Year-end retirement checklist for 2026
Most retirement deadlines fall in April, when taxes are due. A few close with the calendar year instead, and once January arrives they can't be done for 2026 at all. The table covers every date in this article. The sections below explain each one.
| What | Deadline | Who it applies to |
|---|---|---|
| Medicare plan changes | December 7 | Anyone on Medicare |
| Marketplace plan for January 1 | December 15 | Under 65 and buying your own coverage |
| 401(k) and 403(b) contributions | Your last paycheck of the year | Anyone still working |
| Roth conversions | December 31 | Anyone with traditional IRA or 401(k) money |
| Required minimum distributions | December 31 | 73 and older (75 if born in 1960 or later) |
| Charity straight from an IRA | December 31 | 70½ and older |
| Selling investments for this year's taxes | December 31 | Anyone with a brokerage account |
| Health FSA balance | December 31, unless your plan allows more time | Anyone with a flexible spending account |
| IRA and HSA contributions | April 15, 2027 | Anyone eligible to contribute |
By December 31
Workplace plan contributions
A 401(k) or 403(b) contribution comes out of a paycheck, so the deadline that matters is the last payday of the year. For 2026 you can put in $24,500, plus $8,000 from the year you turn 50, or $11,250 instead in the years you turn 60 through 63. If your employer matches and you haven't put in enough to get the full match, the part you missed is usually gone. Some plans add it at year end, which your plan documents will say.
Roth conversions
A conversion counts for the year it is completed, and there is no extension into April. Brokerages can take several business days, so a request made on December 30 may land in January and count for 2027. The converted amount is taxed as income this year, which is why it helps to know how much room you have before the next tax bracket.
Required minimum distributions
Withdrawals from traditional IRAs and 401(k)s become required at 73 if you were born from 1951 to 1959, and at 75 if you were born in 1960 or later. Each year's amount is due by December 31. Your first one can wait until April 1 of the following year, but then you take two in that year, both taxed as that year's income.
Missing one costs 25% of the amount that was due, cut to 10% if you take it and file the correction within about two years. The IRS can waive it entirely for a reasonable error that you fix.
Charity, straight from an IRA
From age 70½ you can send up to $111,000 in 2026 directly from an IRA to a charity. It is called a qualified charitable distribution. The money never counts as your income, and once you reach RMD age it counts toward your required withdrawal. The check has to go from the IRA to the charity, not through your bank account, and it has to be out by December 31.
Starting in 2026, people who take the standard deduction can also deduct cash gifts to charity: up to $1,000 for a single filer and $2,000 for a married couple. Gifts count for the year you make them.
Selling investments in a brokerage account
Long-term gains are taxed at 0% while your taxable income stays under $98,900 for a married couple, or $49,450 for a single filer, in 2026. In a low-income year, often the first years of retirement, you can sell investments that have grown, pay no federal tax on the gain, and buy them back at the new price. Losses work the other way: they offset gains, and up to $3,000 a year of other income. Either only counts for 2026 if the sale happens by December 31.
Health flexible spending accounts
Money left in a health FSA is usually lost after December 31. Some employers allow a grace period into March, or let you carry part of it into next year. Your benefits portal shows your balance and which rule your plan uses.
Can wait until April 15
IRA contributions for 2026 can be made until April 15, 2027: up to $7,500, plus $1,100 from age 50.
HSA contributions for 2026 have the same deadline: up to $4,400 with self-only coverage or $8,750 with family coverage, plus $1,000 from age 55. You need to have had an HSA-eligible health plan, and you can't contribute for months you were on Medicare.
When you contribute in early 2027, tell the account provider it is for 2026. Otherwise it counts toward 2027.
Two health-coverage dates in December
Medicare open enrollment ends December 7. It is the window for changing drug plans or moving between Original Medicare and Medicare Advantage. One of those moves is hard to undo, which our open enrollment article explains.
Marketplace coverage starting January 1 needs a plan chosen by December 15 on HealthCare.gov. Open enrollment runs until January 15, but a later choice starts later. Some states run their own marketplace with different dates.
Where your plan fits
Several of these depend on this year's taxable income: how much room a conversion has before the next bracket, and whether gains fall under the 0% line. Your plan shows your taxable income and bracket for every year, this one included.
See this year's taxable income in your plan.
What this doesn't model
- MangoDime doesn't model charitable gifts, qualified charitable distributions, health FSAs, or selling and rebuying investments to use the 0% rate or a loss.
- Limits and brackets here are the 2026 figures. Most change every year, and this page is updated each November.
General information, not investment, tax or legal advice.
Last updated October 30, 2026 · MangoDime