The check is…NOT in the mail?

This article is part of our philanthropic briefing series for professional advisors.

Lost checks. Stolen checks. Delayed checks. And now, effective December 24, 2025, the U.S. Postal Service has changed how it defines the official postmark date, which could impact the timing of when checks mailed to nonprofits “count” for IRS charitable deduction purposes. All of this provides an important opportunity to remind clients about the benefits of supporting their favorite charities in ways other than writing a check.

In the nonprofit world, challenges with checks are not new, but it’s been a tough nut to crack. Despite the rise of digital tools, many donors still default to writing checks. While checks feel simple and familiar, they introduce real friction for both donors and charities, including not only mailing delays, but also processing costs, security risks, and administrative inefficiencies.

Here are three ways your clients can shift their support to favorite charitable causes.

Use a donor-advised fund

Suggest that your clients centralize charitable giving through a donor-advised fund with an entity like Fairfield County’s Community Foundation. This DAF option offers a more streamlined and intentional alternative to writing checks. A donor-advised fund allows a client to consolidate philanthropy in one place, make a single contribution (or a series of contributions), and then recommend grants to charities over time. This approach reduces paperwork, simplifies recordkeeping, and creates a clear structure for giving that can evolve with the client’s priorities.

Give appreciated stock

Advisors can add significant value by reminding clients to look beyond cash when making charitable gifts. For example, many clients hold highly appreciated stock, yet they continue to write checks to charity out of habit. Donating appreciated securities directly to a donor-advised fund or other qualified charity can be far more tax-efficient. When structured properly, the client may be able to avoid capital gains tax on the appreciation while still receiving a charitable deduction for the fair market value of the asset. This often results in a larger gift to charity at a lower after-tax cost to the donor, a result that aligns perfectly with both philanthropic and financial planning goals.

Give online

If your client prefers to continue to give directly to favorite charities, remind the client that giving online is faster and more reliable than writing a check, ensuring that a donation is received and credited immediately without the delays, loss risks, or processing uncertainties that come with mail. Online gifts also create a clear digital record with automatic receipts, making it easier for clients (and you!) to substantiate charitable contributions for tax purposes. For charities, online giving reduces administrative costs and allows staff to focus more resources on mission-driven work rather than manual check processing.

By gently reminding clients about alternatives to check-writing, you are helping them make the most of their giving. As always, the Community Foundation team is here to assist you as you advise your philanthropic clients. Contact Joe Collin, VP of Philanthropy, at JCollin@FCCFoundation.org or call us at (203) 750-3200.