Generally, you cannot group multiple transactions together on a single Form 1099-B. The IRS requires that each disposition (sale or exchange) of securities or other assets be reported on a separate Form 1099-B, regardless of how many transactions you have in a calendar year.
When Must You Report Each Transaction Separately?
- Broker or barter exchange transactions: Each disposition must be reported on a separate Form 1099-B, even if multiple securities are sold in a single transaction.
- Covered securities: You must report covered securities with short-term gain/loss and long-term gain/loss on separate forms.
- Noncovered securities: If you choose to check Box 5 (indicating you are not reporting basis), you may still report noncovered securities on a separate Form 1099-B.
- Digital assets: If the asset is a dual classification digital asset (cleared/settled on a limited access regulated network), you must file Form 1099-B, not Form 1099-DA.
Exceptions to Separate Reporting
- Regulated futures, foreign currency, or Section 1256 option contracts: These may be reported on an aggregate basis on a single Form 1099-B, but you may also choose to report them separately by type (e.g., digital vs. non-digital assets).
- Barter exchanges with corporate clients: Transactions involving corporate members may be reported on an aggregate basis.
- Acquisition of control or substantial change in capital structure: If you are reporting proceeds from such events, you may file one Form 1099-B for both Regulation sections 1.6045-1 and 1.6045-3, but only if you choose to combine them.
Important Notes for Taxpayers
- Form 1099-B is issued by brokers and barter exchanges to report proceeds from the sale or exchange of securities or other assets.
- If you receive multiple Forms 1099-B, you must report each transaction separately when filing your tax return using Schedule D and Form 8949.
- Online Taxes (OLT) software can guide you through adding Form 1099-B data during your tax filing process.
Source:
Form 1099-B (2025) - Proceeds From Broker and Barter Exchange Transactions
Disclaimer: Always verify details with the current IRS Form 1099-B instructions and your state’s Department of Revenue. For complex situations, consult a tax professional or CPA.