• Menu
  • Skip to right header navigation
  • Skip to main content
  • Skip to primary sidebar
  • Skip to footer

Call us today for help! (860) 548-1000

  • Facebook
  • Instagram
  • LinkedIn
  • Twitter
  • YouTube

Site Logo

Estate Planning | Making a Difference One Family at a Time

  • Home
  • Who We Are
    • About Our Firm
    • As Seen on TV
    • Careers
    • Client Testimonials
    • Meet Our Team
    • Special Olympics Sponsorship
  • How We Can Help
    • Asset Protection & Business Planning
    • Estate and Gift Tax Figures
    • Estate Planning
    • LGBTQ Estate Planning
    • Loss of a Loved One
    • Minor Children and Young Adult Planning
    • Outdated Estate Planning Documents
    • Pet Planning
    • Powers of Attorney
    • Powers of Attorney, Health Care & Emergency Documents
    • Probate
    • Remarriage and Blended Families Protection
    • SECURE Act
    • Special Needs Planning
    • Trust Administration 
  • Elder Law
    • Alzheimer’s Disease
    • Caregiver Information
    • Elder Law Reports
    • Emergency Medicaid & Nursing Home Planning
    • Guardianship & Conservatorship
    • Hospice Care
    • Medicaid Planning
    • Options for Paying for Nursing Home Care
  • Resources
    • Complimentary Estate Planning Worksheet
    • Complimentary Medicaid/Long-Term Care Calculator
    • DocuBank
    • Elder Law Resources
      • Glastonbury Elder Law Resources
    • Estate Planning Articles
    • Estate Planning Checkup
    • Estate Planning Presentations
    • Estate Planning Techniques
    • Frequently Asked Questions
      • Asset Protection and Business Planning FAQs
      • Business Succession Planning FAQs
      • Digital Estate Planning
      • Elder Law & Medicaid FAQs
      • Estate Administration FAQs
      • Estate and Gift Tax FAQs
      • Estate Plan Revisions
      • Estate Planning FAQs
      • Estate Planning for Blended Families
      • Estate Planning for Young Families FAQs
      • Family Heirloom Planning
      • Families Without an Estate Plan FAQs
      • Incapacity Planning FAQs
      • In-Home Elder Care FAQs
      • IRA Inheritance Planning FAQs
      • Irrevocable Trusts FAQs
      • LGBTQ Estate Planning FAQs
      • Living Trust FAQs
      • Medicaid Planning FAQs
      • Nursing Home Asset Protection FAQs
      • Outdated Estate Planning Documents FAQs
      • Probate FAQs
      • Probate Avoidance FAQs
      • SECURE Act 2.0 FAQs
      • Trust Administration FAQs
      • Wills FAQs
    • Medicaid Planning Checklist: Preparing for Your Long-Term Care Consultation
    • Newsletters
    • Probate Resources
    • Published Books
    • Reports
      • Advanced Estate Planning
      • Basic Estate Planning
      • Estate Planning for Niches
      • Trust Administration
    • Trust Administration Checklist
    • Year-End Estate Planning Checklist
  • Seminars
  • Communities We Serve
    • Fairfield County
      • Darien
      • Greenwich
      • Fairfield
      • Stamford
      • Westport
    • Hartford County
      • Avon
      • Glastonbury
      • Hartford
      • Simsbury
      • West Hartford
    • Litchfield County
      • Watertown
    • Middlesex County
      • Middletown
      • Old Saybrook
    • New Haven County
      • Middlebury
      • New Haven
    • New London County
      • Groton
      • Old Lyme
      • Stonington
    • Tolland County
      • Mansfield
    • Windham County
      • Woodstock
  • Review Us
  • Blog
  • Contact Us
  • Home
  • Who We Are
    • About Our Firm
    • As Seen on TV
    • Careers
    • Client Testimonials
    • Meet Our Team
    • Special Olympics Sponsorship
  • How We Can Help
    • Asset Protection & Business Planning
    • Estate and Gift Tax Figures
    • Estate Planning
    • LGBTQ Estate Planning
    • Loss of a Loved One
    • Minor Children and Young Adult Planning
    • Outdated Estate Planning Documents
    • Pet Planning
    • Powers of Attorney
    • Powers of Attorney, Health Care & Emergency Documents
    • Probate
    • Remarriage and Blended Families Protection
    • SECURE Act
    • Special Needs Planning
    • Trust Administration 
  • Elder Law
    • Alzheimer’s Disease
    • Caregiver Information
    • Elder Law Reports
    • Emergency Medicaid & Nursing Home Planning
    • Guardianship & Conservatorship
    • Hospice Care
    • Medicaid Planning
    • Options for Paying for Nursing Home Care
  • Resources
    • Complimentary Estate Planning Worksheet
    • Complimentary Medicaid/Long-Term Care Calculator
    • DocuBank
    • Elder Law Resources
      • Glastonbury Elder Law Resources
    • Estate Planning Articles
    • Estate Planning Checkup
    • Estate Planning Presentations
    • Estate Planning Techniques
    • Frequently Asked Questions
      • Asset Protection and Business Planning FAQs
      • Business Succession Planning FAQs
      • Digital Estate Planning
      • Elder Law & Medicaid FAQs
      • Estate Administration FAQs
      • Estate and Gift Tax FAQs
      • Estate Plan Revisions
      • Estate Planning FAQs
      • Estate Planning for Blended Families
      • Estate Planning for Young Families FAQs
      • Family Heirloom Planning
      • Families Without an Estate Plan FAQs
      • Incapacity Planning FAQs
      • In-Home Elder Care FAQs
      • IRA Inheritance Planning FAQs
      • Irrevocable Trusts FAQs
      • LGBTQ Estate Planning FAQs
      • Living Trust FAQs
      • Medicaid Planning FAQs
      • Nursing Home Asset Protection FAQs
      • Outdated Estate Planning Documents FAQs
      • Probate FAQs
      • Probate Avoidance FAQs
      • SECURE Act 2.0 FAQs
      • Trust Administration FAQs
      • Wills FAQs
    • Medicaid Planning Checklist: Preparing for Your Long-Term Care Consultation
    • Newsletters
    • Probate Resources
    • Published Books
    • Reports
      • Advanced Estate Planning
      • Basic Estate Planning
      • Estate Planning for Niches
      • Trust Administration
    • Trust Administration Checklist
    • Year-End Estate Planning Checklist
  • Seminars
  • Communities We Serve
    • Fairfield County
      • Darien
      • Greenwich
      • Fairfield
      • Stamford
      • Westport
    • Hartford County
      • Avon
      • Glastonbury
      • Hartford
      • Simsbury
      • West Hartford
    • Litchfield County
      • Watertown
    • Middlesex County
      • Middletown
      • Old Saybrook
    • New Haven County
      • Middlebury
      • New Haven
    • New London County
      • Groton
      • Old Lyme
      • Stonington
    • Tolland County
      • Mansfield
    • Windham County
      • Woodstock
  • Review Us
  • Blog
  • Contact Us

