How Grandparents Can Help Fund Their Grandchildren’s Education with a 529 Plan
Discover how 529 plans can help support future education costs through tax-advantaged savings, strategic gifting, and long-term planning.
In my first month at Note Advisors, I’ve noticed a wonderful trend: many grandparents are incredibly eager to make a lasting impact on their grandchildren’s education.
Recently, someone asked whether they could contribute appreciated stock directly to a grandchild’s 529 plan to bypass capital gains taxes.
While the short answer is no, it highlights a great opportunity to break down how 529 plans work and how to navigate this exact scenario.
What Is a 529 Plan?
Authorized by Section 529 of the Internal Revenue Code, 529 plans are tax-advantaged savings accounts designed to encourage saving for future education costs. Here are some key benefits of opening one:
Tax Benefits
- Contributions are made with after-tax dollars.
- Earnings grow 100% tax-free.
- Withdrawals are tax-free when used for Qualified Higher Education Expenses.
Diverse Educational Pathways
- Traditional 2- and 4-year public and private colleges and universities
- Graduate programs
- Technical and trade schools
- Registered apprenticeship programs
No Income or Age Restrictions
The beneficiary must be a U.S. citizen or resident alien with a valid Social Security Number (SSN) or Individual Taxpayer Identification Number (ITIN).
Contribution Rules
By law, all 529 contributions must be made in cash or cash equivalents, such as checks, electronic transfers, or payroll deductions. While you cannot transfer stock directly into a 529 plan, there are ways to maximize contributions.
Maximizing Contributions: It’s Per Giver, Not Per Plan
There is no limit on how many different people can contribute to a single child’s plan. The 2026 rules apply to each individual donor:
Annual Exclusion
- Each individual can contribute up to $19,000 per year (or $38,000 for married couples filing jointly) per beneficiary without triggering gift tax reporting.
Superfunding
- An individual can front-load five years of gifts at once—up to $95,000 individually or $190,000 jointly—provided no further gifts are made by that specific donor to that beneficiary for five years.
Lifetime Plan Caps
- Contribution limits vary by state. For example, New York caps the maximum aggregate balance per beneficiary at $520,000.
- Once the cap is reached, no new contributions are allowed from any source, although the account may continue growing through investment returns.
Solving the Appreciated Stock Dilemma
Since you cannot transfer appreciated stock directly into a 529 plan, you have two primary pathways to consider, each with its own tax trade-offs.
Strategy 1: Liquidate and Gift
You can sell the stock, pay any applicable capital gains tax, and contribute the cash proceeds to the 529 plan.
While this approach may create an immediate tax liability, it is often the simplest and most straightforward option. Once the cash is contributed, future growth inside the 529 plan can compound tax-free, and qualified withdrawals for education expenses can also be taken tax-free.
Optimization Strategy: If the stock has appreciated, you may be able to reduce the tax impact by harvesting capital losses elsewhere in your portfolio to offset some or all of the gains recognized on the sale. In certain situations, it may also make sense to spread stock sales over multiple tax years to help manage the overall tax burden.
Although paying capital gains taxes upfront may seem undesirable, it can be worthwhile when weighed against the long-term tax benefits and flexibility that a 529 plan provides.
Strategy 2: Gift Stock Through a Custodial Account
You can gift the stock to a custodial account in your grandchild’s name. Your grandchild assumes your original cost basis, and the stock can later be sold to help fund the 529 plan.
However, there is an important tax consideration.
Many families assume that because the stock now belongs to the grandchild, any capital gains will automatically be taxed at the grandchild’s lower tax rate. In some cases, that is true. However, the IRS has established “Kiddie Tax” rules to prevent families from shifting investment income to children solely to take advantage of lower tax brackets.
As a result, if your grandchild is under age 18 (or under age 24 and a full-time student) and realizes more than $2,700 of unearned income, such as dividends, interest, or capital gains, a portion of that income may be taxed at their parents’ higher marginal tax rate instead of the child’s rate.
There is an important exception for grandchildren who are 18 or are full-time students between the ages of 19 and 23. If they file their own tax return and provide more than 50% of their own financial support specifically through their own earned income, such as wages or self-employment income, they may avoid the Kiddie Tax and instead use their own individual tax rate, which can be as low as 0% for long-term capital gains.
If they do not meet this earned-income support test, you may need to wait until the Kiddie Tax rules no longer apply—generally age 19 for non-students or age 24 for full-time students—before selling the stock.
What Counts as a Qualified Withdrawal?
