The 15 Biggest Tax Mistakes People Make in Retirement

When you prepare for retirement, you expect relaxation, a touch of adventure if you want it, and the chance to enjoy the rewards of your life's labor. But it's not all sunshine and kicking back; you must still deal with taxes.

As retirees embark on this new chapter of life, they can stumble into a labyrinth of tax laws and regulations. Missteps can be costly, hurting hard-earned savings and hampering the fulfillment of retirement dreams.

Here are the 15 biggest mistakes people make in retirement. Avoiding these can help you keep more money in the bank.

Not being organized is a serious issue. If you use a shoebox to store your receipts, you're doing it wrong. Keeping all your tax paperwork together is one of the IRS's top tips to ensure filing goes smoothly.

Thankfully, not being organized is a problem that can be fixed. File folders are cheap and easily labeled. You can also scan your documents to keep digital records, or you can pay someone to do it for you.

Health care expenses can be substantial in retirement. According to Fidelity, the average 65-year-old retired couple may need around $315,000 saved after taxes to cover medical costs.

Some medical costs are deductible. The amount you pay for medical and dental care over 7.5% of your adjusted gross income is deductible. You can deduct 21 cents per mile if you travel to get treatment.

Remember that you'll need to pay federal income taxes on your Social Security benefits, depending on how you file and your combined income. 

For example, if you file as single and your combined income is between $25,000 and $34,000, you'll have to pay income tax on up to 50% of your benefits. That increases to 85% if your combined income is over $34,000.

Nearly half of seniors plan to work part-time or pursue side hustles in retirement to make extra money.

However, the additional income generated may have implications that should be considered to avoid tax surprises. 

Part-time work can impact both your taxes and your Social Security benefits. And freelance gigs on the side don't automatically have taxes taken out, but you will still owe them.

Estate taxes can significantly impact the wealth passed on to your beneficiaries. At the federal level, the IRS threshold for estate tax filing is $13.99 million for 2025, and rates range from 18% to 40%. 

State rules also vary. For example, Hawaii's estate tax ranges from 10% to 20%, and Nebraska has an inheritance tax of up to 15%.

Proper estate planning, including strategies to minimize estate taxes, is crucial for retirees with substantial assets.

Charitable donations can provide both philanthropic fulfillment and potential tax benefits. 

For example, in addition to deducting your donations, you could use your required minimum distribution to contribute to charity straight from your IRA. This can help you avoid the penalty for not taking the RMD and the income tax on that withdrawal.

However, failing to follow the IRS guidelines for deducting charitable contributions can cause your deductions to disappear and increase the risk of a tax audit.

Retirement accounts like traditional IRAs and Roth IRAs have different tax impacts. Withdrawing funds without considering the tax consequences can lead to unexpected tax bills.

Roth IRA withdrawals are tax-free. If you take money out of a traditional IRA before you are 59 1/2, you will get hit with an additional 10% tax on top of income tax.

Retiring to a different state or country can have significant tax implications. Simply put, different states have different tax laws. 

Some, like Florida, have no income or estate taxes but high sales taxes. Others, like Connecticut, have a lot of taxes for retirees.

Ensure you understand the tax laws of the area you relocate to to avoid unforeseen tax burdens.

Once you reach the age of 73, you have to withdraw a minimum amount from your retirement accounts each year, known as required minimum distributions, or RMDs. Roth IRAs don't require withdrawals until the owner's death.

Failing to take these distributions or withdrawing less than the required amount can result in significant penalties: a 50% excise tax on the amount not distributed as required.

Careful planning of retirement account withdrawals can help minimize taxes. You have to look at it strategically and see what works best for you. 

Conventional wisdom might be to pull money from taxable accounts first and Roth accounts last, so there's more time for the funds to grow. But if you have multiple accounts and a steady income, that might not be best for you.

People overlook valuable tax deductions and credits, and it's no different for retirees. For instance, if you or your spouse are 65 and older or blind, you get a higher standard deduction. 

Conversely, if you itemize medical and dental expenses, some taxes and interest expenses can be deducted. When it comes to tax credits that can lower your bill, elderly and disabled taxpayers may be eligible depending on their income.

Talk with a tax professional to make sure you get all the deductions and credits you are eligible for.

Health savings accounts (HSAs) offer retirees a unique opportunity to save for those pricey healthcare expenses tax-free. If you are 55 or older at the end of the tax year, your contribution limit gets bumped up by $1,000.

Failing to take advantage of these tax-advantaged accounts means missing out on potential tax savings.

Converting a traditional IRA into a Roth IRA can offer several tax benefits, like tax-free qualified distributions, avoiding RMDs, and reducing your taxes in the long term.

However, you need to be wary since a Roth conversion increases your taxable income in the conversion year. 

The best option is to talk with a tax pro or financial advisor to evaluate your circumstances and determine if a conversion aligns with your retirement and tax planning goals.

Tax laws are complex and ever-changing. Depending solely on do-it-yourself tax preparation without seeking professional guidance can increase the likelihood of errors and missed opportunities for tax savings.

One of the best ways to avoid these mistakes is to hire a tax professional or a financial advisor specializing in retirement planning. The IRS has an online directory of federal tax return preparers with credentials and specific qualifications.

Taxes on investment gains and dividends can quickly eat into your retirement income. Failing to consider the tax implications of investment decisions can result in diminished returns.

Bond income and certain dividends from stocks and mutual funds are subject to the usual federal income tax rates. On the other hand, long-term gains are typically taxed at lower rates (0%, 15%, and 20%).

Navigating the complex world of taxes in retirement is crucial to protecting your wealth and achieving your retirement dreams. And the biggest retirement tax mistake happens long before actually retiring: failing to plan at all.

You may never be truly free of taxes, but by avoiding these mistakes, you can maximize your retirement income, kick back, and enjoy life.