Some of the most valuable tax decisions of your entire year have a hard deadline, and it is not April 15. It is December 31. Once the calendar turns, a whole set of Year-End Retirement Tax Moves that could have saved you thousands of dollars simply expire, unavailable until next year and sometimes gone for good. The last few weeks of the year are when careful retirees quietly lock in savings that careless ones leave on the table, and the difference often comes down to nothing more than acting before the deadline instead of after it.
This is your year-end checklist. It walks through the moves worth considering before December 31, from required distributions and Roth conversions to charitable strategies, gifting, and the income ceilings that can quietly raise your costs. Living in Florida sharpens the focus, because with no state income tax, your federal tax picture is the entire game, a point we cover in depth in our guide to why Florida is tax-friendly for retirees. Read this as an educational checklist, not as individualized tax advice, and run any specific move past your tax professional, because the right answer depends on your full picture. At Roger Fishel Financial we help pre-retirees and retirees across Winter Park, Lake Mary, Lake Nona, Oviedo, Clermont, Winter Garden, and Kissimmee coordinate exactly these decisions each fall. Let us get to the list.
Why Year-End Is the Deadline That Matters For Year-End Retirement Tax Moves
Not every tax move runs on the same clock. A few, like funding an IRA, can be done up until the tax filing deadline in April. But most of the highest-value moves are tied to the calendar year itself and must be completed by December 31 to count for that year. A required distribution not taken, a Roth conversion not executed, a charitable transfer not sent, a loss not harvested: once the year ends, so does the opportunity. That is why the final quarter is such an important planning window, and why it pays to run through your options now rather than in a scramble during the last week of December, when custodians are slammed and processing can take longer than you expect. Start early enough that a transaction has time to actually settle before the year closes.
Take Your Required Minimum Distribution, and Know the New Rules
If you are old enough, the required minimum distribution, or RMD, is the one item on this list you cannot skip. For 2026, RMDs generally begin at age 73, and rise to age 75 for those born in 1960 or later under the phased-in rules. Once you reach your starting age, you must withdraw a minimum amount from your traditional IRAs and most employer retirement plans each year, calculated from your prior year-end balance and an IRS life expectancy factor, and that amount is taxed as ordinary income.
The deadline is December 31, with one exception. Your very first RMD can be delayed until April 1 of the following year, but doing so forces two taxable distributions into that next year, which can spike your income and push you into higher brackets or across the Medicare surcharge lines. For most people, taking the first RMD in the year you turn the starting age is the cleaner choice. Miss an RMD and the penalty is steep: a 25 percent excise tax on the amount you failed to withdraw, though that drops to 10 percent if you correct the shortfall promptly. A couple of finer points matter too. You can aggregate RMDs across multiple IRAs and take the total from any one of them, but 401(k) accounts must each satisfy their own RMD separately. Roth 401(k) accounts no longer require distributions during your lifetime, a welcome recent change. And if you inherited a retirement account, the rules are their own subject: many non-spouse heirs must now take annual distributions and empty the account within ten years, which is worth planning carefully with a professional.
One exception is worth knowing if you are still working past your RMD age. If you remain employed and are not a significant owner of the company, you can generally delay required distributions from that current employer’s plan until you actually retire, though this does not apply to your IRAs or to old plans from former employers. Some people nearing retirement even roll an old 401(k) into their current employer’s plan, where the rules allow, specifically to postpone distributions on that money while they keep working. It is a narrow strategy, but for the working retiree it can defer a chunk of taxable income by design. As with everything on this list, confirm the details with your plan and your tax professional before you rely on it.
Consider a Roth Conversion in Your Low-Tax Window
A Roth conversion means moving money from a traditional retirement account into a Roth, paying income tax on the converted amount now so that it grows and comes out tax-free later. The magic is in the timing. The best years to convert are low-income years, especially the stretch in early retirement after you stop working but before Social Security and required distributions push your income up. Filling up a lower tax bracket with converted dollars in those years can save a great deal over a lifetime, and it shrinks the future RMDs that would otherwise land in higher-taxed years.
Florida makes this especially attractive, because there is no state tax on the conversion, only federal, so the drag that a high-tax state would add simply is not there. But conversions must be done thoughtfully, because the added income in the conversion year can bump into several ceilings at once: it can raise your Medicare premiums two years later, reduce or eliminate a marketplace subsidy if you are under 65, and phase out the temporary senior deduction. It also has a firm December 31 deadline and cannot be undone once completed. This is a move to size deliberately rather than guess at, and our full guide to a Roth conversion strategy for Central Florida retirees walks through how to calibrate it.
