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Stock tax guides

Clear, plain-English explanations of how U.S. stocks and equity compensation are taxed — each guide paired with a free calculator so you can put real numbers on your own situation.

How are stocks taxed? (start here)
The big picture: capital gains, dividends and equity comp, and how they fit together.
How are NSOs taxed?
Ordinary income at exercise, the withholding gap and your real cost basis.
The wash-sale rule
How the 30-day rule disallows a loss, and how to harvest losses safely.
Cost basis explained
What it is, FIFO vs specific-ID, and the $0-basis trap that double-taxes you.
W-8BEN & non-resident stock tax
30% dividend withholding, treaty rates, and why gains are usually not taxed.
Capital gains tax on stocks
Short- vs long-term rates, how the brackets work, and legal ways to pay less.
How are RSUs taxed?
Tax at vesting, the 22% withholding gap and the cost-basis double-tax trap.
How is ESPP taxed?
Qualifying vs disqualifying dispositions, the lookback and the discount tax.
AMT on stock options (ISOs)
Why exercising and holding ISOs can trigger the Alternative Minimum Tax.
RSU double taxation & the 8949 fix
Why the $0 cost basis double-taxes you, and exactly how to correct it.
ISO vs NSO
The tax differences between the two stock-option types, side by side.
Is an ESPP worth it?
When the discount beats the tax and concentration risk — and when it does not.
When to sell RSUs
Sell at vesting or hold? The tax and diversification math, decided.
How are dividends taxed?
Qualified vs ordinary dividends and the 0/15/20% rate on qualified ones.
Form 8949 & Schedule D
How to report stock sales and fix a wrong cost basis, line by line.
Tax-loss harvesting
Turn losers into tax savings without breaking the wash-sale rule.
ESPP qualifying disposition
The 2-year / 1-year holding tests and how much tax they save.
RSU withholding & the 22% gap
Why 22% is often too low and how to avoid an April surprise.