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.
Search the library, pick a topic, or tap a tag. Your filters appear in the URL so you can bookmark or share them.
Filtered results and the full catalog below. Use the search and tags at the top of the page to narrow the list.
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:
Press Enter to search. Matches title, description, and tags.
Popular tags
Showing 13 guides
Expert guide on filing IRS Section 83(b) elections as a non-US person. Includes 30-day deadline mechanics, TIN/ITIN procedures, AMT implications, and why FEIE won't save you.
ISO vs NSO compared for employees: ordinary income vs capital gains paths, supplemental withholding and payroll taxes on NSOs, AMT on ISO exercise, the ISO/NSO split under the $100K rule, and early-stage startup considerations. Links to calculators for NSO tax and ISO AMT.
Complete 2026 guide to Employee Stock Purchase Plan (ESPP) taxation. Learn how to maximize the 15% discount, achieve qualifying dispositions, avoid double taxation traps, and optimize your after-tax returns with the 2+1 holding rule.
Expert guide on Alternative Minimum Tax (AMT) planning for ISO stock options. Learn how to calculate your AMT crossover point, avoid the $200K+ tax trap on paper gains, recover AMT credits via Form 8801, and coordinate exercises with RSU/NSO to minimize exposure.
Expert guide on ISO qualifying vs disqualifying dispositions. Learn the 2-year and 1-year holding rules, tax implications of each, and when to sell for optimal tax treatment.
Decision framework for exercising ISO options: same-day sale vs hold. Compare tax outcomes, cash requirements, AMT risk, and when each strategy makes sense.
Complete guide to MFJ vs MFS filing decisions for couples with stock options, RSUs, and ESPPs. Covers AMT exemption optimization, income splitting, capital gains bracket management, community property rules, and specific scenarios where filing separately saves thousands.
Complete guide to the One Big Beautiful Bill Act's impact on equity compensation in 2026. Covers permanent AMT exemptions, expanded QSBS exclusions, SALT cap increases, estate tax exemption updates, and actionable planning strategies for ISO exercises, startup exits, and estate planning with stock options and RSUs.
Step-by-step guide to reporting equity compensation on your 2025 tax return. Covers Form 8949, Schedule D, cost basis corrections, W-2 codes, Forms 3921/3922, AMT Form 6251, and the most common filing mistakes for RSUs, ISOs, ESPPs, and NSOs.
Guide to TCJA sunset implications for equity compensation. Covers potential bracket reversion to 39.6%, estate tax exemption halving, AMT changes, and strategic planning for stock options, RSUs, and QSBS before future tax rate increases.
When valuations fall, new 409A FMV may drop—changing future option exercise prices and AMT exposure. Learn what resets do and do not change for ISOs, NSOs, RSUs, underwater options, and repricing risks.
How prior-year AMT becomes a credit, how Form 8801 works conceptually, why ISO exercises create credits, and how recovery interacts with future regular tax vs tentative minimum tax. Educational—not filing instructions.
How the One Big Beautiful Bill (2025) affects AMT, QSBS, capital gains, NIIT, and withholding for tech employees with ISOs, NSOs, RSUs, and ESPP. Practical planning notes and what to verify each tax year.