Use Qualified Charitable Distributions If You Give to Charity
If you are at least 70 and a half and charitably inclined, the qualified charitable distribution, or QCD, may be the single most efficient move available to you. It lets you send money directly from your IRA to a qualifying charity, and for 2026 you can give up to 111,000 dollars per person this way, or up to 222,000 dollars for a married couple where each spouse uses their own IRA. The transfer counts toward your required minimum distribution, and here is the key: the amount is excluded from your income entirely, not merely deducted.
That distinction is what makes a QCD so powerful. A normal charitable deduction only helps if you itemize, and it never lowers your adjusted gross income. A QCD lowers your income directly, which ripples through everything that keys off income, including how much of your Social Security is taxed and, importantly, your Medicare premiums. For a charitable retiree who has to take an RMD anyway, routing some or all of it to charity as a QCD turns a taxable event into a tax-free gift. A few rules apply: the money must go directly from your IRA custodian to a qualifying public charity, not to a donor-advised fund, and there is a one-time option to direct up to 55,000 dollars into certain split-interest gifts, which counts inside the annual limit. Like most of this list, the deadline is December 31.
Harvest Losses and Gains Deliberately
Your taxable brokerage account offers two year-end moves that retirees often overlook. The first is tax-loss harvesting. If you hold investments that have dropped below what you paid, selling them locks in a loss that offsets your capital gains, and if your losses exceed your gains, you can use up to 3,000 dollars of the excess against ordinary income and carry the rest forward to future years. Just mind the wash-sale rule, which disallows the loss if you buy back the same or a substantially identical investment within 30 days before or after the sale.
The second, and less familiar, move is tax-gain harvesting. In a low-income year, some retirees fall into the 0 percent long-term capital gains bracket, which means they can sell appreciated investments and pay no federal tax on the gain at all, resetting their cost basis higher in the process. Whether either move makes sense depends on your income for the year and your broader plan, and both must be executed before December 31 to count. This is exactly the kind of decision that rewards a look at your whole tax picture rather than a reflex to sell or hold.
One related year-end gotcha catches people in taxable accounts by surprise. Mutual funds typically distribute their capital gains to shareholders late in the year, usually in December, and you owe tax on those distributions even if you reinvest them and even if you bought the fund only weeks earlier. It is worth checking a fund’s estimated distribution before making a large purchase in a taxable account near year-end, since buying just before the distribution date can hand you a tax bill on gains you did not participate in. This does not apply inside an IRA or other tax-deferred account, only in taxable accounts, but there it is an easy and avoidable misstep.
Should You Accelerate or Defer Income? Think Across Years
Year-end planning is not only about lowering income this year. Sometimes the smarter move is to pull income into this year on purpose. The question to ask is not simply how do I pay less tax in December, but how do I pay less tax across the next several years. If this is an unusually low-income year for you, filling up a low tax bracket now, through a Roth conversion or by realizing gains, can be far cheaper than being forced to take that income later in a higher-taxed year, such as once required distributions begin or after a spouse passes and the survivor files as a single taxpayer.
The reverse is also true. If this has been a high-income year, deferring what income you can into next year, and accelerating deductible expenses into this one, may lower the total bill. The right direction depends on how this year compares with the years around it, which is why the best year-end planning looks at a multi-year map rather than a single tax return. For married couples in particular, there is a long-range reason to build tax-efficient income now, because the surviving spouse can later face a higher rate on similar income, a trap we cover in our discussion of the widow’s tax trap. Deciding whether to accelerate or defer is one of the most valuable judgments in the whole year-end process, and it is worth making deliberately.
Extra Moves for Business Owners and Side-Income Retirees
Plenty of Central Florida retirees are not fully retired. They consult, run a small business, rent property, or have a side venture, and that income opens up additional year-end moves worth knowing. If you have self-employment income, a SEP-IRA or a solo 401(k) can shelter a large amount, well beyond the ordinary IRA limit, though the deadlines to establish and fund these plans vary by plan type, so confirm the timing with your tax professional. Self-employment income may also qualify for the qualified business income deduction, which can shield a meaningful slice of that income from federal tax.
Other classic business moves belong on the year-end list too. If you need equipment, buying and placing it in service before December 31 may let you expense it this year. Deductible business expenses you were going to incur anyway can sometimes be accelerated into the current year to lower this year’s income, or deferred into next year if that serves you better, the same accelerate-or-defer judgment discussed above. And if a family member genuinely works in your business, paying reasonable wages can shift income within the family. These are situation-specific and easy to get wrong, so they are worth running past a tax professional, but for the working retiree they can add real savings on top of the personal moves above.
