LLCs and 1099s — Updated for 2026

The rush of April 15 is over, but for many tax professionals, the real headache has just begun: reconciling the mess of 1099s found during tax season. This session, led by 'The 1099 Guy' Jason Dinesen, dives into the complex world of LLCs and the ever-changing landscape of the One Big Beautiful Bill Act (OBBBA). We will address the 'Disregarded Entity' trap, the retroactive threshold changes for 1099-K (PayPal/Venmo), and the new 2026 e-filing mandates. This isn't just a 'how-to'—it’s a 'how-to-fix' session designed for the post-deadline cleanup.

We will dive deep into why "Disregarded Entities" cause the most 1099 errors, how to handle the retroactive threshold changes for payment apps, and the mandatory 2026 e-filing requirements. If you found errors on your clients' books this tax season, this is your roadmap to fixing them before the IRS sends a notice.

Learning Objectives:

Identify the correct reporting name and TIN for various LLC structures (Single Member vs. Multi-Member).
Navigate the 1099-K 'Payment App' confusion: Reconciling personal vs. business transactions under the $20,000 OBBBA threshold.
Execute the new 2026 E-filing requirements and understand the IRIS portal mandates.
Apply penalty mitigation strategies for late or corrected 1099s discovered after the April 15 individual deadline.

Session Highlights:

The LLC Trap: Why an EIN on a W-9 is often the wrong number to use for a single-member LLC.
Payment App Reality Check: Sorting through the mess of Venmo, PayPal, and Zelle payments under the $20,000 OBBBA rules.
E-Filing for Everyone: The "10-form" threshold is here—why almost every business is now legally required to e-file in 2026.
The "One Big Beautiful Bill Act" (OBBBA): A plain-English breakdown of how this 2025/2026 law changed your workflow.
Backup Withholding: The 24% rule you can’t afford to ignore when a contractor refuses to provide a TIN.

Who Should Attend

CPAs & Enrolled Agents: Looking to resolve issues found during the 2025/2026 filing season.
Bookkeepers: Who manage vendor payments and W-9 collection throughout the year.
Small Business Owners: Who paid contractors via apps and are worried about upcoming IRS audits.
Tax Managers: Needing a 2026 compliance update on the OBBBA's impact on information returns.

Credits and Other information :

IRS CPE Credits: 2.0 TAX

Location: Virtual/Online

Delivery method: Group Internet Based

IRS Course ID: DFFSC

Attendance Requirement: Yes

Session Duration: 2 Hours

Case Studies and Live Q&A session with speaker

PowerPoint presentation for reference

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