Giving, Raises and Renewals: Your Fall Checklist

For many of our clients, generosity sits near the top of things that matter most to them. Supporting a church, a school, a local cause, or a family in need is about as clear an expression of values as money can make.

This fall, giving deserves a fresh look. The tax rules for charitable gifts changed on January 1, 2026, and the changes help some givers and quietly cost others. At the same time, retirees face two annual decisions: a new Social Security cost-of-living adjustment and Medicare open enrollment. Here is what to know about each, and what to do before the year ends.

The One Big Beautiful Bill Act, signed in July 2025, made three changes to the charitable deduction that took effect this year. Which ones matter to you depends mostly on whether you itemize.

If you...	What changed	What it means
Take the standard deduction	New deduction of up to $1,000 ($2,000 married filing jointly) for cash gifts to public charities	For the first time since 2021, non-itemizers get a tax benefit for giving. Gifts to donor-advised funds don't qualify.
Itemize	Only gifts above 0.5% of your adjusted gross income are deductible	On $200,000 of income, the first $1,000 of giving produces no deduction.
Itemize and are in the 37% bracket	The tax benefit of itemized deductions is capped at 35%	Each dollar given saves at most 35 cents in federal tax, down from 37.

For most households, the new non-itemizer deduction is good news. Roughly nine in ten taxpayers take the standard deduction, and until now their gifts have brought no tax benefit at all. The 0.5% floor works the other way. It trims a little from every itemizer's deduction each year, rewarding larger, less frequent gifts.

Four Ways to Give Smarter Under the New Rules

The new rules don't change why you give. They do change how to give most efficiently.

•         Bunch your gifts. Instead of giving the same amount every year, combine two or three years of giving into one. In the giving year, you clear the 0.5% floor and itemize. In the off years, you take the standard deduction, plus the new $1,000 or $2,000 deduction for any cash gifts.

•         Use a donor-advised fund to bunch without changing what charities receive. You contribute several years of giving to the fund at once and take the deduction that year. Then you recommend grants to your favorite charities on your usual schedule. The charities see no difference.

•         Give appreciated stock instead of cash. If you itemize, donating shares you've held more than a year lets you deduct their full market value and never pay capital gains tax on the growth. It is one of the most efficient ways to give.

•         Give directly from your IRA if you're 70½ or older. A qualified charitable distribution (QCD) sends money straight from your IRA to a charity, up to $111,000 per person in 2026. It isn't deductible, but it never shows up as income, so the 0.5% floor and the 35% cap don't apply. Once you reach the required minimum distribution age, a QCD also counts toward your RMD. Lower reported income can reduce Medicare premiums too, which brings us to our next topic.

For Retirees: Your Raise and Your Renewal

Social Security's 2027 raise. The Social Security Administration announced next year's cost-of-living adjustment of 3.7%, with the increase starting in January 2027 payments.

Medicare premiums. Part of that raise will go to Medicare. The standard Part B premium is $202.90 a month in 2026. Medicare's trustees projected about $209.50 for 2027, and the official number usually arrives in November. Higher-income retirees pay an extra surcharge, known as IRMAA, based on income from two years earlier. Your 2027 premiums depend on your 2025 tax return, and your 2026 income will set your 2028 premiums. That is why the timing of Roth conversions, large capital gains, and charitable gifts from your IRA all matter.

Medicare open enrollment, October 15 to December 7. This is your one window each year to change Part D drug plans or Medicare Advantage plans. Plans change their premiums, covered drugs, and pharmacy networks every year, so last year's best plan may not be this year's. The cap on what you pay out of pocket for covered drugs rises from $2,100 in 2026 to $2,400 in 2027. A 20-minute review on the Medicare.gov Plan Finder, with your current prescriptions in hand, is often worth hundreds of dollars.

Before December 31

•         Decide this year's giving strategy. Will you bunch this year, give from your IRA, or take the new standard-deduction benefit? If you're considering a donor-advised fund or a gift of stock, let us know by mid-November, so there is time to complete the transfer.

•         Make your QCDs directly from your IRA. If you're 70½ or older, the money must go straight from the IRA to the charity, not through your checking account.

•         Review your Medicare drug or Advantage plan by December 7.

•         Check your 2026 income before year-end. Roth conversions and capital gains this year will affect your Medicare premiums in 2028.

The last quarter of the year is always a good time to update and review our tax projection and see what the consequences of any last-minute tax moves are.  As always, we would be happy to meet with you and make sure your checklist is complete before 2027.