November is the month when year-end planning shifts from something you intend to do to something that either happens or does not. The decisions that affect your 2026 tax return, your Medicare premiums in 2028, your Roth balance at retirement, and your portfolio’s alignment with your plan all have a December 31 deadline — hard, immovable, and indifferent to whether you were busy.
This checklist is organized by category and designed to be used directly. Not every item applies to every situation, and the order reflects rough priority — items at the top have the most financial consequence and the most time-sensitivity. Work through what applies to you before the window closes.
Tax and Income Planning
- Project your 2026 taxable income now. Pull together your year-to-date income from all sources: Social Security, pension, IRA distributions, capital gains, interest, dividends, and any Roth conversion amounts already executed. Compare this to the top of your current bracket. The gap between your current income and the bracket ceiling is your planning runway for the next eight weeks.
- Evaluate Roth conversion capacity. With your current income projection in hand, determine how much additional conversion you can execute while staying within your target bracket and below the relevant IRMAA threshold. If you have remaining conversion capacity and the math is favorable, act before December 31. Conversions cannot be undone — and cannot be done retroactively.
- Harvest tax losses. Review your taxable accounts for positions with unrealized losses. Selling at a loss to offset capital gains — or up to $3,000 of ordinary income — is only available during the year in which the loss is realized. Be mindful of the wash-sale rule: you cannot repurchase the same or substantially identical security within 30 days before or after the sale and still claim the loss.
- Realize capital gains strategically. If your income is below the 0% long-term capital gains threshold (approximately $94,050 for single filers, $188,100 for married filing jointly in 2026), you may be eligible to recognize additional gains at zero federal rate. Realizing gains at 0% — and resetting the cost basis — is one of the most efficient available planning moves and requires acting before December 31.
- Execute your Qualified Charitable Distribution. If you are 70½ or older with a traditional IRA and you give to charity, a QCD completed before December 31 satisfies your RMD requirement without adding to taxable income. The annual limit is $105,000 per individual. The deadline is hard — the distribution must be received by the charity before year-end.
Required Minimum Distributions
- Confirm you have taken your full RMD. If you are subject to RMDs (age 73 or older), verify you have taken the full required amount for the year from every account that requires it. The penalty for an RMD shortfall is 25% of the amount not taken, reduced to 10% if corrected promptly. This is not an area for approximation.
- Check inherited IRAs separately. Inherited IRAs have their own RMD rules and their own calculation. If you have an inherited IRA from a parent or other non-spouse beneficiary, confirm the RMD for that account separately from your own. The rules under the SECURE Act are specific and the December 31 deadline applies equally.
Portfolio and Investment Review
- Rebalance to target allocation. If market performance has shifted your portfolio away from your target allocation — equity-heavy after a strong year, or under-allocated after a difficult one — year-end is a natural rebalancing point. Tax-loss harvesting and rebalancing can often be coordinated to minimize the tax cost of making changes in taxable accounts.
- Review the short-term bucket. If you are using a bucket strategy, confirm that Bucket 1 is adequately funded for the next 12 to 18 months of planned distributions. Year-end is the natural time to replenish from longer-term buckets if the near-term cash reserve has been drawn down through the year.
- Review asset location. Are your most tax-inefficient assets — bonds, REITs, high-turnover funds — held in tax-advantaged accounts? Are your most tax-efficient assets — low-turnover index funds, municipal bonds — in taxable accounts? Asset location does not need to be perfect, but meaningful inefficiencies are worth correcting during a rebalancing review.
Insurance and Benefits Review
- Medicare open enrollment closes December 7. If you are on Medicare, the Annual Enrollment Period runs through December 7. This is your window to change Medicare Advantage or Part D plans for 2027. Review whether your current plan still covers your medications at reasonable cost and whether your physicians remain in-network. Missing this window means waiting until January–March for the Medicare Advantage Open Enrollment Period.
- Review life insurance and beneficiary designations. If anything in your family situation has changed this year, confirm that beneficiary designations on all accounts and policies still reflect your intentions. This takes about 30 minutes. The cost of not doing it can be significant and is fully avoidable.
- Flexible Spending Account balances. If you have a healthcare or dependent care FSA through a current employer, confirm the balance and the spend-down deadline. Most FSA funds have a December 31 or March 15 use-it-or-lose-it cutoff. Money left in an FSA at the deadline is forfeited.
Estate and Document Review
- Review your estate planning documents. Has your will, trust, power of attorney, or healthcare directive been updated in the past three to five years? Has anything changed this year — a death, a marriage, a divorce, a new grandchild — that should be reflected? Year-end is a reliable prompt to confirm current status and schedule updates if needed.
- Schedule the conversation you have been deferring. Whether it is the beneficiary designation review, the family legacy conversation, or the estate plan drafting that has been on the list for years — the year ending is the most reliable prompt to act. Make the appointment now, even if the work happens in January.
FAQ: Which Year-End Tax Move Has the Highest Impact?
For most retirees with significant pre-tax IRA balances, the highest-impact year-end move is a Roth conversion sized to use remaining bracket capacity without crossing an IRMAA threshold. This single decision reduces future RMD burden, reduces future tax on growth, and potentially reduces IRMAA premiums for years — and its value compounds over the length of the retirement. The runner-up is the QCD for retirees who are 70½ or older and give to charity: it reduces MAGI rather than simply providing a deduction, producing a more powerful tax benefit that works even for non-itemizers. Tax-loss harvesting and capital gain realization at 0% follow closely, depending on your specific taxable account picture. The item with the most impact in your specific situation depends on your income, bracket position, and account structure — which is exactly what a year-end planning review is designed to identify.
If you want to work through this checklist with someone who can run the specific numbers for your situation — and identify the moves with the most financial impact in the time remaining — that conversation is most valuable now, in November, rather than in December when time pressure compounds.
Schedule a complimentary year-end planning consultation with our office. We will work through your specific tax position, RMD status, portfolio alignment, and any estate planning gaps before the window closes.
