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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Comprehensive breakdown of how Portugal's IFICI (NHR 2.0) regime taxes foreign-sourced equity compensation, RSUs, and startup stock options for tech expats.
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.
Complete guide to the 3.8% Net Investment Income Tax (NIIT) on equity compensation. Learn which equity income triggers NIIT, how RSU sales, ISO dispositions, NSO exercises, and ESPP sales are treated, plus strategies to minimize the surtax.
Strategic guide to coordinating equity compensation with retirement accounts. Covers 401(k) maximization, Mega Backdoor Roth, IRA deductibility limits, Roth conversions, ESPP coordination, age-based strategies, and tax-bracket management for tech employees.
Expert guide on how forward and reverse stock splits and share buybacks affect RSUs, stock options, ESPPs, and your tax obligations. Covers anti-dilution adjustments, the 1% buyback excise tax, ISO $100K limit recalculations, and real-world examples from Apple, Google, Tesla, and Amazon.
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.
Compare RSUs (restricted stock units) with ESPP (employee stock purchase plan) and how people use 'ESOP' in job offers. Tax timing, discount vs free shares, $25k ESPP limit, and when to use an ESPP tax / total-return calculator.
Beyond taxes: choose ESPP contribution rates with cash-flow discipline, understand lookback economics, watch the $25k statutory limit, and align enrollment with liquidity and company blackout windows.
Decode Form W-2 Box 14 labels for RSUs, options, and ESPP: how they relate to Boxes 1 and 12, broker 1099-B basis, and common employer-specific codes.
Canadian ESPP taxation for tech employees: taxable employment benefits, T4 and RL-1 reporting, adjusted cost base, capital gains when you sell, CRA references, and worked CAD examples.
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.
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.