For many donors, the weeks leading up to the tax deadline naturally bring charitable giving into sharper focus. They may have been finalizing contributions, gathering documentation, or coordinating with their CPA to understand how their philanthropy fits into their broader financial plan.
Once the filing deadline passes, it's common for donors to set those decisions aside until year‑end. But for advisors, the period immediately following tax season is one of the most valuable windows to re-engage clients on their charitable strategy while the details, surprises, and conversations are still fresh. This is especially important in 2026 because so many tax laws have changed.
If your clients experienced any surprises this tax season, that's especially worth discussing. Often, small adjustments made early in the year, instead of the final weeks of the calendar year, can lead to better outcomes both financially and philanthropically.
Here are common regrets and how Cambridge Community Foundation can help for the 2026 tax year and beyond.
Giving cash instead of appreciated assets
Many donors regret using cash or credit cards to make large donations instead of gifting appreciated assets (such as stocks, mutual funds, or real estate) held for more than one year.
The regret: Selling assets to donate the cash results in paying capital gains tax on the profit.
The better move: By donating the asset directly to your fund at CCF or to another qualified charity, you may be able to avoid capital gains tax on the appreciation and deduct the full fair market value if you itemize.
Missing out on "bunching" to surpass the standard deduction
The standard deduction was increased under 2017 changes to the tax laws and has stayed high ever since. This can cause missed opportunities for charitable deductions.
The regret: Spreading donations evenly across the years and not exceeding the standard deduction threshold.
The better move: "Bunching" multiple years of donations into a single tax year by using a donor-advised fund at CCF to exceed the standard deduction and claim a tax deduction for that year.
Pro tip: Planning around tax rules is especially important for 2026 and future tax years because not only is the standard deduction still high, but also charitable deductions are now subject to a 0.5% "floor" and a 35% cap. Be sure to talk with your tax advisors early in the year to structure a plan that will work best for you.
Lack of proper documentation
Sadly, many donors fail to keep adequate records, leading to potential deductions being disallowed by the IRS.
The mistake: Failing to get written acknowledgment from the charity for donations over $250, or not having a bank record for smaller cash gifts.
The problem: Without documentation, even genuine donations can be disallowed upon audit.
Honorable mentions
Beyond the "big three," donors also report regrets such as:
–Overlooking IRA Qualified Charitable Distributions (QCDs). Taxpayers 70½ or older forget they can directly donate to charity from their IRAs, which can help satisfy RMD obligations without increasing their taxable income. (Note that changes may be coming that could allow you to use QCDs to fund your donor-advised fund at CCF. Currently, QCDs can fund other types of funds at CCF, but not donor-advised funds.)
–Donating to non-qualified entities. Giving to organizations that are not 501(c)(3) nonprofits, meaning that these donations are not tax-deductible. Working with the experienced team at CCF can help you avoid this pitfall.
Hoping to avoid tax season remorse next year? Please reach out to the team at CCF. We want to be your first call on all matters of charitable giving. Whether you established a fund at CCF years ago, recently became a fund holder, or are considering doing so this year, we are here for you!
With any questions about philanthropic partnerships at CCF, please contact Michal Rubin, VP of philanthropic partnerships, at [email protected]
