The rise of digital payment methods including credit cards, Venmo, PayPal, Cash App, and other third-party platforms has created widespread confusion around Form 1099 reporting responsibilities. Many organizations assume that paying a vendor automatically triggers a Form 1099-NEC or 1099-MISC requirement. However, when payments are made through certain channels, the reporting obligation may shift entirely under Form 1099-K rules.

This course provides a practical, real-world overview of Form 1099-K and its interaction with traditional 1099 reporting. Participants will learn how payment method not just the nature of the transaction determines reporting obligations, and why accounts payable teams often do not issue any form at all for certain payments. 

The session explores key concepts such as payment card transactions, third-party settlement organizations (TPSOs), and how platforms like Venmo, PayPal, and BILL can create different reporting outcomes depending on how payments are made. Attendees will also examine the evolving 1099-K reporting thresholds, including recent legislative changes and their practical implications for compliance.

Through examples and scenarios, the course highlights common pitfalls, including misclassification of payment types, incorrect issuance of Forms 1099-NEC, and misunderstandings about peer-to-peer payment platforms. The session also addresses related topics such as backup withholding responsibility, foreign vendor considerations, and how to interpret Form 1099-K when received.

Designed to be timely, relevant, and actionable, this course equips professionals with the knowledge needed to navigate the increasingly complex intersection of payment methods and information reporting requirements.

1. Introduction to Form 1099-K and Payment Reporting

      •     Background and purpose of Form 1099-K

      •     Relationship to Forms 1099-NEC and 1099-MISC

      •     Why payment method drives reporting outcomes

2. Payment Methods and Reporting Implications

      •     Credit and debit card payments

      •     Peer-to-peer platforms (Venmo, PayPal, Cash App)

      •     Payment platforms and hybrid systems (e.g., BILL)

      •     Determining when reporting responsibility shifts

3. Third-Party Settlement Organizations (TPSOs)

      •     Definition and characteristics of a TPSO

      •     Examples of TPSO vs. non-TPSO payment methods

      •     Identifying TPSO transactions within platforms

4. Applying the 1099-K “Tie-Breaker” Rules

      •     When 1099-K overrides 1099-NEC/MISC reporting

      •     “Goods and services” vs. personal payments

      •     Business vs. personal account distinctions

5. Reporting Thresholds and Legislative Changes

      •     Historical thresholds under the ACA

      •     Changes under the American Rescue Plan Act

      •     Now, can to ACA after the One Big Beautiful Bill

6. Real-World Scenarios and Common Pitfalls

      •     Mixed payment methods across vendors

      •     Partial reporting situations

      •     Misunderstanding platform functionality

      •     Improper issuance of 1099-NEC

7. Additional Compliance Considerations

      •     Backup withholding responsibility

      •     Foreign vendor payments

      •     Why “just issuing a 1099 anyway” can be incorrect

8. Recipient-Side Considerations

      •     What to do when receiving a 1099-K

      •     Gross vs. net reporting issues

      •     Reconciling 1099-K amounts for tax reporting

After completing this course, participants will be able to:

• Identify when Form 1099-K reporting applies based on payment method, including payment cards and third-party settlement organizations (TPSOs).
• Determine when an organization is not required to issue a Form 1099-NEC or 1099-MISC due to the application of 1099-K rules.
• Distinguish between TPSO and non-TPSO transactions, including how different payment platforms impact reporting obligations.
• Apply current 1099-K reporting thresholds and recent legislative changes to real-world payment scenarios.
• Recognize common compliance risks, including improper 1099 issuance and misunderstandings related to digital payment platforms.

• Accountants
• Bookkeepers
• Office Managers
• Human Resources Professionals
• Compliance Professionals
• Business Owners

During the Q&A session following the live event, ask a question and get a direct response from our expert speaker.

Important Notice for Our “Live” Attendees: If you have enrolled in the “Live Webinar,” you will get your instruction kit before 24 hours of the live class.

For Recorded and E-transcript Participants: If you have signed up for the “Recorded” class or for the “E-transcript,” you will get access to the “Recording link” or the “PDF” within 24-48 hours of the live class.

SPEAKER

Jason Dinesen, LPA, EA

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Jason Dinesen is the President of Dinesen Tax & Accounting, P.C., a public accounting firm in Indianola, Iowa. His practice focuses on accounting and bookkeeping services, tax preparation and business advising to individuals with a business focus ranging from home-based businesses to multistate corporations and not-for-profits. Dinesen has extensive experience working with a third-party administrator of retirement plans and is a prior presenter of multiple 1099 seminars. Dinesen majored in corporate communications with a minor in management from Simpson College.

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