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Reporting & forms
RSUs
How RSUs are taxed
RSUs are taxed as ordinary income the day they vest, then as capital gains on anything they earn after that. The trap is the gap between what your employer withholds and what you actually owe, and on a big year it pulls in surtaxes and quarterly payments too.
The RSU tax traps that hit in April, and how to dodge them
The flat rate your company withholds at vesting is almost always lower than what you owe, and that gap is just the first of the RSU traps. This is the complete field guide: the withholding gap, estimated taxes, the double-taxed 1099-B, short-term gains, blackouts, wash sales, acceleration, and the private-company bill on shares you cannot sell.
RSU tax estimator
A simple way to estimate the tax on a vesting year and the shortfall your withholding leaves behind. The interactive version is on the way.
Case study: the $14,000 double-tax RSU mistake
How a wrong 1099-B basis overcharged one filer, and how the amended return fixed it.
Restricted stock
ISOs
NSOs
NSO traps: the double-counted basis, the cash bills, and the deadlines that kill grants
The expensive NSO mistakes are quiet ones. The double-counted 1099-B basis taxes you twice, under-withholding ambushes you in April, illiquid stock owes cash you can't raise, and two deadlines erase winning options. Here is all of it.
Case study: an advisor's NSOs taxed on a 1099
No employer withholding meant the entire tax bill on the spread came due at filing, with nothing set aside.
ESPPs
The ESPP mistakes that quietly cost you money
From selling a few days early to paying tax twice on your discount, the ESPP punishes small oversights. Here is the full list of the traps and how to dodge each one.
ESPP taxes: qualifying vs disqualifying dispositions, the complete guide
How long you hold ESPP shares changes how the discount is taxed, splitting your gain between salary rates and the lower capital-gains rate. This is the whole story: the two clocks, the two formulas, the basis trap that taxes you twice, and the state and AMT wrinkles most people miss.
Case study: catching the ESPP double-tax before filing
One filer almost paid tax twice on the same discount. The fix was one number on one form, and it saved him about $4,000.
ESPP cost basis adjustment calculator
Work out your corrected basis so you do not pay tax on the discount twice.