As the year winds down, many people are thinking about holiday plans, family gatherings, and completing work projects. However, for retirees and those planning for retirement, financial deadlines carry a special urgency. Tax bills, retirement accounts, and even healthcare costs can be affected by some of these cutoffs. By missing them, you could be losing out on valuable opportunities, or worse, you may face penalties.
The good news? To stay on top of retirement-related deadlines, here are the most important ones you need to know before December 31.
Required Minimum Distributions (RMDs)
A must-do task at year-end for retirees over age 73 (or 72 if you reach that age before 2023) is to take required minimum distributions from traditional IRAs, 401(k)s, and similar tax-deferred accounts.
Why it matters:
As soon as you reach RMD age, you must withdraw a minimum amount every year. It’s a steep penalty if you don’t: 25% of the amount you should have withdrawn — reduced to 10% if you correct it quickly.
What to do:
- Confirm your RMD amount with your financial institution.
- IRA owners with multiple accounts can take their total RMDs from just one IRA. You must take distributions from each 401(k) separately, however.
- Avoid waiting until the last week of December, when hours may be reduced at banks.
Roth Conversions
Do you want to move money from an IRA or 401(k) to a Roth? A Roth conversion is a powerful tax-planning strategy since future withdrawals are tax-free. For the current tax year, however, you have until December 31 to complete a conversion.
Why it matters:
- As you enter retirement, a conversion can protect your tax rate and help diversify your tax exposure.
- When you convert the amount, however, you are subject to ordinary income taxes.
What to do:
- Analyze whether converting is worthwhile based on your current tax bracket.
- To avoid jumping into a higher tax bracket, consider breaking conversions into smaller chunks over several years.
- A tax advisor can help you with this strategy, as it requires careful planning.
Charitable Giving (Including Qualified Charitable Distributions)
If you want your charitable contributions to be considered for this year’s deduction, the year-end is also the deadline. With qualified charitable distributions (QCDs), retirees who are charitably inclined have even more flexibility.
Why it matters:
- If you itemize your deductions, traditional donations can reduce your taxable income.
- You can transfer up to $100,000 per year directly from your IRA to a qualified charity with a QCD for those age 7012 and older. Also, it counts towards your RMD and is not taxable.
What to do:
- Choose between giving cash, appreciated securities, or making a QCD.
- To claim the tax benefit, transfer before December 31.
Flexible Spending Accounts (FSAs)
If you have an employer-sponsored health plan with an FSA and are not yet on Medicare, check your balance. FSAs typically follow a “use it or lose it” rule by December 31, though some plans allow for a grace period or a small rollover.
Why it matters:
Typically, unused funds disappear at the end of the year.
What to do:
- Make those medical appointments you’ve been putting off.
- Be sure to stock up on over-the-counter products that are eligible.
- Verify your employer’s grace periods and rollover policies.
Medicare Advantage and Prescription Drug Plan Changes
During the Medicare Open Enrollment period, which runs from October 15 through December 7, the decisions you make affect your coverage for the following year. As a result, December is an important month to confirm your choices.
Why it matters:
If you miss this deadline, you’ll be locked into your current coverage, with a few exceptions. The result could be higher premiums or prescriptions that are not covered.
What to do:
- Compare your plan’s benefits for 2025 with those of other plans.
- Don’t forget to check your insurance coverage for doctors and prescriptions.
- To avoid surprises in January, submit changes before December 7.
Harvesting Tax Losses (and Gains)
You can offset capital gains or ordinary income up to $3,000 if you sell investments at a loss by December 31, if you have a taxable investment account. Known as “tax-loss harvesting,” this strategy lowers your tax bill.
Why it matters:
When done properly, tax-loss harvesting reduces taxes without significantly altering your investment approach.
What to do:
- With the help of your financial advisor, review your portfolio.
- Identify investments that are underperforming and sell them.
- It’s important to be aware of the “wash sale rule,” which disallows deductions if a substantially identical security is purchased within 30 days.
Maximizing 401(k) and IRA Contributions
Employer-sponsored plans, such as 401(k)s, require you to contribute to your retirement accounts by December 31. Contributions to IRAs, however, can usually be made until the tax filing deadline in April.
Why it matters:
- If you contribute before year-end, you won’t miss out on employer matching.
- In traditional accounts, contributions reduce taxable income for the current year.
What to do:
- Take a look at your contributions so far this year.
- Check with your HR department or benefits department about adjusting your contributions.
Reviewing Beneficiaries and Estate Plans
Retirement accounts, insurance policies, and estate plans can all be reviewed at the end of the year, even if there is no specific deadline.
Why it matters:
In some cases, outdated designations, like former spouses, may override your will and result in family disputes.
What to do:
- Be sure to review all policies and accounts.
- As needed, update beneficiary designations.
- If your life has changed significantly, schedule a meeting with an estate planner.
Health Savings Account (HSA) Contributions
In case you have a high-deductible health plan and are eligible for an HSA, you can contribute until the tax filing deadline. Employers may, however, set internal payroll deadlines in December for employee contributions.
Why it matters:
With HSAs, you can make tax-deductible contributions, grow the fund tax-deferred, and withdraw money tax-free.
What to do:
- If you can, max out your contributions.
- Verify that your employer doesn’t set an earlier contribution cutoff than the IRS.
Key Takeaways
December 31 isn’t just the end of the calendar year — it’s also the end of many retirement planning opportunities. Taking RMDs, donating to charities, and reviewing Medicare coverage all have deadlines that cannot be overlooked.
If you plan early and consult with a financial advisor, you can avoid costly mistakes and optimize your tax strategy.
FAQs
What’s the most important retirement deadline at year-end?
The most common retirement concern for retirees is taking required minimum distributions (RMDs), since missing them can result in penalties.
Can I still make IRA contributions after December 31?
Yes. You typically have until the tax filing deadline — April 15, 2026, for the 2025 tax year. However, 401(k) contributions are usually due by December 31.
Is a Roth conversion worth it before year-end?
It depends on what your current tax bracket is and what your expected tax bracket is in the future. Tax advisors can help you determine if now is a good time to take a tax deduction.
Do I need to act on Medicare by December 31?
The Medicare Open Enrollment period ends earlier — December 7. If you don’t qualify for a special enrollment period, you’re generally locked into your plan for the following year.
What if I miss a charitable giving deadline?
If you want your donation to count for the current tax year, it must be made by December 31. If you miss it, you’ll have to wait until next year’s tax return to claim the deduction.
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