Your End-of-Year Retirement Checklist: Tax Moves Before Dec 31, 2026

The final weeks of the year can feel hectic, but for retirees and near-retirees, they represent a genuine window of opportunity. Many of the most powerful tax-planning moves in retirement are time-bound: they must happen before December 31 or the chance is gone for another twelve months. Some carry meaningful penalties if skipped entirely.

This checklist covers the seven most important year-end tax moves for 2026, from satisfying your Required Minimum Distribution to reviewing your Medicare premium exposure. Each item is grounded in current IRS and SSA rules. Work through them with your tax professional or financial adviser to understand which ones are relevant to your situation.

If you turned 73 or older before 2026, you are generally required to take a minimum distribution from your traditional IRA and most employer-sponsored retirement accounts (such as a 401(k) or 403(b)) by December 31, 2026. This rule comes from the IRS under the SECURE 2.0 Act, which raised the RMD starting age to 73 for people who reach that age after December 31, 2022.

The penalty for missing an RMD is significant. Under current IRS rules, failing to take your full RMD results in a 25% excise tax on the shortfall. That penalty drops to 10% if the mistake is corrected within two years under the IRS self-correction window. Either way, it's a costly oversight that's worth avoiding.

A few important nuances to be aware of:

• First-year exception: If 2026 is your first RMD year (you turned 73 in 2026), you technically have until April 1, 2027 to take it. However, delaying means taking two distributions in 2027, which could push you into a higher tax bracket.
• Still working? If you are still employed and participating in your current employer's 401(k), a plan provision may allow you to delay RMDs from that specific account past age 73. This does not apply to IRAs or accounts from previous employers. You can learn more in our guide to the still-working exception for RMDs.
• Inherited IRAs: If you inherited an IRA, different rules apply depending on when the original account owner died and your relationship to them. The 10-year rule introduced by the SECURE Act significantly changed inherited IRA planning.

Your plan administrator or IRA custodian can provide your calculated RMD amount. The IRS also publishes life expectancy tables in Publication 590-B that form the basis of the calculation.

A Roth conversion involves moving money from a traditional IRA (or pre-tax 401(k)) into a Roth IRA. The converted amount is added to your ordinary income for the year, so you pay income tax on it now. In exchange, that money grows tax-free in the Roth account and is not subject to future RMDs.

Why December 31 matters: A conversion completed by December 31, 2026 counts as 2026 income. Conversions completed on January 1, 2027 or later count as 2027 income. This makes the timing decision meaningful if your income varies year to year.

Year-end Roth conversions are often worth exploring when:

• Your 2026 income is lower than you expect in future years (for example, you retired mid-year).
• You have room in your current tax bracket before hitting the next rate threshold.
• You want to reduce the size of future RMDs by shrinking your traditional IRA balance.
• You are concerned about the Social Security tax torpedo, where rising income causes more of your Social Security benefits to become taxable.

One important consideration: the converted amount increases your Adjusted Gross Income (AGI), which can affect other thresholds, including IRMAA (covered below) and the taxability of your Social Security benefits. A tax professional can run a projection to show the full picture before you act. The IRS provides guidance on Roth conversions in Publication 590-A.

If you hold investments in a taxable brokerage account, December 31 is the last day those trades can count toward your 2026 tax return. Two related strategies are worth understanding:

Tax-loss harvesting involves selling positions that are currently worth less than you paid for them. The realized loss can offset capital gains elsewhere in your portfolio, and up to $3,000 of net losses can offset ordinary income in a given year (IRS Publication 550). Any losses beyond that carry forward to future years.

One important rule to keep in mind: the IRS wash-sale rule (IRC Section 1091) prevents you from claiming a loss if you buy the same or a substantially identical security within 30 days before or after the sale. The loss is deferred, not eliminated, but the timing must be managed carefully.

Tax-gain harvesting works in the opposite direction. If your 2026 income falls within the 0% long-term capital gains bracket (which applies to taxable income up to $47,025 for single filers and $94,050 for married filing jointly in 2024, per IRS guidance, with 2026 amounts adjusted for inflation), selling appreciated positions may generate zero federal tax on those gains. This can be a useful way to reset your cost basis on holdings you plan to keep long term. Our detailed article on the 0% capital gains bracket explains how this works in practice.

Both strategies require settlement. Stock trades generally settle in one business day (T+1), so trades placed in the final days of December should settle well before year-end, but it's worth confirming with your broker.

For 401(k), 403(b), and most employer-sponsored plans, contributions must come from your payroll. That means December 31 is the effective deadline for 2026 plan contributions, since your last paycheck of the year determines what you can contribute.

