Taxes in Retirement: Which Benefits Are Taxable and Which Aren’t

Published October 28, 2025 Raman Singh, CFP®

Because retirement income isn’t all taxed the same.

Learn how Social Security, pensions, IRAs, Roth accounts, and other income sources are taxed plus find practical, tax-smart strategies to help you keep more of what you’ve earned.

One of the most common questions I hear from people getting close to retirement is this:

“Raman, are my retirement benefits going to be taxed?” It’s a fair question. You’ve worked your whole life, saved carefully, and now you just want to know what’s actually yours to keep.

But here’s the thing though, not all retirement income is taxed the same way. Some sources are fully taxable, some are partially taxable, and some can be completely tax-free if you plan it right. And understanding which is which can make a massive difference in how long your money lasts, and how much ends up with the IRS.

Let’s look at Social Security Income First…

Social Security is usually the first big surprise for retirees. A lot of people assume it’s tax-free, but that’s not always the case. Up to 85% of your Social Security benefits can be taxable depending on your total income. The IRS uses something called provisional income, which includes half of your Social Security benefits plus other income like pensions, IRA withdrawals, and investment income. If you’re a married couple with combined income over $44,000, chances are you’ll be paying taxes on 85% of those benefits.

What you should look out for is how your withdrawals affect that calculation. The order in which you pull from your accounts directly impacts how much of your Social Security gets taxed. When it comes to my clients, I focus on coordinating withdrawals across account types so they can keep more of what they’ve earned. The difference between pulling from the wrong account first and structuring it strategically can easily mean thousands of dollars per year in additional taxes.

And don’t forget the pension income, IRA withdrawals, and 401(k) distributions are almost always fully taxable at your ordinary income rate. That includes your required minimum distributions (RMDs) once you reach the mandated age.

The SECURE 2.0 Act increased the RMD age to 73, and it’ll rise again to 75 in 2033. That gives you a few golden years to do proactive tax planning before RMDs start. One of the best moves you can make in that window is doing partial Roth conversions in your 60s while you still have flexibility.

If you want to understand how that sequencing works, check out my article, Finding Your Safe Withdrawal Rate in Retirement. It explains how timing, taxes, and portfolio balance all work together to help you withdraw confidently without running out of money.

Next up Is, Roth Conversions and the Power of Tax Flexibility

When it comes to my clients, I run detailed Roth conversion analyses every year to find the “sweet spot” and then convert enough to lower future taxes but not so much that it triggers higher Medicare premiums or pushes them into a higher bracket today. If you’d like to see how those conversions really impact your retirement, read my article Retirement Planning Without Taxes: Why It Costs So Much (and How to Fix It). It walks through real examples of how coordinated Roth conversions and bracket management can save retirees six figures over time.

Now, Roth IRAs and Roth 401(k)s are easily the most flexible, tax-efficient accounts in retirement. Once the account has been open for five years and you’re over 59½, your withdrawals are completely tax-free. And, here’s the thing, Roth money doesn’t increase your taxable income, it doesn’t affect your Medicare premiums, and it doesn’t make more of your Social Security taxable. It’s your tax-free paycheck, and it gives you incredible flexibility when markets or tax laws change.

And when I’m building retirement income plans, I use Roth accounts as a stabilizer. It’s the account you can pull from in high-tax years to keep your overall liability low.

Then we have our Investment and Brokerage Accounts which are far too often overlooked.

So let’s talk about your regular brokerage or investment accounts. These accounts can be surprisingly tax-friendly when used strategically. Long-term capital gains and qualified dividends are usually taxed at lower rates — 0%, 15%, or 20%, depending on your income. Municipal bond interest can even be federally tax-free.

So what you should look out for is WHEN you sell. Without planning, you can accidentally trigger large capital gains, bumping your taxable income and increasing Medicare costs. With planning, though, you can use tax-loss harvesting and strategic rebalancing to manage gains and minimize surprises.

And then don’t forget the other Income Sources That Can Sneak Up on You

Annuities, HSAs, and part-time work can all affect your retirement tax picture in different ways.

Annuities, for example, depend on how they were funded. If you bought one with pre-tax dollars, your withdrawals are fully taxable. If you use after-tax money, only the earnings are taxed.

For a deep dive into when annuities actually make sense, read my article Should I Consider an Annuity to Guarantee Retirement Income? I explain when they can genuinely provide peace of mind, and when the fees and tax implications outweigh the benefits.

HSAs, on the other hand, are a triple threat in the best way: tax-free going in, tax-free growth, and tax-free withdrawals for qualified medical expenses. But if you pull money out for non-medical expenses before age 65, you’ll face taxes and a penalty. After 65, non-medical withdrawals are just taxed as ordinary income. And if you plan to work part-time in retirement, keep in mind that those wages are fully taxable and can push more of your Social Security into the taxable range or increase your Medicare premiums.

Lastly…

Most retirees underestimate how much of their “retirement paycheck” goes to taxes. I see it all the time: great portfolios, disciplined savers, but no plan for how to spend their money efficiently. But here’s the thing, without coordination, retirees with over $2Million in Pre-Taxed Savings will end up overpaying through higher Medicare premiums, bracket jumps, or unnecessary taxation on Social Security. And when it comes to my clients, I focus on proactive tax planning by coordinating Social Security timing, withdrawal order, and Roth conversions, so they keep more of what they’ve earned. Taxes are one of the few big expenses you can actually control in retirement, and small adjustments today can mean tens or even hundreds of thousands saved over a lifetime.

That’s exactly why I built Singh PWM as a flat-fee fiduciary firm. No commissions, no percentage of assets, just transparent advice built around your best interests. My goal is simple: to help you minimize taxes, avoid costly surprises, and enjoy a confident, stress-free retirement.

Yes, many retirement benefits are taxable, but how much you pay depends entirely on timing, coordination, and planning ahead. The difference between guessing and having a clear, tax-smart plan can easily add up to high six figures over your lifetime. If you’d like to see exactly how much of your retirement income could be taxable and what strategies can help reduce it, schedule a Retirement Tax Clarity Call today.

Raman Singh, CFP®

Your Personalized CFO

SINGH PWM

Taxes in Retirement: Which Benefits Are Taxable and Which Aren’t

Published October 28, 2025 Raman Singh, CFP®

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