Your Year-End Retirement Checklist: What to Do First and Why

Retired couple at a table reviewing paper statements beside a laptop while working through a year-end retirement checklist.
Most of these items are ones you’ve handled before. The order is what decides how much each one can do, and several of the deadlines land well before December 31.

You’ve probably handled every item on a year-end retirement checklist at some point, and handled each one correctly. Many lists leave out the order, and several of these decisions change what the others can do. 

In early November, you have about eight weeks left in the year, and many custodians stop processing requests by mid-December. Here’s the whole list, in the order we work through it when we do retirement planning for our clients around the Twin Cities area.

What Should Retirees Do Before December 31?

Work through it in this order:

  1. Settle your Roth conversion amount (taking into account the taxable part of this year’s RMD as income).
  2. Check it against Medicare and deduction limits.
  3. Size any tax-loss harvesting.
  4. Take your RMD (or give part of it through a QCD) before you convert.
  5. Bunch charitable gifts.
  6. Finish Medicare open enrollment by December 7.
  7. Check Minnesota’s Social Security subtraction.
  8. Write down how your plan runs.
  9. Scan the routine items.

What’s on a Year-End Retirement Checklist?

What’s on your year end retirement checklist is entirely dependent on the various financial pieces you’ve got in play. That could be a traditional IRA, an old 401(k), Roth accounts, a taxable brokerage account, an HSA, Medicare, Social Security, a pension and even a family cabin. 

The more moving pieces you have, the harder it is to keep everything straight in your head.

In What Order Should I Do Year-End Retirement Tasks?

It typically makes sense to start with the Roth conversion. Moving money from a traditional IRA to a Roth adds to this year’s taxable income, which runs into several ceilings.

  • The Medicare surcharge, called IRMAA: Medicare sets premiums using your modified adjusted gross income (MAGI) from two years prior, so a 2026 conversion counts toward your 2028 premiums. Those future thresholds have not been published yet. For reference, your 2026 Medicare surcharges are based on if your 2024 MAGI above $109,000 for single filers and $218,000 for married couples filing jointly.
  • The health insurance premium credit, if you’re under 65: If you buy coverage through MNsure before Medicare, a conversion can push you past the credit’s income limit. For 2026 coverage, households above 400% of the federal poverty level get no premium credit at all. 
  • The senior deduction: For tax years 2025 through 2028, each spouse who is 65 or older can deduct up to $6,000. Each $6,000 shrinks by 6 cents for every dollar of modified adjusted gross income above $150,000 for married couples filing jointly (or $75,000 for single filers). 
  • Your tax-loss harvesting room: Harvested losses offset capital gains, then up to $3,000 of other income a year, which can open a little more space for a conversion. 

Your conversion decision sets how much space remains for every step after it. That’s the core of year-end tax planning for retirees, and of our tax guidance. 

The Hard Deadlines Come Before December 31

These carry a December 31 date on paper, but many custodians set cutoffs in mid-December, since distributions and check requests need processing time. Ask each custodian for its date.

  • Required minimum distributions (RMDs): RMDs must leave the account by December 31, except in your first RMD year, when you have until April 1 of the following year. If you wait to start until the second year, you will need to take two years’ worth of RMDs in the same year. The year’s RMD comes out before any Roth conversion, so plan the two together.
  • Qualified charitable distributions (QCDs): Starting at age 70½, you can send money straight from your IRA to a charity without adding it to your taxable income. Once your RMDs begin, the gift also counts toward them. The 2026 limit is $111,000 per person. 
  • Charitable bunching: Bunching stacks several years of giving into one, so you itemize that year and take the standard deduction in the others. The 2026 standard deduction for married couples filing jointly is $32,200, plus an extra amount for each spouse 65 or older. Starting in 2026, only gifts above 0.5% of your adjusted gross income count toward an itemized deduction. In the years you don’t itemize, you can deduct up to $2,000 of cash gifts to charity ($1,000 for single filers), though gifts to donor-advised funds don’t count. Combining bunching with a donor-advised fund (DAF) may enable you to spread the money the charity receives over multiple years while preserving the higher itemized charitable deduction for yourself every few years.
  • Tax-loss harvesting: If you sell at a loss and buy the same or a nearly identical fund within 30 days before or after the sale, you can’t claim the loss this year. In most cases, you can still use it later because it’s added to the cost basis of the new shares. If the replacement shares are bought inside a traditional or Roth IRA, though, the loss is gone for good. A sale in early November lets that window close before year-end. A sale on December 28 leaves it open into late January, when an automatic dividend reinvestment can undo the loss.