Funds can be used at qualified colleges, universities, graduate schools, technical and trade schools, and registered apprenticeship programs.
Higher Education & Trade Schools
Qualified expenses include:
- Tuition
- Mandatory fees
- Books
- Supplies
- Equipment
- Computers and internet access used by the beneficiary for educational purposes
Room & Board
Room and board expenses qualify only if the student is enrolled at least half-time and are generally capped at the school’s published cost-of-attendance figures.
Apprenticeships
Qualified expenses include fees, textbooks, and equipment required for participation in a U.S. Department of Labor registered apprenticeship program.
K-12 Tuition
At the federal level, up to $20,000 per year per beneficiary may be used for elementary or secondary public, private, or religious school tuition.
However, New York State treats K-12 tuition withdrawals as nonqualified distributions for New York State tax purposes.
Student Loans
Up to a $10,000 lifetime maximum per beneficiary may be used to repay qualified student loans.
Understanding Adjusted Qualified Education Expenses (AQEE)
Adjusted Qualified Education Expenses (AQEE) are calculated as total qualified education expenses minus any tax-free educational assistance received.
You can only take tax-free withdrawals up to the final AQEE amount. Any withdrawal exceeding AQEE is considered nonqualified, and the earnings portion of the withdrawal is subject to ordinary income tax plus a 10% penalty.
New York State Tax Deduction
Contributions to a New York State 529 plan may help lower your tax bill.
New York taxpayers may deduct:
- Up to $5,000 for individual filers
- Up to $10,000 for married couples filing jointly
Certain limitations may apply depending on each individual’s situation.
Leftover Funds & “What-If” Scenarios
If a beneficiary receives a full scholarship, chooses not to attend college or trade school, or simply has money remaining in the account, the funds are not lost.
Scholarship Exception
You may withdraw an amount equal to the scholarship penalty-free. However, ordinary income tax will still apply to the earnings portion of the withdrawal.
Beneficiary Change
You can change the beneficiary to another qualifying family member, including children, siblings, cousins, spouses, and others.
Maintain the Account
If the beneficiary plans to pursue future education, the funds can remain invested and available for future qualified expenses.
Roth IRA Rollover
If the 529 account has been open for at least 15 years, leftover funds may be rolled directly into the beneficiary’s Roth IRA.
This strategy is subject to:
- A $35,000 lifetime rollover limit
- Annual Roth IRA contribution limits ($7,500 for 2026, or $8,600 if the beneficiary is age 50 or older)
Take a Nonqualified Withdrawal
You may withdraw funds for nonqualified purposes, but the earnings portion may be subject to:
- Federal and state income taxes
- A 10% penalty tax
The original after-tax contributions are treated as a return of capital and are generally not taxable.
Key Takeaways
The Ultimate College Safety Net
529 plans are one of the most effective tools for building a dedicated education fund and helping students graduate without the burden of significant student loan debt.
The Triple-Tax Advantage
Tax-Deferred Growth
- Investments compound tax-free while inside the account.
Tax-Free Withdrawals
- Qualified withdrawals are free from federal income tax and, in most cases, state income tax.
State Tax Benefits
- Many states offer an upfront state income tax deduction or tax credit for contributions.
Significant Flexibility
If the original beneficiary decides not to pursue higher education, you are not locked into one outcome. The beneficiary can be changed to another qualifying family member without triggering taxes or penalties.
No More “Use-It-or-Lose-It” Concerns
Recent tax law changes allow a lifetime limit of up to $35,000 of unused 529 assets to be rolled into a Roth IRA for the beneficiary, potentially giving them a meaningful head start on retirement savings.
If you have questions or need help setting up a 529, don’t hesitate to reach out by either scheduling a call using the button below or emailing us directly at connect@noteadvisor.com.

Andrew Lemay, CPA, MBA, is a Tax & Financial Planning Associate at Note Advisors. He works closely with the firm’s CERTIFIED FINANCIAL PLANNER® professionals to help clients align tax strategy, preparation, and compliance with their broader financial goals. As he works toward earning his CFP® certification, Andrew is committed to delivering the integrated planning experience that is central to Note Advisors’ approach. Connect with him on LinkedIn.
No portion of this commentary is to be construed as the provision of personalized investment, tax or legal advice. Please consult with the appropriate professionals for advice that is specific to your situation. Note Advisors, LLC can assist in determining a suitable investment approach for a given individual, which may or may not closely resemble the strategies outlined herein.












