Legally Lowering Retirement Taxes: Practical Moves That Hold Up to IRS Scrutiny

Donald Dirren

July 20, 2025

Retirement tax strategies

Navigating retirement taxes can feel overwhelming, especially when trying to balance financial Security with strict IRS rules. But the truth is, retirement tax strategies don’t have to be complicated. With careful planning and wise decision-making, you can reduce your tax liability in retirement while staying fully compliant with the IRS. The goal isn’t to avoid taxes altogether—it’s to minimize them legally and strategically so you can enjoy your retirement without unexpected tax surprises.

Why Retirement Taxes Demand Special Attention

Retirement changes the way income is taxed. You no longer have a single paycheck; instead, you draw from a mix of Social Security, IRAs, pensions, investment accounts, and maybe even part-time work. Each source has different tax rules. Missteps in how you withdraw funds or claim benefits could lead to a much higher tax bill than necessary.

For example, many people assume their tax rate will be lower in retirement. However, once Required Minimum Distributions (RMDs) begin and Social Security benefits are taxed, your income could spike. Add in capital gains or unexpected withdrawals, and suddenly you’re paying more tax than expected. That’s why designing your retirement tax strategies early—and reviewing them annually—can prevent costly surprises later on.

Use Tax Diversification to Stay Flexible

Tax diversification refers to holding money in various types of accounts, including taxable, tax-deferred, and tax-free accounts. This structure allows you to pull income from the best source, depending on your tax bracket, in any given year.

If you rely only on traditional IRAs or 401(k)s, every dollar you withdraw gets taxed at ordinary income rates. By contrast, having funds in a Roth IRA or Roth 401(k) gives you access to tax-free income, which won’t affect your bracket or Social Security taxation. Meanwhile, brokerage accounts offer favorable long-term capital gains treatment.

Having all three “tax buckets” lets you better manage your income and control your tax liability. This flexibility helps you keep your income under certain IRS thresholds, which can lower both federal taxes and Medicare premiums.

Smart Roth Conversion Tactics

One of the most effective retirement tax strategies involves converting funds from a traditional IRA to a Roth IRA. Roth conversions create a taxable event now but eliminate taxes later. Once in a Roth, your money grows tax-free, and future withdrawals aren’t taxed.

The best time to convert is during years when your income is low, such as right after retirement, but before RMDs start. You can “fill up” lower tax brackets without pushing yourself into higher ones. For example, if the 12% bracket ends at $94,300 for a couple, you can convert up to that amount while avoiding higher rates.

Small, consistent conversions over several years are often more valuable than a single large conversion. And always watch for how the conversion impacts your Medicare IRMAA brackets and the taxation of Social Security benefits.

Social Security Claiming Strategies to Reduce Taxes

Social Security isn’t always tax-free. Depending on your “combined income,” up to 85% of your benefits may be taxable. Combined income includes your adjusted gross income, tax-free interest, and half of your Social Security.

One powerful strategy is delaying Social Security until age 70. This not only increases your monthly benefit but also gives you more control over your taxable income in the early years of retirement. During these early years, you can draw from taxable or tax-deferred accounts and even complete Roth conversions without worrying about Social Security taxation.

For retirees who claim benefits earlier, managing how you generate other income—especially capital gains and withdrawals from retirement accounts—is key to staying under the IRS thresholds and minimizing taxation on your benefits.

Order of Withdrawals Can Make or Break Your Strategy

When you start pulling money from your retirement savings, the order matters. Many tax experts recommend beginning with taxable accounts, then transitioning to tax-deferred accounts, and finally utilizing tax-free accounts. This approach delays the tax hit and preserves Roth savings for later in retirement when your tax rate may be higher.

However, if you have a large traditional IRA or 401(k), withdrawing early—even if you don’t need the money—can be smart. Taking small distributions before age 73 helps lower future RMDs, which could otherwise spike your income and Medicare costs later.

Creating a plan that balances your withdrawals to maintain a steady income while minimizing tax spikes is one of the most valuable retirement tax strategies available. Don’t leave this to chance—annual planning is essential.

Tackle RMDs with Proactive Planning

Once you hit the RMD age, you must start taking minimum distributions from traditional IRAs and 401(k)s. These are taxed as ordinary income and can be significant if your balances are high. RMDs can also push you into higher tax brackets or cause up to 85% of your Social Security benefits to be taxed.

One way to handle this is by making Qualified Charitable Distributions (QCDs). If you’re 70½ or older, you can donate up to $100,000 annually from your IRA to charity. This counts toward your RMD but doesn’t increase your taxable income. It’s a win-win for both your tax plan and your favorite cause.

Another method is “RMD smoothing”—drawing down your tax-deferred accounts gradually in your 60s through early distributions or Roth conversions. This prevents a sudden income jump later and gives you more control over your taxes.

Work with a Pro and Keep Good Records

IRS scrutiny often occurs when taxpayers make mistakes, not because they fail to follow the rules. Document every Roth conversion, track your basis in non-deductible IRAs, and keep records of charitable donations and distributions. A well-documented strategy not only lowers your taxes but also protects you during an audit.

Partnering with a retirement-focused tax advisor or CFP can help you avoid common pitfalls and maximize your legal tax benefits. These professionals stay up-to-date on tax law changes and can build custom strategies that protect your retirement nest egg. You don’t have to navigate retirement taxes alone.