Medicare Open Enrollment Closes December 7

Medicare open enrollment runs from October 15 through December 7. In early November, that leaves about a month to compare drug plans and Medicare Advantage options. It’s outside the tax chain, so you can work on it now while the tax steps take shape. Minnesota’s Senior LinkAge Line offers free help comparing Medicare plans.

What Year-End Tax Moves Should I Make if I’m Retired in Minnesota?

If you live in Minnesota, your year-end retirement tax checklist needs one more item that national lists leave off: the state’s Social Security subtraction. Minnesota taxes Social Security benefits that are taxable at the federal level, then lets many retirees subtract them back out. 

For tax year 2026, married couples filing jointly with adjusted gross income at or below $110,780 can subtract all of their federally taxable benefits. The single-filer limit is $86,410. Above those amounts, the simplified subtraction drops by 10% for each full or partial $4,000 of adjusted gross income. Minnesota’s worksheet compares this with an alternative calculation and uses whichever gives you the larger subtraction.

That’s why a year-end conversion or a large capital gain can raise your Minnesota tax on Social Security in the same year. The Minnesota Department of Revenue explains how the subtraction works.

Could Someone Else Run This List?

For many couples, one spouse handles the investing and planning while the other handles everything else. A checklist to document the process can help in case the planner is no longer able to manage the year-end tasks.

Does your spouse know where every account is held and who to call? Is your withdrawal order written down anywhere outside your own head? A one-page summary, updated each December, gives whoever steps in a place to start.

Other Periodic Items

Additional periodic checks to consider before year-end:

  • Beneficiary designations on every account and insurance policy
  • Rebalancing, preferably inside IRAs, where trades don’t create a taxable gain
  • HSA contributions, which can wait until the April filing deadline but stop once Medicare starts
  • Next year’s withholding or estimated payments, including January’s if you converted

Start With the Order

Dates and dollar limits shift every year, while the order generally stays the same. Settle the conversion first and test it against the ceilings, then take your RMD before you convert, and let the gifts and harvesting follow.

Would you like a second set of eyes across your whole list? For a 15-minute intro call with our team (no prep required), you can book a time online, call (763) 231-7581, or email info@greatriverfinancial.com. 

Frequently Asked Questions

What happens if I miss my RMD deadline?

You owe a 25% penalty tax on the amount you didn’t withdraw. That may drop to 10% if you withdraw the missed amount and report the tax on Form 5329 within the IRS correction window. The IRS may waive the tax for reasonable error if you are taking steps to correct the shortfall.

Is it too late to do tax-loss harvesting in December?

No, but the timing is tighter. The trade has to happen by the last trading day of the year (Thursday, December 31, 2026). The trade date is what counts for taxes, even if the sale settles in January. The 30-day wash-sale rule applies before and after the sale. Watch for:

  • Automatic dividend reinvestments in January
  • Buying the same fund in another account, including an IRA

A disciplined approach to investment management plans these trades ahead of the year-end rush.

Does Minnesota tax Social Security benefits?

Sometimes. Minnesota taxes benefits that are taxable at the federal level, then offers a subtraction. For 2026, married couples filing jointly with adjusted gross income up to $110,780 can subtract all of it ($86,410 for single filers), and the subtraction phases out above that. At Great River Financial, we include Minnesota tax planning in our bundled fee.

About Josh

Josh Wolberg, CFP®, RICP®, MBA, is President and Lead Financial Planner at Great River Financial, a fee-only financial planning firm based in Plymouth, Minnesota, serving clients across Minnesota and nationwide. With an MBA in finance, he has been a financial advisor since 2007 and has taught CFP® courses as an adjunct instructor since 2010. Josh and the firm’s team of advisors help pre-retirees and retirees turn what they’ve saved into tax-efficient income they can spend with confidence.