7 Tax Moves Retirees Will Regret Waiting To Make in 2026
Written by
Jordan Rosenfeld
Edited by
Molly Sullivan
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For many retirees or soon-to-be retirees, tax planning may feel like something they’ll think about when they get there. But delaying certain tax moves in retirement can sometimes lock in higher lifetime taxes, limit future options and create costly surprises years down the road. Financial advisors say some of the biggest regrets come from waiting too long to act.
Here are seven moves retirees will regret waiting to make in 2026.
1. Waiting Too Long To Create a Tax-Efficient Withdrawal Strategy
One of the most common and costliest mistakes retirees make is delaying a coordinated plan for pulling money from different accounts, according to Stephanie Temporiti, wealth advisor at Hightower St. Louis. Without a clear withdrawal strategy, retirees often trigger unnecessary taxes, miss charitable efficiencies and create income spikes that ripple into future tax years. Retirees often experience regret when they realize it’s too late to undo these early decisions.
She recommended working with a tax professional and asking key questions, such as:
- How much will you need on an annual basis?
- What other sources of income will you have?
- How will those income sources be taxed?
- Is there any part of your spending that should come from one type of account vs. another, like charity?
2. Delaying Roth Conversions Until the Window Has Closed
Roth conversions are one of the most time-sensitive tax moves in retirement, able to take place in “a relatively small window of time after retirement — a handful of years at most,” Temporiti said. That window is typically when income is lower and before Social Security and required minimum distributions begin.
Missing that opportunity can mean permanently higher taxes for retirees and for their heirs, who would inherit Roth conversion accounts tax-free, she added.
Worse, “this could mean (missing out on) several hundreds of thousands of dollars passed to the next generation tax-free.”
3. Ignoring Multiyear Tax Bracket Planning
Timing is key when planning for taxes, Temporiti said. Retirees often focus on minimizing taxes year by year instead of looking at income and tax brackets over time. This short-term thinking can lead to higher lifetime taxes, especially for retirees with uneven income streams from business sales, real estate or deferred compensation, Temporiti noted.
“There may be time periods where it makes sense to recognize more income and pay less in taxes or defer income and avoid taxes,” Temporiti said. “Managing tax brackets is a multiyear game.”
She stressed how important it is for retirees to understand what income sources and future liquidity events are in play during retirement.
4. Letting Required Minimum Distributions Dictate Your Taxes
Once required minimum distributions (RMDs) begin, they can complicate delayed tax planning because most retirees don’t know how to effectively begin distributions of taxable RMDs, said Annette Harris, an accredited financial counselor and founder of Harris Financial Coaching.
Without earlier planning, RMDs can push retirees into higher tax brackets, increase Medicare premiums and force withdrawals that weren’t needed for spending. “This can increase taxes for retirees with limited income,” Harris added.
It’s important for retirees to have a clear understanding and projection of what their RMDs are likely to be, Temporiti added, because, “creating a multiyear cash flow plan that reduces RMDs as much as possible is key to not paying any more taxes than you need to.”
5. Missing Charitable Tax Breaks That Must Be Done the Right Way
Many retirees give generously to charity but fail to use the most tax-efficient methods. “Writing a personal check instead of using qualified charitable distributions can leave valuable tax benefits on the table,” Harris said.
“A qualified charitable distribution (QCD) directly from an IRA to a qualified charity can count toward your RMD, and it keeps that amount out of your taxable income,” she advised.
Temporiti also recommended working with a financial advisor to make sure retirees are choosing the right assets to leave to charity through retirement account beneficiary designations or using a donor-advised fund.
6. Not Taking Medicare Premiums Into Consideration
Medicare premiums are based on income from two years prior, which means poorly timed income decisions can increase healthcare costs later, Temporiti explained. Retirees often regret tax moves that seem harmless at the time but trigger higher premiums down the line.
“Downshifting into retirement doesn’t necessarily mean income goes down, and it is important to work with an advisor who is mindful of all your income sources and how they will individually contribute to your income,” she stressed.
7. Failing To Align Tax Planning With Estate Goals
Estate-related tax decisions are among the hardest to fix later. Retirees who delay coordinating Roth conversions, charitable giving and family support often miss opportunities to reduce taxes while supporting heirs more effectively.
“There are many ways to provide financial support that benefit both the parents from an estate planning perspective as well as the adult children,” Temporiti said.
In retirement, the biggest tax regrets often come not from bad decisions, but from waiting too long to make them.
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