How WYCF Can Help: Aspects of Charitable Giving

Tips You Can Trust: Philanthropy in 2026

An Underutilized Asset: Real Estate, Postmark Rule Change, and Women in Philanthropy

Updates from Rachel Bailey, Director of Philanthropy, for Spring 2026

Hello from the WYCF Development Team!  

Thank you for the opportunity to work together. We love hearing from you throughout the year, especially as tax time approaches. We are lucky to work with your clients to maximize their community impact through charitable giving. 

As always, the team at the Wyoming Community Foundation watches trends closely so that we can keep you informed of legal and policy developments that could impact your work with philanthropic individuals. We’re happy to share what’s trending this spring.

• Real estate as an underutilized charitable asset. Although real estate represents a significant portion of many clients’ wealth, it remains one of the least used assets in charitable giving. As property ownership continues to shift across generations and clients reassess underused or burdensome real estate, gifts of appreciated property may play an increasingly important role in philanthropy. Lean on WYCF as you explore key planning considerations, technical requirements, and opportunities for converting real estate into charitable tools. 
• A year-end rule change that caught many people by surprise. If your clients mailed charitable gifts at the end of 2025, the U.S. Postal Service’s change to how postmarks are applied may have real implications for charitable deductions. We will break down what changed, why it matters, and how you can help clients document and, in some cases, preserve deductions they intended to claim for 2025. 
• Women are increasingly shaping the philanthropic landscape—often as primary financial decision-makers and stewards of family legacy. Whether transitions happen gradually or in the wake of loss, the shift is unmistakable. Discover four practical insights to help you better serve women clients and strengthen the charitable strategies you design together. 

Thank you for your partnership. Please consider WYCF as your first call whenever the topic of charitable giving comes up during your client meetings. We look forward to our next conversation! 

-Your friends in philanthropy, WYCF 

Worth a look: Charitable gifts of real estate 

If your client base includes philanthropic individuals, you’re likely aware that gifts of real estate are an option to fund charitable giving. Real estate is the largest asset class in the world, yet various industry sources suggest that only 3% of charitable giving involves gifts of real estate. Still, it’s understandable that charitable real estate donations are often overlooked; the rules and process are complex. Also, many clients struggle emotionally when they start to think about parting with their real estate. 

Things may evolve as real estate ownership changes hands at a fast pace during the major transfer of wealth over the coming years. Gen X and Millennials are expected to potentially inherit trillions of dollars in real estate, which will have a big impact on charitable giving. As more families hold wealth in property rather than cash, philanthropy will involve more non-cash assets. Clients are reassessing properties they already own, like vacation homes that once felt like a dream but now feel underused, costly, or burdensome.  

Given these shifting market dynamics, it is important to be aware of how real estate can support charitable goals in a tax-efficient way. Here are six points to keep in mind: 

1. Gifts of long-term capital assets, including real estate, are typically eligible for a charitable deduction based on the property’s fair market value, rather than its original cost when they’re given to a public charity. You’ll want to confirm that the property qualifies as a long-term capital asset, since the fair market value deduction is available only for property held for more than one year. 
2. Your clients can make gifts of real estate to a donor-advised or other type of fund at WYCF. Because WYCF is a public charity, when the property is sold, the proceeds can flow into the fund without triggering capital gains tax. This allows a client to convert an illiquid or burdensome asset into a flexible charitable resource that can support causes they care about. 
3. Before your client gifts real estate, please reach out to the development team at WYCF to help evaluate the viability of the gift, and offer options for the types of funds to receive the proceeds so your client meets their charitable goals.  
4. Additional considerations include confirming that the property is not restricted by a mortgage or debt, which can complicate the gift, evaluating whether depreciation recapture or unrelated business income tax could apply, and determining whether environmental due diligence is required.  
5. As is the case with any gift of an illiquid asset, documentation and process are critical. Your client must obtain a qualified appraisal to establish fair market value and properly report the gift on Form 8283, and the transfer must be completed using appropriate legal documents, including a deed. 
6. You’ll also want to ensure that the client has not prearranged a sale of the property (even through casual conversations), which could jeopardize the deduction under the IRS’s anticipatory assignment of income rules or step transaction doctrine.  

Although the technical requirements can seem daunting, the payoff of a real estate gift can be substantial for your client and the community. WYCF is here to help with the charitable aspects of all types of gifts, and real estate is no exception. 

Postmarks, rule changes, and remedies for clients’ 2025 charitable gifts 

If you were surprised to read about the ripple effect of a seemingly small change in the U.S. Postal Service regulations late last year, you were not alone! Here’s what you need to know, including potential remedies for your clients whose 2025 charitable deductions may be impacted by this change. 

What’s the background with the IRS? 

Under long-standing IRS guidance, a charitable contribution is generally considered “made” for tax purposes when the donor irrevocably parts with control of the gift. For contributions made by check and sent through the mail, the IRS has traditionally treated the date of the USPS postmark as the date of the gift, even if the charity receives the check later. This approach is reflected in IRS Publication 526 and generally parallels the broader “mailbox rule” under Internal Revenue Code Section 7502, which treats certain documents and payments as timely based on their postmark date rather than the date of receipt.  

Okay, so if this is not an IRS issue, what happened? 