How Does a Generation-Skipping Trust Work?

April 24, 2025 //  by Diana O'Rourke, Estate Planning Attorney

generation-skipping trustWhen your assets exceed the exemption amount ($13.99 million in 2025), estate taxes can significantly erode your legacy as wealth moves between generations. As a response, you could consider a generation-skipping trust (GST) to ease the burden. Let’s look at the details.

What Exactly Is a Generation-Skipping Trust?

A generation-skipping trust is a specialized trust designed to transfer wealth directly to grandchildren or later descendants, bypassing your children’s generation for tax purposes.

When you pass assets directly to your children, those assets are taxed at the point of transfer. Then, when your children pass away, another round of taxation will enter the picture.

Using a GST, you place assets into a trust that will eventually distribute assets to your grandchildren. Your children can benefit from the income or limited distributions during their lifetimes, but they never directly control or own the principal.

As a result, the principal isn’t subject to estate taxes upon their deaths. By strategically “skipping” your children, you minimize taxation and optimize your wealth as it moves across generations.

Generation-Skipping Transfer Tax (GSTT)

The IRS imposes a special tax known as the generation-skipping transfer tax. It is designed to limit the wealth that can pass directly from grandparents to grandchildren tax-free. This tax applies to transfers made through direct gifts, inheritances, or trusts that skip a generation.

Though this tax is a factor, the same $13.99 million exemption applies, so there is still a window of opportunity. With careful and early planning, you can maximize your exemption and ensure you’re not losing a significant portion of your wealth to unnecessary taxes.

Who Should Consider a Generation-Skipping Trust?

You should seriously consider a generation-skipping trust if your estate exceeds or is approaching the exemption threshold. These trusts aren’t usually needed if your estate falls comfortably below this limit.

They are primarily beneficial for families looking to preserve significant wealth over multiple generations.

Structuring Your Trust

When creating your GST, you have significant flexibility. You can structure distributions in various ways, providing income or limited access to principal for your children while ensuring your grandchildren ultimately inherit the trust assets.

You can also decide on specific conditions for distributions to your grandchildren. For example, you might provide funds only when they reach certain ages, achieve educational milestones, or meet other criteria you choose.

