The 2026 Capital Gains Tax Checklist.
Stocks, options, equity compensation, and digital assets — on one checklist, because they land on one Schedule D. The same intake framework we run on paid engagements, written by a credentialed team of Enrolled Agents, CPA, and Attorney.
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Ten sections, in the order they should be worked.
Most costly capital-gains errors are made before anyone opens a tax form — in the scoping and the basis. So that is where the checklist starts.
1. Scope the year
Every brokerage account, equity-comp portal, exchange, wallet, and K-1 issuer. Missing one account is the most common cause of an amended return.
2. Gather the documents
The consolidated 1099 and its realized gain/loss supplement, 1099-DA, Forms 3921 and 3922, K-1 footnotes, prior-year carryover worksheets.
3. Holding period & character
Short vs long term, the 0/15/20% brackets, the 3.8% NIIT, collectibles, and which contracts fall under §1256 at 60/40.
4. Basis & lot selection
Specific identification done properly, FIFO by default, per-wallet basis for digital assets, and the equity-comp double-tax trap.
5. Wash sales
The 61-day window, why an IRA purchase kills the loss permanently, and reconciling adjustments across brokers that cannot see each other.
6. Digital assets
Swaps, bridges, staking, mining, airdrops, LP exits, NFTs — and the internal transfers that create phantom gains.
7. Losses & carryforwards
The $3,000 ordinary offset, indefinite carryforward with character preserved, worthless securities, and §1244.
8. Plan the rate
Sequencing across tax years, gifting appreciated stock, installment treatment, QSBS eligibility, and ISO/AMT modelling.
9. State treatment
Most states give no preferential rate. Residency, part-year allocation, and the states that examine a move closely.
Section ten covers payment and filing mechanics — estimated-tax safe harbours, the RSU withholding gap, Form 8949 and Schedule D, Form 6781, and the FBAR and Form 8938 questions that non-U.S. brokers and exchanges raise.
Go deeper on your asset class.
The checklist is the intake. These are the mechanics, in full.
Capital gains for stock & options investors
Holding periods, basis reporting, wash sales, §1256, options treatment, and harvesting — the full guide.
Read the guideRSUs, ISOs & NSOs
Equity compensation from grant to sale, including the AMT exposure on an ISO exercise and the basis error that double-taxes it.
Read the guideCrypto tax guide for U.S. investors
Digital assets end to end — classification, per-wallet basis, DeFi, and 1099-DA reconciliation.
Read the guideWorked the checklist and the numbers still do not tie?
That is usually the signal. Book fifteen minutes — we will tell you honestly whether this needs a credentialed professional or just better software.