In November 2025, USPS (not the IRS) changed how postmarks are applied. Effective December 24, 2025, the official postmark date is now defined as the date of the first automated processing scan at a USPS processing facility, rather than the date a letter is dropped in a mailbox or handed to a clerk at a local post office. So, mail deposited on December 31, 2025 may not have received a postmark until several days later, especially around the holidays. This change took many people by surprise and created a lot of confusion, prompting the USPS to issue a “facts and myths” circular.  

So what’s this got to do with the IRS? 

Because the IRS’s practices continue to rely on the postmark to establish the date of a mailed charitable gift, this change can cause a contribution a client intended to deduct for 2025 to be treated as a 2026 contribution if the postmark reflects a January processing date. 

If my client got caught up in this change, is the client totally out of luck for a 2025 charitable deduction?  

Not necessarily. The underlying IRS rules governing charitable contribution timing have not changed. Publication 526 still requires your clients to “substantiate” or document—the date of their gift, and the IRS continues to look at objective evidence to determine when the contribution was made. What has changed is the ability to rely on an envelope postmark as proof of a year-end gift. (Advisors should understand that the statutory mailbox rule in Section 7502 is primarily directed at tax filings and payments to the IRS, but in practice the IRS uses similar concepts when evaluating the timing of gifts, particularly where the postmark is the primary evidence of mailing.) 

Okay, it sounds like all is not lost. What should I do to help my client? 

If a client was caught up in this rule change at the end of 2025, the first step is to gather and preserve any alternative proof that establishes when the gift was mailed. Documentation such as a USPS Certificate of Mailing, a certified or registered mail receipt, or a manually applied postmark or postage validation imprint obtained at the retail counter can help prove that the donor relinquished control of the gift before year-end, even if the automated processing postmark is later. Even where the client has such postal documentation, other records such as copies of the check, the client’s notes, and any correspondence with the charity should also be kept in case the deduction is questioned.  

What should clients do for 2026 and beyond?  

Advisors should help clients avoid this issue going forward. Electronic giving methods such as online donations, ACH or wire transfers, and completed transfers of publicly traded securities provide clear and accurate timestamps for deduction purposes and do not depend on postal processing practices.  

How can WYCF help? 

Reach out to our team early in the year! Many clients find themselves rushing at the end of the year to make gifts. The change in the postal rules is a great reason to remind a client that organizing charitable giving through a donor-advised fund at WYCF allows them to make a donation for tax purposes to the donor-advised fund before the end of the year, so they can secure any applicable charitable deduction.

Women and philanthropy: Four insights to inform your practice 

At WYCF, we’re honored to work with many people who support a wide range of charitable causes. The generosity and commitment across generations and demographics inspire our team every single day.  

March is an especially good time to reflect on the evolving role of women in philanthropy because it’s Women’s History Month. Increasingly, women are leading charitable decisions in their families, especially as more women are serving as primary financial decision-makers, according to Indiana University’s Lilly Family School of Philanthropy’s Women Give 2024: 20 Years of Gender & Giving Trends.  

Two scenarios are driving this change: 

1. In many families, a leadership shift happens gradually. For example, a daughter becomes more engaged over the years in conversations about the family’s charitable giving. Or a spouse who once deferred philanthropic decisions begins to shape priorities more directly.  
2. In other cases, the transition is sudden and personal—often following the death of a spouse or parent—when a woman assumes sole responsibility for stewarding both financial assets and charitable intent. 

Here are some examples of how your awareness of these trends can play out day-to-day: 

Help your clients give through thick and thin. 

According to the Women Give 2024 study, over the past two decades, single women experienced a smaller decline in charitable participation than single men, and their average giving amounts held steadier or increased in certain contexts (e.g., secular causes during COVID-19). Be aware of this trend as you represent single women; it may be a priority for them to continue giving even when times are tough. WYCF can help you develop a charitable giving plan to enable women-led philanthropy to continue through life’s ups and downs. 

Discuss national trends and local needs.  

According to the Women’s Philanthropy Institute at Indiana University’s Lilly Family School of Philanthropy, for the first time, between 2022 and 2023, giving to women’s and girls’ organizations surpassed 2% of overall charitable giving. This represents over $11 billion going to women’s and girls’ organizations each year. However, when adjusted for inflation, the amount decreased between 2021 and 2023. This trend is worth mentioning to clients, especially with the help of the development team at WYCF to share parallel local trends and opportunities to make an impact. 

Ask about all forms of philanthropy. 

According to the 2025 Bank of America Study of Philanthropy: Charitable Giving by Affluent Households, 43% of affluent households volunteered in 2024, up from 37% in 2022—volunteers tend to give more and support causes more deeply, a trend stronger among women. Ask these clients about causes they support both financially and through volunteering.  

Tailor advice for single women. 

Research shows that participation trends vary by household type, with single women maintaining more consistent giving patterns over long periods. Pay attention to building thoughtful charitable giving plans for single women households. WYCF can help maximize both impact and financial planning goals for these clients. 

As is the case when you are working with any charitable client, our team is honored to be your partner. We are here to help ensure their giving reflects both enduring legacy and evolving purpose. 

The team at the Wyoming Community Foundation is a resource and sounding board as you serve your philanthropic clients. We understand the charitable side of the equation and are happy to serve as a secondary source as you manage the primary relationship with your clients. This newsletter is provided for informational purposes only. It is not intended as legal, accounting, or financial planning advice.