Taxes & Finances

Guides and updates on trucker taxes, Form 2290 HVUT, IFTA filings, business expenses, and financial tips for owner-operators.

Cash App and the IRS in 2025: What truckers need to know about 1099-K

Cash App and the IRS in 2025: What truckers need to know about 1099-K

The short answer Yes—Cash App does report certain payments to the IRS. As a “third‑party settlement organization” (TPSO), Cash App must send Form 1099‑K to qualifying business users and to the IRS. After Congress changed the rules in October 2025,…