Retirement Tax Planning Guides
Data-driven guides on retirement taxes — every claim sourced from IRS publications, CMS data, and official government sources. Paired with free calculators to run your own numbers.
Essential Guides
Comprehensive guides covering the most important retirement tax topics. Start here.
The 5 Hidden Taxes in Retirement (And How to Avoid Them)
Discover the five taxes that catch retirees off guard — including the Social Security torpedo, IRMAA surcharges, and the ACA subsidy cliff.
ACA Subsidy Cliff 2026: The Complete Guide
Everything you need to know about the ACA subsidy cliff returning in 2026: who's affected, how much is at stake, and strategies to stay below 400% FPL.
Roth Conversions vs. ACA Subsidies: The Impossible Tradeoff
Should you do Roth conversions or keep your income low for ACA subsidies? A framework for the toughest decision in early retirement tax planning.
How to Calculate Your True Marginal Tax Rate in Retirement
Your tax bracket isn't your real rate. Learn how the SS torpedo, capital gains bump zone, IRMAA, and NIIT stack to create effective rates of 40–50%+.
The Social Security Tax Torpedo Explained (With Examples)
A deep dive into the SS tax torpedo: how provisional income works, why marginal rates spike, and proven strategies to escape the torpedo zone.
Deep Dives
Focused articles on specific retirement tax strategies and planning topics.
IRMAA Brackets 2026: What Retirees Need to Know
Complete 2026 IRMAA bracket tables for all filing statuses. See how income affects Medicare Part B and Part D surcharges.
How Roth Conversions Affect IRMAA Medicare Surcharges
Roth conversions can trigger IRMAA surcharges 2 years later. Learn the lookback rules and how to size conversions to avoid bracket jumps.
Tax-Gain Harvesting: The 0% Capital Gains Strategy for Retirees
How to permanently eliminate capital gains tax by harvesting gains in the 0% bracket. The retirement tax strategy most people don't know about.
The Widow's Tax Penalty: What Every Couple Should Plan For
When a spouse dies, the survivor's tax bill can jump $5,000–$20,000/year. Here's why it happens and how to plan ahead.
NIIT: The 3.8% Tax Most Retirees Don't Know About
The Net Investment Income Tax adds 3.8% to investment income above $200K/$250K. Thresholds frozen since 2013 — here's who's affected.
When Should I Start Social Security? Tax Implications
The tax consequences of claiming Social Security at 62, 67, or 70 — and how your claiming age interacts with Roth conversions and the torpedo.
The Best States for Retirement Taxes in 2026
A state-by-state comparison of retirement taxes: income tax, Social Security taxation, estate taxes, and property taxes. With interactive calculators.
2026 Updates
Timely analysis of tax law changes and seasonal planning strategies.
OBBBA Tax Changes: What Retirees Need to Know for 2026
The One Big Beautiful Bill Act made TCJA rates permanent. Here's what changed, what stayed the same, and what it means for your retirement taxes.
SECURE 2.0 Changes for 2026: Roth Catch-Up and Super Catch-Up Rules
Starting 2026, high earners must make catch-up contributions as Roth. Plus the new super catch-up for ages 60–63. Here's what you need to know.
ACA Open Enrollment 2027: Key Dates and Subsidy Rules
When does ACA open enrollment start for 2027? What are the subsidy rules after the cliff returned? Key dates and strategies for marketplace shoppers.
Year-End Tax Moves for Retirees (2026 Edition)
10 tax-saving strategies to execute before December 31, 2026: Roth conversions, tax-gain harvesting, QCDs, and more.
Tools & Comparisons
Product comparisons and guidance on when to seek professional help.
Best HSA Providers for Retirees and Early Retirees (2026)
Compare HSA providers by investment options, fees, and retirement features. Fidelity, Lively, and more — ranked for retiree needs.
TurboTax vs. H&R Block for Retirement Tax Returns (2026)
Which tax software handles retirement income best? We compare TurboTax and H&R Block on Social Security, RMDs, Roth conversions, and more.
Do I Need a Financial Advisor for Retirement Tax Planning?
When DIY isn't enough. Signs you need professional help, what to look for, and how much retirement tax planning costs.
Best Roth IRA Providers for Conversions (2026 Comparison)
Compare Fidelity, Schwab, and Vanguard for Roth conversions. Fees, transfer process, tax reporting, and which makes conversions easiest.