Manage the Income Ceilings That Quietly Raise Your Costs
Here is the theme that ties this whole checklist together. Many of these moves add or subtract income, and several important costs in retirement are triggered when your income crosses specific lines. A well-planned year keeps you on the right side of those lines. An unplanned December transaction can shove you across one and cost you far more than the transaction was worth.
- Medicare surcharges. Higher-income retirees pay an income-related surcharge on their Medicare Part B and Part D premiums, and it works on a two-year lookback, so the income you report for 2026 sets your premiums in 2028. For 2026 the first surcharge tier begins at 109,000 dollars of income for a single filer and 218,000 dollars for a couple filing jointly, and it is a cliff, one dollar over the line triggers the full surcharge for that tier. Our guide to the IRMAA Medicare surcharge covers the details.
- Marketplace subsidies. If you are under 65 and buy coverage through the marketplace, your income determines your premium tax credit, and the subsidy cliff is back in force. A large year-end conversion or withdrawal can erase a subsidy worth thousands, as our fall enrollment guide explains.
- The senior deduction. The temporary deduction for those 65 and older phases out as income rises, beginning at 75,000 dollars for singles and 150,000 dollars for couples. Pushing income too high in December can shrink or eliminate it.
- Social Security taxation. How much of your Social Security is taxed federally depends on your income, so moves that raise or lower income change that too.
The practical rule is simple: before you make a large income move in the final weeks of the year, check where it leaves you against these thresholds. A projection now can be worth thousands. You can read more about the surcharge mechanics in our IRMAA Medicare surcharge guide, and about managing marketplace income in our 2026 fall open enrollment guide.
Max Out What You Can Still Contribute
If you or your spouse are still earning income, even part-time, the end of the year is the time to make sure you have captured every contribution you are entitled to. The 2026 limits are higher than last year’s. You can defer up to 24,500 dollars into a 401(k), 403(b), or similar workplace plan. If you are 50 or older, you can add an 8,000 dollar catch-up, and if you are between the ages of 60 and 63, a larger super catch-up of 11,250 dollars replaces the standard one, letting you defer up to 35,750 dollars in total. A new rule for 2026 requires higher earners to make their catch-up contributions on a Roth basis, which is a change worth confirming with your plan.
Beyond the workplace plan, you can contribute up to 7,500 dollars to an IRA, or 8,600 dollars if you are 50 or older, and you have until the April filing deadline for that one, though it is wise to plan it now. If you are still covered by a qualifying high-deductible health plan, the health savings account remains one of the most tax-efficient accounts in existence, with 2026 limits of 4,400 dollars for individual coverage and 8,750 dollars for family coverage, plus a 1,000 dollar catch-up at age 55 and older. And do not overlook the spousal IRA, which lets a working spouse contribute on behalf of a non-working spouse. Every dollar you shelter is a dollar that grows without an annual tax drag.
Make Your Gifting and Charitable Moves
The end of the year is prime time for giving, both to family and to charity, and several of these moves have tax benefits with a December 31 deadline. On the family side, the annual gift tax exclusion lets you give up to 19,000 dollars per recipient in 2026 without touching your lifetime exemption or filing a gift tax return, and a married couple can combine to give 38,000 dollars per recipient. Gifts like this quietly move money out of your taxable estate while helping the people you love now, when they may need it most. You can also pay someone’s tuition or medical bills directly to the institution without those payments counting against the exclusion at all, and contributions to a 529 college savings plan for a grandchild carry their own advantages.
On the charitable side, beyond the QCD discussed earlier, consider donating appreciated stock rather than cash, which lets you avoid the capital gains tax you would owe if you sold it while still giving the charity full value. If your deductions are close to the standard deduction line, bunching two years of giving into one, often through a donor-advised fund, can push you over the threshold in the year you itemize. These giving strategies connect directly to your broader legacy plan, which we cover in our guide to Florida estate and legacy planning, and year-end is a natural moment to make sure your gifts and your estate documents are pulling in the same direction.
Do Not Forget the Non-Tax Deadlines That Cluster in the Fall
Year-end is crowded with deadlines that are not strictly about taxes but share the same calendar and deserve a place on your checklist. Medicare’s Annual Election Period runs from October 15 to December 7, the window to review and change your Part D or Medicare Advantage coverage for the coming year. If you are under 65 and on a marketplace plan, open enrollment runs into the fall as well. Both are covered in our 2026 fall open enrollment guide. If you have a flexible spending account through work, remember that these are often use-it-or-lose-it, so spend down the balance before it forfeits. None of these are tax moves, but missing them is just as costly as missing a tax deadline, and they all land in the same busy stretch.
