Technical deep-dives on equity compensation taxation
Our comprehensive guides cover every aspect of stock options taxation, including RSU (Restricted Stock Units), ISO (Incentive Stock Options), NSO (Non-Qualified Stock Options), ESPP (Employee Stock Purchase Plans), 83(b) elections, and international tax planning strategies for tech professionals with equity compensation.
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Equity compensation is a significant part of total compensation for tech professionals, but the tax implications can be complex. Our guides cover the essential topics including:
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Showing 13 guides in Strategies & advanced topics
IRS Publication 525 and restricted stock units (RSUs): how vesting is taxed as wages, FMV at vest, W-2 reporting, supplemental withholding (often 22%), and why 83(b) usually does not apply to classic RSUs. Double-trigger RSUs and capital gains after vest.
Section 83(b) election for restricted stock and early-exercised options: must file within 30 days of transfer, official IRS Form 15620, Treasury Regulation §1.83-2, what Pub. 525 covers, and why 83(b) does not apply to typical RSUs.
Expert guide on donating equity shares to charity for tax benefits. Covers FMV deduction, AGI limits, qualified charities, donor-advised funds, and strategies to avoid capital gains tax while maximizing deductions.
Complete tax guide for Web3 and crypto employees receiving token compensation. Covers IRS treatment of tokens vs equity, taxation at receipt, vesting via smart contracts, staking rewards, airdrops, and regulatory ambiguity. Tokens are NOT stock options—fundamentally different legal and tax treatment.
Complete guide to the ISO $100,000 annual limit under IRC 422(d). Learn how options exceeding the limit are bifurcated into ISO and NSO, FMV at grant date, vesting order rules, and strategies to maximize tax benefits.
Complete guide to Section 83(i) tax deferral for private company stock options and RSUs. Covers the 80% employee grant requirement, 5-year deferral, eligibility, excluded employees, and why few companies offer it.
Step-by-step guide to filing a timely Section 83(b) election with the IRS: 30-day rule, what to send, sample language, copies for your employer, and common filing mistakes for restricted stock and early exercise.
If a company’s Section 409A valuation is challenged or defective, option strike prices may be off—triggering immediate income inclusion, penalties, and bad tax outcomes. Learn IRS Section 409A penalties, correction programs, and how employees get caught in the middle.
Technical guide to the ISO $100,000 annual limitation under IRC 422(d) and Treasury Regulation §1.422-4: first-exercisable shares, grant-date FMV, ordering rules, and automatic NSO conversion—plus links to calculators.
US citizens and green card holders living in Canada: how RSUs and options are taxed in Canada, worldwide US reporting, Form 1116 foreign tax credits, FBAR and Form 8938, and reconciling T4, RL-1, and any US payroll forms.
For tech employees with RSUs, this guide translates IRS Publication 525 into actionable advice on how vesting is taxed as wages and reported on a W-2.
Practical filing walkthrough for vested RSU shares: reconcile Form 1099-B with W-2 wage basis, pick the right Form 8949 box, use adjustment codes, compute holding period from acquisition, and carry totals to Schedule D without double taxation.
Step-by-step orientation to IRS Form 6251 for incentive stock options: where the ISO bargain element lands, how Form 3921 feeds the calculation, how Tentative Minimum Tax stacks against regular tax, and how Form 8801 tracks prior-year AMT credits without substituting for personalized advice.