To receive a deduction or other tax benefit, charitable contributions must generally be made during the calendar year in which the deduction is claimed. That means ensuring checks are mailed or electronic transfers are processed before December 31, in accordance with the One Big Beautiful Bill Act regulations.

But beyond timing, how you give matters as much as when you give. Since the 2017 Tax Cuts and Jobs Act increased the standard deduction, far fewer taxpayers itemize deductions, which can affect their overall tax liability. That means some charitable gifts no longer provide a direct tax benefit unless donors plan strategically.

A structured year-end giving plan can:

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  Help reduce adjusted gross income (AGI) and potential Medicare surcharges.
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  Make your charitable gifts more tax-efficient—whether you itemize or not.
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  Support your legacy and estate planning goals.
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  Provide you with more flexibility in timing and control over your donations.

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  Reduces taxable income — QCDs don’t count as income, helping to keep your AGI lower.
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  Can help avoid Medicare surcharges — A lower AGI may reduce exposure to IRMAA thresholds.
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  Counts toward RMDs — You satisfy part or all of your required distribution while supporting causes you value.
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  No need to itemize — Even if you take the standard deduction, QCDs can still reduce taxes.

The concept of “bunching” allows donors to combine several years of charitable giving into a single year to exceed the standard deduction threshold—then take the standard deduction in alternate years.

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  Evaluate whether bunching makes sense based on your expected deductions and income level.
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  Factor in the potential timing of other major expenses (medical, property taxes) that affect itemization.
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  If using a DAF, confirm account setup and transfer deadlines before mid-December.

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  Immediate deduction when you contribute to the fund.
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  Tax-free growth of the account while you decide which charities to support.
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  Flexibility in timing donations to specific organizations.
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  Streamlined record-keeping—you track only the initial DAF contribution for tax purposes.

Donating appreciated securities—such as stocks, mutual funds, or ETFs—can often be more tax-efficient than giving cash.

When you donate appreciated assets held for more than one year, you can generally deduct the fair market value of the gift and avoid paying capital gains tax on the appreciation.

Some retirees seek to integrate philanthropy into their estate planning and long-term financial strategies to mitigate the impact of the estate tax. Vehicles such as Charitable Remainder Trusts (CRTs) or Charitable Gift Annuities (CGAs) can achieve both income and legacy objectives, but they require careful structuring and professional guidance.

A CGA involves donating assets to a charitable organization in exchange for a guaranteed lifetime income stream. After your lifetime, the remaining funds will be donated to charity.

These vehicles are best suited for donors with significant appreciated assets or complex estates and should be reviewed with your financial, legal, and tax advisors before implementation.

Charitable giving is deeply personal—but it’s also an essential component of a well-designed financial plan, especially when considering Roth IRA distributions. At Goldstone Financial Group, we help retirees and pre-retirees structure giving strategies that align with their income needs, tax efficiency, and legacy goals.

Our advisors can help you:

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  Evaluate whether QCDs, DAFs, or appreciated securities make sense for your situation.
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  Coordinate with your tax and estate planning professionals to ensure compliance with IRS rules.
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  Build a charitable strategy that supports both your financial security and the causes that matter most to you.
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  Identify ways to give strategically without jeopardizing retirement income or cash flow.