Check Your Withholding and Estimated Taxes
A quieter year-end task can save you a penalty. The IRS expects you to pay tax throughout the year, and if you have not paid in enough through withholding or estimated payments, you can owe an underpayment penalty on top of the tax itself. Retirees often trip on this because their income sources changed and their withholding did not keep up. One handy fix: because taxes withheld from an RMD or other distribution are treated as if paid evenly across the whole year, you can use a year-end withholding from a distribution to patch an underpayment that estimated payments would have addressed less cleanly. Reviewing your withholding and estimated payments before year-end, and confirming your final quarterly estimate, is a small step that avoids an annoying and avoidable cost.
If You Recently Moved to Florida This Year
If this is the year you made Florida your home, year-end deserves a little extra attention. For the year of your move, you may still owe a part-year return to your former state on the income you earned while you lived there, and some states are aggressive about claiming departing residents. That makes the timing of large income events especially important. Where possible, it is cleaner to complete a big Roth conversion or a large gain only after you have genuinely established Florida domicile and cut ties with the old state, so that former state cannot try to tax it. Making sure your move is buttoned up, the declaration of domicile, the driver’s license, the voter and vehicle registration, is the foundation that lets you claim Florida’s no-income-tax advantage cleanly, a process we detail in our guide to establishing Florida domicile. Coordinating the move and your year-end income moves together is well worth it in your first Florida year.
Review Your Beneficiaries and Estate Documents
While you have your financial life spread out on the table for year-end planning, take a few minutes for a task that has nothing to do with the December 31 deadline but is easy to keep postponing: review the beneficiary designations on your retirement accounts, annuities, and life insurance. Those designations override your will entirely, and an outdated one, naming an ex-spouse or a deceased relative, is one of the most common and painful estate planning mistakes. Confirm your primary and contingent beneficiaries still reflect your wishes, and while you are at it, make sure your broader documents are current. Our guide to Florida estate and legacy planning walks through the full picture, including Florida’s particular rules. Year-end is as good a prompt as any to keep this from slipping another year.
How These Moves Fit Together
If there is one lesson in this checklist, it is that these moves are not independent. They interact, sometimes in tension. A Roth conversion is a powerful long-term move, but pushed too far it can trigger a Medicare surcharge, erase a marketplace subsidy, and phase out the senior deduction all at once. A qualified charitable distribution lowers your income, which can pull you back under those very same thresholds. Harvesting a gain raises income; harvesting a loss lowers it. The sequence and the size of each move matter, and the best result comes from planning them together as one coordinated year-end strategy rather than making each decision in isolation.
This is precisely where a coordinated approach earns its keep, and where working with a professional who can see your whole tax picture pays for itself. The goal is not to make every move on this list. It is to make the right moves, in the right amounts, in the right order, for your specific situation. That coordination across taxes, income, Medicare, and your estate is the heart of what we mean by why you need a financial quarterback.
A Central Florida Year-End Example
Consider a hypothetical couple in their early seventies in Winter Garden. They have required distributions to take, they are charitably inclined, and they want to keep their income from crossing the Medicare surcharge line two years out. Their year-end plan uses qualified charitable distributions to satisfy much of their required distribution while giving to their church, which keeps that money out of their income and helps hold them under the surcharge threshold. They review their brokerage account and harvest a modest loss to offset a gain they took earlier in the year. They make their annual exclusion gifts to their grandchildren, moving money out of their estate. And because their income is comfortably low this year, they consider a small Roth conversion, sized carefully to fill their bracket without crossing the surcharge line. They also confirm their beneficiary designations and review their Medicare coverage during the fall enrollment window.
None of these moves is dramatic on its own. Together, coordinated and completed before December 31, they meaningfully improve the couple’s tax picture for the year and for years to come. The numbers here are illustrative and every situation is different, but the shape of it is the point. A deliberate year-end plan captures savings that a passive December never sees.
Your Year-End Checklist at a Glance
- Take your required minimum distribution by December 31, and plan the timing of your first one carefully.
- Consider a Roth conversion sized to fill your bracket without crossing key income thresholds.
- Use qualified charitable distributions if you are 70 and a half or older and give to charity.
- Harvest investment losses, and consider harvesting gains if you are in the 0 percent bracket.
- Project your income against the Medicare surcharge, marketplace subsidy, and senior deduction thresholds before any large move.
- Max out 401(k), IRA, and HSA contributions you are still eligible to make.
- Make your annual exclusion gifts and any charitable gifts you have planned.
- Review Medicare coverage during the fall enrollment window and spend down any flexible spending account.
- Check your tax withholding and estimated payments to avoid an underpayment penalty.
