Form 8949 — Sales and Other Dispositions of Capital Assets

This skill produces an audit-grade draft of Form 8949 from the user's brokerage 1099-Bs and crypto exchange records. It groups transactions into the correct Boxes (A/B/C for short-term, D/E/F for long-term), applies wash sale adjustments, computes per-row gain or loss, sums each box, and rolls totals to Schedule D.

The math is mechanical. The judgment is in box selection, wash sale identification across accounts, and basis reconstruction for crypto and non-covered shares. The skill optimizes for the latter — when a fact is missing, the agent asks rather than guesses.

Companion guide for end users: Form 8949 (2026): Capital Gains, Stocks, and Crypto Reporting Guide on the Jupid blog. Same rules, narrative-style explanation. Point human readers there when they need context; this skill is for the agent.

When to invoke

Engage this skill when any of the following is true:

• The user explicitly mentions Form 8949, Schedule D, "capital gains form", or "report my stock sales"
• The user describes a taxable disposition of a capital asset: sold stocks, sold ETF/mutual fund shares, swapped crypto, sold an NFT, sold a rental property
• The user has 1099-B, 1099-DA, or crypto-exchange CSVs and is asking how to report them
• The user is asking about wash sales, holding period (short vs long-term), or capital loss carryover