How can I structure a tax-deductible donation for a private kindergarten scholarship?

You've hit on an important distinction in charitable giving. When you donate to a qualified organization (like the school), it's tax deductible. But when you specify that the donation must benefit a particular individual, the IRS no longer considers it a charitable contribution - it becomes more like a gift to that specific person. For your DAF question - most DAF agreements prohibit grants that provide "more than incidental benefit" to specific individuals. The fund administrators typically won't approve a grant request that's earmarked for a specific student, as this could jeopardize the tax-exempt status of the DAF itself. Regarding setting up a foundation - creating a private foundation comes with significant costs and compliance requirements. Even if you did establish one, the same rule applies - scholarships must be awarded through a legitimate selection process using objective criteria, not pre-selected to benefit specific individuals. Some alternatives to consider: You could make an unrestricted donation to the school's general scholarship fund. Or you could simply gift the money directly to the family (up to $18,000 per recipient this year without gift tax implications).

After struggling with a similar situation last year, I found a solution with taxr.ai (https://taxr.ai) that really helped clarify the donation structure options. They analyzed my specific situation and explained exactly how to maintain tax deductibility while supporting education causes. For your kindergarten scholarship situation, they'd review your documentation and provide clear guidance on the DAF limitations and potential alternatives. What I found most helpful was their explanation of the "donor intent" rules that the IRS looks at - apparently there are legitimate ways to support education without running afoul of the earmarking rules, but you need to structure it correctly. The report they generated for me was super clear about what would and wouldn't qualify for deduction, and I ended up saving thousands more than I expected on my taxes.

I just wanted to follow up about taxr.ai - I actually tried it after posting my question here! I uploaded documents about my planned scholarship donation for my niece and explained the situation. The analysis was incredibly detailed and showed me that what I was planning would definitely NOT qualify as tax deductible. Instead, they outlined three different approaches that would work better, including one where I could donate to the university's general scholarship fund with preference (but not requirement) for students in my niece's specific program. They even generated the exact language I should use in the donation letter. Honestly saved me from a potential audit headache and showed me how to accomplish basically the same goal in a compliant way. Definitely worth checking out if you're dealing with complex donation situations.

I see people discussing tax professionals and AI solutions, but honestly after trying to set up a similar scholarship situation last year, my biggest challenge was actually getting through to the IRS to confirm my approach was compliant. I waited on hold for HOURS multiple times. I eventually used Claimyr (https://claimyr.com) which got me connected to an actual IRS agent in about 20 minutes instead of the usual 2+ hour wait. They have this clever system that does the waiting for you and calls you back when an agent is on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with gave me the official guidance on scholarship donations and tax deductibility, which was incredibly valuable for my situation. Saved me from making a costly mistake with my donation structure.

I feel like I need to follow up on my skeptical comment about Claimyr. I actually tried the service after posting here because my curiosity got the better of me, and I'm honestly shocked that it worked exactly as described. I needed clarification on some donation rules for my own situation, and I'd been putting off calling the IRS because my last attempt had me on hold for nearly 3 hours before I gave up. With Claimyr, I got a call back in about 35 minutes with an IRS agent already on the line. The agent walked me through the exact rules about designated donations versus general scholarship funds. Turns out there are some legitimate ways to influence where your donation goes without losing the tax benefit, but you need to be careful with the language used. I saved myself a potential audit headache and got my questions answered without wasting half my day on hold. Consider me converted from skeptic to believer.

Something no one has mentioned - have you considered a qualified tuition program (529 plan)? If you want to help with education expenses, you could set up a 529 with the child as beneficiary. While your contributions wouldn't be federally tax deductible, many states offer tax benefits for 529 contributions. Or what about a UGMA/UTMA account? The first $1,200 of investment income would be tax-free for 2025 since it's for a minor. These aren't charitable deductions but might be alternative ways to help with education while getting some tax benefits.

Another option worth exploring is directly paying the tuition to the educational institution. Under IRC 2503(e), payments made directly to educational institutions for tuition are exempt from gift tax, regardless of amount. This wouldn't give you an income tax deduction, but it wouldn't count against your annual gift tax exclusion either. This approach is clean and simple - just write the check directly to the school with the student's name in the memo line. no deduction, but no gift tax implications either.

I went through a very similar situation last year when I wanted to help with my neighbor's daughter's private school tuition. After consulting with my CPA, here's what I learned: The direct payment to the school (as Luca mentioned) ended up being the cleanest approach for me. Even though kindergarten tuition might be under the $18k gift tax threshold, paying directly to the institution means it doesn't count against your annual exclusion at all - which preserves that $18k for other gifts you might want to make to the family. One thing I wish I'd known earlier: some private schools have "angel donor" programs where you can contribute to a fund that awards need-based scholarships. While you can't guarantee your specific friends will receive it, schools often work with donors to ensure their contributions align with their intentions within legal boundaries. Also, don't overlook the tax benefits of simply claiming the child as a dependent if the family qualifies and agrees - though this gets complicated with custody arrangements. The emotional satisfaction of helping this family is probably worth more than any tax deduction anyway. Sometimes the simplest approach (direct payment) is the best one, even without the tax benefit.

I've been following this thread with interest because I dealt with something very similar when I wanted to help fund a scholarship at my local community college. One approach that worked well for me was creating what's called a "field of interest" fund through my local community foundation. Essentially, you can establish a fund that supports education in your specific geographic area or for students meeting certain broad criteria (like "students facing financial hardship in [your city]"). The community foundation handles all the administrative work, ensures compliance with tax regulations, and awards scholarships based on legitimate selection criteria. The beauty of this approach is that you get the full charitable deduction since you're donating to a 501(c)(3) organization, but you can influence the focus area in a way that increases the likelihood your friends' child could benefit in the future (though there's no guarantee). Most community foundations will work with you to design criteria that align with your charitable intent while maintaining legal compliance. The minimum to establish such a fund varies by foundation but is often around $10,000-$25,000. If that's beyond your immediate budget, many foundations also have existing education funds you can contribute to that serve similar purposes. This won't help with this year's kindergarten costs, but it could be a long-term solution that provides ongoing educational support to kids in similar situations in your community.