failure to fulfill the filing and furnishing obligations with the IRS results in … Read more

Electronic Form Delivery Simplifies IRS 1095, 1099, & W-2

Electronic Form Delivery

The IRS authorizes businesses to furnish electronic copies of certain tax forms, instead of a paper copy. Electronic Form Delivery Benefits There are many benefits to E-Delivery: However, electronic form delivery isn’t as simple as just sending forms via email; there are extensive rules and requirements for it. Electronic Form Delivery Requirements The requirements for … Read more

IRS AIR Production Cutover Schedule Released for TY 2024

IRS AIR Production Cutover Schedule Released for TY 2022 - Orange cone in parking lot

Today, the Internal Revenue Service (IRS) published the yearly AIR Production cutover schedule for the TY 2024. The temporary shutdown will impact all transmissions related to the Affordable Care Act (ACA), including corrections and replacements. AIR Production Cutover Schedule The shutdown for production will begin on Sunday, December 8, 2024 at 5pm Eastern time. AIR … Read more

2025 Deadlines for ACA, 1099 & W-2 Forms – IRS TY2024

2023 Deadlines, 2024 Deadlines, 2025 Deadlines, 2026 Deadlines - Image of Red Alarm Clock

Tax Year 2024 is coming to a close, which means that the filing season of 2025 is upon us! We’ve created this guide, so you don’t miss the 2025 deadlines. Basic Information When each tax year, or calendar year, comes to a close, employers must ensure that they meet all IRS tax requirements regarding filing. … Read more

Verify TIN Information for Form 1095-B

TINCorrect, IRS, SSA, SSN, Social Security Numbers, TIN verification. EIN, EIN verification, verifying TIN information, verify TIN information

After determining the individuals who should receive or be reported on the Form 1095-B, it is important to verify their taxpayer identification number (TIN) information. Verify TINs Before Filing Failing to include a recipient’s TIN, or providing the wrong TIN, could result in your filing being rejected, requiring corrections, re-issuing recipient copies, and potential penalties … Read more

Vermont ACA Filing Requirements – TY 2024

Vermont ACA - vermont usa

Many states have adopted Individual Mandates. Vermont is one of these states. While there are currently no additional requirements for employers, there will be if federal ACA reporting requirements are eliminated. What are the deadlines for Vermont ACA filings? There are currently no additional Vermont ACA reporting requirements. Conclusion Employers must keep ACA state requirements … Read more

DC ACA Filing Requirements – TY 2024

DC ACA district of columbia DC - washington monument

DC ACA Filing The District of Columbia requires all District residents to have Minimum Essential Coverage for themselves and dependents or pay a tax penalty. The DC law also requires employers to submit an information return regarding Minimum Essential Coverage to the DC Office of Tax and Revenue. Continue reading to learn more about updates to … Read more

Massachusetts ACA Filing Requirements in 2025

massachusetts aca - boston harbor

Many states have adopted Individual Mandates. Massachusetts ACA filing is now required for certain employers and insurance providers. Massachusetts Individual Mandate For TY 2025, along with federal requirements, Massachusetts has state regulations that require MA residents to have health coverage that meet certain standards. At the federal level, the coverage is known as Minimum Essential … Read more

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