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 19 guides in Strategies & advanced topics
Expert guide on qsbs exclusion: the $10m tax-free startup exit. Covers tax implications, strategies, IRS rules, and practical examples for tech employees and expats.
Expert guide on Section 1202 QSBS exclusion: the $10M tax-free startup exit strategy. Covers QSBS requirements, holding periods, exclusion percentages, and practical examples for tech employees and startup investors.
Tax-loss harvesting for shares acquired from RSUs or stock options: capital losses after vest or exercise, offsetting gains, $3,000 ordinary income net, IRC §1091 wash sales—not IRS Publication 525 RSU wage income at vest. Links to RSU tax guide and ESPP tools.
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.
Expert guide on calculating correct cost basis for RSUs, ISOs, NSOs, and ESPPs. Learn why your 1099-B is wrong, how to use Form 8949 adjustment codes, and how to fix already-filed returns to avoid paying tax twice on equity compensation income.
Simple guide to Form 1099-B when you have stock options or RSUs. Learn why the cost basis might be wrong, how to fix it, and avoid double taxation.
RSUs are not taxed twice on the same dollars when you track basis correctly. Learn vest vs sale taxation, W-2 income, stepped-up basis, sell-to-cover, and 1099-B mistakes that feel like double tax.
Step-by-step: map RSU vesting from Form W-2 to Form 1040, fix cost basis on Form 8949 and Schedule D, and avoid double taxation. For tech employees filing after RSU vesting.
Technical guide aligning IRS Publication 525 with RSU vesting, ordinary income taxation on Form W-2, supplemental withholding, and cost-basis reporting on Form 8949.
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.
Interactive RSU tax basis calculator and Form 8949 guide for tech employees: fix $0 broker cost basis using vest FMV already on Form W-2, report adjustments, and avoid paying tax twice on RSU sales.
Step-by-step guide to reconciling W-2 Box 1 wages with Form 1099-B cost basis adjustments on Form 8949 so you do not double-tax RSU vest income already reported under IRS Publication 525.
Step-by-step tax filing guide on correcting double-taxation on Form 1099-B using Form 8949 adjustments for RSU and ESPP equity compensation sales.
Step-by-step guide to adjusting your cost basis on Form 8949 to prevent double taxation on ESPP stock sales. Use Form 3922, the ESPP basis calculator, and adjustment code B.
How to calculate and report your adjusted cost basis for ESPP sales on Form 1099-B and Schedule D to avoid double taxation. Step-by-step Form 8949 guide paired with the ESPP Basis Adjustment calculator.
How to use IRS Publication 525 rules to adjust your RSU cost basis on Form 1099-B and avoid paying double tax on your vested shares.
Interactive calculator to prevent double taxation by adjusting the cost basis of vested RSUs reported on IRS Form 8949. Fix $0 broker basis using vest FMV already on Form W-2.
Step-by-step guide to correcting RSU and ISO cost basis on Form 8949 and Schedule D. Prevent IRS CP2000 notices, double taxation, and automated audit letters from 1099-B basis mismatches.
Step-by-step guide on correcting unadjusted cost basis on Form 1099-B for ESPP sales to avoid double taxation on Form 8949 and carry accurate gains to Schedule D.