The IRS sets the following 2024 contribution limits (2026 limits will be adjusted for inflation and announced by the IRS in late 2025 or early 2026):

• 401(k) / 403(b) employee deferral: $23,000 per year (2024), or $30,500 if you are age 50 or older.
• Super catch-up contribution (ages 60-63): Under SECURE 2.0, savers aged 60-63 may contribute an even higher catch-up amount beginning in 2025. Our article on the super catch-up provision covers the details.
• IRA contributions: Unlike 401(k)s, traditional and Roth IRA contributions for 2026 can be made up until the tax filing deadline in April 2027. However, funding them before year-end gives the money more time to grow.

If you are self-employed, the contribution deadlines vary by plan type. SEP-IRA contributions can generally be made up to the business tax filing deadline (including extensions), while SIMPLE IRA and Solo 401(k) rules differ. Our guide to self-employed retirement plans covers the specifics for each plan type.

If you are age 70½ or older and charitably inclined, a Qualified Charitable Distribution (QCD) is one of the most tax-efficient tools available. A QCD allows you to transfer money directly from your IRA to an eligible 501(c)(3) charity, up to $105,000 per individual in 2026 (adjusted annually for inflation per the IRS). The transferred amount is excluded from your taxable income entirely.

For those subject to RMDs, a QCD can satisfy all or part of your RMD obligation without the distribution appearing in your AGI. This matters for several reasons:

• Lower AGI may reduce the portion of your Social Security benefits subject to federal tax.
• Lower AGI may help you stay below IRMAA income thresholds (see item 7 below).
• The QCD achieves a charitable deduction equivalent even if you take the standard deduction, since the income is simply never counted in the first place.

To count for 2026, the QCD must be completed and the check cashed by December 31. The IRS provides QCD guidance in Publication 590-B, and your IRA custodian can typically facilitate the transfer directly to the charity.

The federal standard deduction for 2024 is $14,600 for single filers and $29,200 for married filing jointly (IRS Rev. Proc. 2023-34), with 2026 amounts adjusted for inflation. For many retirees, itemizing deductions no longer provides an advantage over the standard deduction, which means smaller annual charitable gifts may generate no additional tax benefit.

One approach some donors consider is bunching: concentrating two or more years of charitable giving into a single tax year to push total itemized deductions above the standard deduction threshold. In years when they do not bunch, they take the standard deduction.

Donor-Advised Funds (DAFs) are a common vehicle for this approach. A donor contributes a lump sum to the DAF before December 31 and receives the full charitable deduction in 2026. Grants to specific charities can then be distributed from the DAF over multiple years according to the donor's schedule. DAFs are offered through many financial institutions and community foundations.

Cash contributions to public charities are generally deductible up to 60% of AGI, while appreciated securities donated directly to a DAF or charity may allow the donor to deduct the fair market value while avoiding capital gains on the appreciation (subject to AGI limits). The IRS covers charitable contribution rules in Publication 526.

IRMAA stands for Income-Related Monthly Adjustment Amount. It is a surcharge that higher-income Medicare beneficiaries pay on top of their standard Part B and Part D premiums. The surcharge is determined by your Modified Adjusted Gross Income (MAGI) from two years prior. This means your 2026 income will directly affect your Medicare premiums in 2028.

The Social Security Administration applies IRMAA automatically based on your tax return filed with the IRS. For 2024, the standard Medicare Part B premium is $174.70 per month, with IRMAA surcharges that can add significantly more for higher earners (CMS, 2024 Medicare Costs fact sheet). The 2026 thresholds will be updated by CMS, but the bracket structure is expected to follow the same general pattern.

Income events that can unexpectedly trigger or increase IRMAA include:

• A large Roth conversion.
• Required Minimum Distributions from a large traditional IRA.
• Sale of a business, property, or concentrated stock position.
• Receipt of a pension lump sum.

If your 2026 income is approaching an IRMAA bracket, projecting where you will land before December 31 gives you time to consider whether any adjustments are worth exploring. Conversely, if your income has dropped significantly due to retirement or other changes, you can request a reconsideration from the SSA using Form SSA-44 if a life-changing event is involved.

This article is provided for general educational purposes only and does not constitute personalised financial, tax, or investment advice. Every individual's financial situation is different, and the moves described here may or may not be appropriate for your circumstances. Consult a qualified financial adviser, CPA, or tax professional before making any financial decisions, particularly those involving RMDs, Roth conversions, or charitable giving strategies.