Tax Guides
Plain-English explanations of tax topics that move the needle for AlwaysOnTax users. Written by the team at AlwaysOnTax — read, then run your own numbers in the app.
Equity Compensation
Employee Stock Purchase Plans (ESPPs): A Tax Guide
How ESPPs work, how the discount and look-back features compound, and the tax difference between qualifying and disqualifying dispositions.
Equity holdersIPOs & Acquisitions: What Happens to Your Equity
What happens to your ISOs, RSUs, NSOs, and ESPP shares when your company goes public or gets acquired — lockups, tax timing, and AMT considerations.
Equity holdersIncentive Stock Options (ISOs): A Guide to Timing and Tax Strategy
How ISOs are taxed, when AMT kicks in, and how to plan exercises across multiple years. A plain-English guide for employees with equity compensation.
Equity holdersNonqualified Stock Options (NSOs): A Tax Guide
How NSOs are taxed at exercise and at sale, why they differ from ISOs, and the cost-basis trap that can lead to double taxation.
Equity holdersRestricted Stock Units: Understanding Vesting, Taxation, and Strategy
How RSUs are taxed at vesting, how withholding works, and what to expect at sale. A plain-English guide for employees with equity compensation.
Equity holdersThe $100,000 ISO Limit: Understanding the Rule and Planning Across Years
The $100K ISO rule caps how many options can become exercisable in a year. Learn how cliff vesting and overlapping grants can trigger NSO conversion.
Capital Gains & Losses
Understanding the Net Investment Income Tax (NIIT)
How the 3.8% Net Investment Income Tax works — who owes it, what counts as investment income, and how to reduce your exposure.
InvestorsTax-Loss Harvesting: Turning Investment Losses into Tax Savings
How to use realized investment losses to offset capital gains and reduce your tax bill. Mechanics, wash sale considerations, and when it pays.
InvestorsThe Wash Sale Rule: When You Cannot Claim a Capital Loss
How the wash sale rule disallows capital losses when you re-buy a substantially identical security within a 61-day window. What counts, what doesn't, and how to comply.
Real Estate
Tax Planning for Home Purchases
How buying a home changes your tax picture — mortgage interest deduction, property taxes, the SALT cap, points, and the itemization flip.
LandlordsRental Property Tax Basics
How rental income, expenses, and depreciation work on Schedule E. Passive activity loss rules, the $25K allowance, and depreciation recapture at sale.
HomeownersSelling Your Home: The Section 121 Exclusion
How the Section 121 home sale exclusion shelters up to $250K (single) or $500K (MFJ) of gain on selling a primary residence. Tests, traps, and planning.
Education
Advanced 529 Plan Strategies: Superfunding and Multi-Generational Planning
How to superfund a 529 with 5 years of contributions at once, change beneficiaries across family members, and roll unused funds into a Roth IRA.
ParentsEducation Tax Credits: AOTC and Lifetime Learning Credit
How the American Opportunity Credit (AOTC) and Lifetime Learning Credit work, who qualifies, and how to coordinate them with a 529 plan.
ParentsK-12 Tax Strategies: Using a 529 for Private School and Beyond
How the OBBBA's 2026 changes let families use 529 plans for K-12 expenses up to $20,000 per year — and the state tax caveats that may offset the benefit.
Students & familiesScholarships and Tax Treatment
When scholarships and stipends are tax-free, when they become taxable, and how intentional treatment can unlock a larger AOTC. A guide for students and parents.
BorrowersStudent Loan Interest Deduction
How to claim up to $2,500 of student loan interest as an above-the-line deduction. Eligibility, income phase-outs, and what counts as qualified interest.
ParentsTax-Efficient College Savings: 529 Plans and Strategic Planning
How 529 plans work, who should own them, and how the FAFSA's two-year lookback shapes college savings strategy. A guide for parents and grandparents.
Retirement Accounts
The Backdoor Roth IRA: How High Earners Contribute to Roth Accounts
How high earners can contribute to a Roth IRA via the backdoor — Traditional IRA → Roth conversion. The pro rata rule, common pitfalls, and how to fix them.
ParentsCustodial Roth IRAs for Minors: An Underused Retirement Tool
How a custodial Roth IRA lets a working minor start decades of tax-free compounding. Earned-income rules, 2026 limits, and who can fund the account.
High earnersUsing an HSA as a Supplementary Retirement Account
How high earners can turn their HSA into a stealth retirement account by paying medical expenses out of pocket and letting the balance grow tax-free.
High earnersThe Mega Backdoor Roth: Moving Significantly More to Roth
How the Mega Backdoor Roth lets high earners move tens of thousands of after-tax 401(k) dollars into a Roth each year. Plan requirements and timing tips.
Pre-RetireesPre-Retirement Roth Conversions
How retirees can use low-income years before Social Security to convert Traditional IRA balances to Roth — reducing RMDs, Social Security taxation, and IRMAA.
High earnersShifting Assets into Tax-Advantaged Accounts
How to gradually shift taxable savings into 401(k), IRA, HSA, and 529 accounts. Contribution limits, trade-offs, and multi-year strategy for high earners.
Founders & Early Employees
The 83(b) Election: A Tax Strategy for Restricted Stock and Early-Exercise Options
How an 83(b) election lets founders and early employees pay tax now on restricted stock or early-exercise options — locking in low basis and starting the clock.
Founders & employeesSection 1202 QSBS: Tax-Free Gains on Small Business Stock
How Section 1202 lets founders and early employees exclude up to $15M of capital gains. New OBBB Act rules, holding periods, and 409A documentation.
Charitable Giving
Donating Appreciated Assets to Charity: Tax-Smart Giving
How donating appreciated stock to charity avoids capital gains tax, gives you a deduction at fair market value, and amplifies your charitable impact.
Charitable giversDonor-Advised Funds: Giving on Your Timeline
How donor-advised funds let you bunch charitable deductions, donate appreciated stock, automate giving, and grow charitable dollars tax-free before granting.
Tax Planning
Understanding the Additional Medicare Tax
How the 0.9% Additional Medicare Tax works — who owes it on wages and self-employment income, how employer withholding handles it, and how it interacts with NIIT.
High earnersUnderstanding the Alternative Minimum Tax (AMT)
How AMT works, why ISO exercises and SALT deductions trigger it, and which AMT can be recovered as a credit in future years.
Non-payroll IncomeUnderstanding Estimated Tax Payments
When quarterly estimated taxes are due, how underpayment penalties work, and the safe harbor rules for avoiding them. A guide for income without withholding.