Your trustee plays a key role in managing the trust. You can appoint a trusted family member, friend, or professional trustee who will follow your instructions to the letter.

Professional Guidance Is Essential

Because generation-skipping trusts involve complex tax rules and substantial amounts of money, they require careful legal drafting. Any missteps can trigger unintended taxes or fail to achieve your goals.

Working with an estate planning attorney ensures your trust aligns with your financial situation, family dynamics, and personal objectives. Our firm is fully prepared to help you devise a tax efficiency strategy if you are a high-net-worth individual.

At the same time, we are here to provide the necessary guidance if taxes won’t be a source of concern. Even if you are not extremely wealthy, different approaches can be taken. When you work with us, your plan will be finely tailored to suit your specific needs.

Attend an Upcoming Educational Event!

We host seminars that cover all the most important topics in an easy-to-understand way. Our attorneys get a lot of positive feedback at these events, and they are offered on a complimentary basis, so this is a great opportunity. To see the dates and learn more, visit our Special Events Page.

Need Help Now?

To schedule a consultation at our Westport or Glastonbury, CT estate planning offices, call us at 860-548-1000 or send us a message through our contact page.

  • Author
  • Recent Posts
Diana O'Rourke, Estate Planning Attorney
Diana O'Rourke, Estate Planning Attorney
Associate Attorney at Nirenstein, Horowitz & Associates, PC
In May 2023, Diana M. O’Rourke joined Nirenstein, Horowitz & Associates, P.C. as an associate attorney in the trust administration department. Diana has five years of experience practicing in the areas of estate administration, estate planning and elder law.She is admitted to practice in the State of Connecticut and is a member of the Connecticut Bar Association, where she is part of the Estate & Probate section and the Elder Law section...Read More!
Diana O'Rourke, Estate Planning Attorney
Latest posts by Diana O'Rourke, Estate Planning Attorney (see all)
  • What Is a Pour-Over Will and Why Do I Need One? - August 13, 2026
  • Family Loans: Should They be Addressed in Your Estate Plan? - August 4, 2026
  • Can You Refuse an Inheritance? - July 2, 2026
Spread the love

Category: Estate PlanningTag: estate tax efficiency, advanced estate planning, generation-skipping trust

Previous Post: «trusts, QTIP Tools in the Kit: Exploring Different Types of Trusts
Next Post: Can an Irrevocable Trust Be Changed? irrevocable trust»

Search

Blog Subscription

Our blog gives you the most up-to-date estate planning news. Sign up today to receive our regular updates!

This field is for validation purposes and should be left unchanged.
Untitled

Connect With Us Today!

  • Facebook
  • Instagram
  • LinkedIn
  • Pinterest
  • Twitter
  • YouTube

Glastonbury Office Address

Somerset Square
200 Glastonbury Boulevard, Suite 202
Glastonbury, CT 06033-4418
Phone: (860) 548-1000
Fax: (860) 761-1070

Map

Nirenstein, Horowitz & Associates P.C. Somerset Square Google Maps

Westport Office Address

Westport Office
8 Wright Street, Suite 107
Westport, CT 06880
Phone: (860) 548-1000
Fax: (860) 761-1070

Map

Nirenstein, Horowitz & Associates P.C. Westport Office Google Maps

Office Hours

Monday8:30 AM - 5:00 PM
Tuesday8:30 AM - 5:00 PM
Wednesday8:30 AM - 5:00 PM
Thursday8:30 AM - 5:00 PM
Friday8:30 AM - 5:00 PM

Our Law Offices

Nirenstein, Horowitz & Associates P.C.
SOMERSET SQUARE

200 Glastonbury Boulevard, Suite 202 Glastonbury, CT 06033-4418

Phone:(860) 548-1000

Fax: (860) 761-1070

See Larger Map

Westport Office

8 Wright Street, Suite 107
Westport, CT 06880
Phone: (860) 548-1000
Fax: (860) 761-1070

( By appointment only )

See Larger Map

Office Hours

Monday8:30 AM - 5:00 PM
Tuesday8:30 AM - 5:00 PM
Wednesday8:30 AM - 5:00 PM
Thursday8:30 AM - 5:00 PM
Friday8:30 AM - 5:00 PM

Sign Up for Our Newsletter

Sign up to get our complimentary estate planning newsletter for all our tips and resources.

This field is for validation purposes and should be left unchanged.

  • Advantages of Working With Our Firm
  • About The American Academy
  • Disclaimer
  • Privacy Policy
  • Sitemap
  • Contact Us

Copyright © 2026 American Academy of Estate Planning Attorneys | All Rights Reserved