- Review your beneficiary designations and estate documents while everything is in front of you.
Bringing It All Together
Year-end tax planning is not glamorous, but few things you do in retirement offer a better return for the time invested. The moves are concrete, the deadline is firm, and in a no-state-tax state like Florida, getting the federal picture right is the whole opportunity. The retirees who come through each year in the best shape are simply the ones who set aside an afternoon in the fall, ran through their options, and acted before the calendar closed the door.
You do not have to sort through all of it alone. Coordinating these moves, and making sure they fit with your income plan, your Medicare, and your estate, is exactly the work we do this time of year, and a single review can pay for itself many times over. The window closes December 31, so the time to look is now, while there are still weeks left to act rather than days.
Make your year-end moves count
If you want a clear, coordinated plan for your year-end tax moves before the December 31 deadline, let us help. We work with pre-retirees and retirees across Central Florida and nationwide to turn this checklist into real savings. book a free year-end tax review with Roger Fishel Financial. Plan. Protect. Prosper.
Frequently Asked Questions
What is the deadline for year-end tax moves?
Most of the moves on this checklist must be completed by December 31 to count for that tax year, including required distributions, Roth conversions, qualified charitable distributions, and tax-loss harvesting. A few, like IRA contributions, can be made up until the April filing deadline. Because processing takes time, it is best to act well before the last week of December.
What age do required minimum distributions start in 2026?
For 2026, required minimum distributions generally begin at age 73, rising to age 75 for those born in 1960 or later. Your first distribution can be delayed until April 1 of the following year, but that forces two distributions into one year, so many people take the first one on time instead. Missing an RMD carries a 25 percent penalty, reduced to 10 percent if corrected promptly.
Can I do a Roth conversion after I start taking RMDs?
Yes, but you must take your required distribution first, and the required amount itself cannot be converted. Conversions are often most valuable in the lower-income years before RMDs and Social Security begin. In every year, size the conversion carefully, because the added income can raise your future Medicare premiums, reduce a marketplace subsidy, and phase out the senior deduction.
What is a qualified charitable distribution and who can use it?
A qualified charitable distribution lets an IRA owner who is at least 70 and a half send money directly from the IRA to a qualifying charity. For 2026 the limit is 111,000 dollars per person. It counts toward your required distribution and is excluded from your income entirely, which lowers your adjusted gross income and can reduce your Medicare premiums and the taxation of your Social Security.
How much can I give tax-free in 2026?
The annual gift tax exclusion for 2026 is 19,000 dollars per recipient, and a married couple can combine to give 38,000 dollars per recipient, with no gift tax and no return required. You can also pay someone’s tuition or medical bills directly to the institution without those payments counting against the exclusion. These gifts also reduce your taxable estate over time.
Does Florida tax any of these year-end moves?
No. Florida has no state income tax, so required distributions, Roth conversions, and capital gains are not taxed at the state level. Only federal tax applies, which is exactly why getting the federal picture right matters so much for Florida retirees, and why careful year-end planning is so valuable here.
How can a year-end move affect my Medicare premiums?
Medicare charges higher-income beneficiaries a surcharge on their Part B and Part D premiums, and it uses a two-year lookback, so the income you report for 2026 sets your premiums in 2028. For 2026 the first surcharge tier begins at 109,000 dollars for a single filer and 218,000 dollars for a couple, and it is a cliff, so a single large year-end transaction can trigger it. Projecting your income before you act is the way to avoid an unpleasant surprise.
What are the 2026 retirement contribution limits?
For 2026 you can defer up to 24,500 dollars into a 401(k) or similar plan, with an 8,000 dollar catch-up at age 50 and older, or an 11,250 dollar super catch-up for ages 60 to 63. The IRA limit is 7,500 dollars, or 8,600 dollars with the catch-up. Health savings account limits are 4,400 dollars for individual and 8,750 dollars for family coverage, plus a 1,000 dollar catch-up at age 55 and older.
Should I try to lower my income every year, or is that the wrong goal?
Not always. The better question is how to pay less tax across several years, not just this one. In an unusually low-income year, deliberately adding income, through a Roth conversion or by realizing gains in a low bracket, can be cheaper than being forced to take that income later at a higher rate. In a high-income year, deferring income may help. It depends on how this year compares with the years around it, which is why a multi-year view matters.
I moved to Florida this year. Does that change my year-end planning?
It can. For your move year you may still owe a part-year return to your former state on income earned while you lived there, and some states scrutinize departing residents. It is generally cleaner to complete a large Roth conversion or gain after you have fully established Florida domicile, so your former state cannot try to tax it. Make sure your domicile steps are complete, and coordinate the timing with a professional.
