It is a fair question. AI tools like ChatGPT, Gemini, and Claude are getting better at answering complicated questions, writing legal-sounding documents, and even generating templates for wills and trusts. If you can ask a chatbot to draft your last will and testament for free, why would you pay an attorney to do it?
The short answer: because estate planning is not just about generating a document. It is about making sure that document actually works under the laws of your state, reflects your specific family and financial situation, and holds up when your loved ones need it most. AI can produce a will that looks professional. But looking professional and being legally enforceable are two very different things.
At KLG Estate Planning, we help families across Massachusetts and New Hampshire build estate plans that protect what matters most. Below, we break down what AI can and cannot do when it comes to estate planning, the specific risks you should know about, and why working with a qualified attorney is still the safest path forward.
What AI Tools Can Actually Do for Estate Planning
To be fair, AI is not useless in this space. Tools like ChatGPT can be helpful for general education. They can explain what a revocable trust is, outline the difference between a will and a trust, or summarize how probate works in Massachusetts.
AI can also generate a basic template that resembles a legal document. If you ask ChatGPT to draft a simple will, it will produce something that includes common provisions like naming beneficiaries, appointing an executor, and distributing assets. For someone with no legal background, it might look complete and ready to sign.
But that is where the usefulness ends and the risk begins.
Where AI Falls Short in Estate Planning
Estate planning is one of the most state-specific areas of law. What is valid in one state may be unenforceable in another. AI tools are trained on broad datasets, and they often produce generic outputs that do not account for the specific legal requirements of Massachusetts or New Hampshire.
Massachusetts Has Strict Execution Requirements
Under the Massachusetts Uniform Probate Code (MGL c. 190B, § 2-502), a valid will must be in writing, signed by the testator, and witnessed by at least two individuals. Massachusetts does not recognize holographic (handwritten, unwitnessed) wills. A self-proving affidavit, signed before a notary under MGL c. 190B, § 2-504, can streamline probate, but must follow a specific statutory form.
AI will not walk you through the signing ceremony. It will not tell you who qualifies as a disinterested witness, warn you that a beneficiary who witnesses the will risks voiding their own inheritance, or help you execute a self-proving affidavit correctly. These details matter. If the execution is flawed, the entire document can be challenged or thrown out.
Massachusetts Estate Tax Creates Unique Planning Needs
Massachusetts is one of a handful of states that imposes its own estate tax, separate from the federal estate tax. The state exemption is $2 million per individual. That sounds like a lot until you factor in the value of a home in Greater Boston, retirement accounts, life insurance, and other assets. Many families cross that threshold without realizing it.
The federal exemption, by contrast, sits at $15 million per individual as of 2026 following the passage of the One Big Beautiful Bill Act. That gap between $2 million and $15 million is where Massachusetts families face the most exposure, and it is exactly the kind of nuance that AI tools miss entirely.
A qualified estate planning attorney can help you use strategies like lifetime gifting, irrevocable trusts, and credit shelter trusts to minimize or eliminate Massachusetts estate tax. ChatGPT cannot analyze your specific asset picture and recommend the right combination of tools.
New Hampshire Has Different Rules and Advantages
New Hampshire does not impose a state estate tax or inheritance tax, making it one of the more tax-friendly states for estate planning. However, New Hampshire residents are still subject to the federal estate tax on estates exceeding $15 million. And families who own property in both states, which is common in the Merrimack Valley and southern New Hampshire, need to understand how each state treats those assets.
New Hampshire also updated its homestead exemption laws in 2026, extending protections to trust beneficiaries and increasing the equity protection threshold. If your home is held in a trust, the structure of that trust now directly affects whether you qualify for homestead protections. These are not the kinds of changes that AI tools track in real time.
The Real Risks of Using AI to Create an Estate Plan
AI Can Produce Legally Invalid Documents
AI-generated legal documents have been shown to contain fabricated case citations, incorrect statutory references, and provisions that do not comply with state law. In the legal profession, this is known as “hallucination,” and it happens more often than most people realize. A will that references the wrong statute or includes a clause that conflicts with Massachusetts or New Hampshire law may be unenforceable.
AI Cannot Customize for Complex Family Situations
Estate planning is deeply personal. It involves decisions about blended families, children with special needs, aging parents, business succession, charitable giving, and dozens of other factors that vary from one household to the next. AI tools work from patterns in data. They cannot assess your family dynamics, anticipate potential conflicts, or recommend strategies tailored to your goals.
An attorney might listen to your situation and suggest a supplemental needs trust for a child with a disability, a pour-over will paired with a revocable trust to avoid probate, or a strategy to take advantage of Massachusetts’s lack of a gift tax. These recommendations come from experience and judgment, not algorithms.
Privacy and Privilege Are Not Protected
When you share personal and financial details with an attorney, those communications are protected by attorney-client privilege. When you type the same information into ChatGPT, Gemini, or any other AI platform, that protection does not exist.
In February 2026, a federal judge in United States v. Heppner ruled that documents created by a client using a public AI tool were not protected by attorney-client privilege, even though the client later shared those materials with their lawyer. The court allowed the government to access the AI-generated documents as evidence. For estate planning, where family disputes and tax questions can lead to litigation, this is a serious concern.
You Lose the Most Important Part: The Conversation
Estate planning is not a document production exercise. It is a process that starts with understanding your full financial picture, your family structure, your goals, and your concerns. A good estate planning attorney asks questions you would never think to ask yourself. They identify risks you did not know existed. They help you think through scenarios like what happens if both spouses die at the same time, or what happens to your business if you become incapacitated.
AI skips all of that. It takes your input at face value and generates output based on patterns. It cannot push back, ask follow-up questions, or spot gaps in your thinking.
What AI Can Reasonably Help With
AI is not the enemy of good estate planning. It can serve a useful role when used appropriately. Here are a few ways AI tools can support (but not replace) the estate planning process:
Learning basic concepts. If you want to understand what a durable power of attorney is or how probate works before meeting with an attorney, AI can give you a solid overview.
Organizing your thoughts. AI can help you create a checklist of assets, beneficiaries, and questions to bring to your attorney consultation.
Understanding terminology. Legal language can be intimidating. AI can translate estate planning jargon into plain English so you feel more prepared.
The key distinction is this: use AI to prepare for the conversation with your attorney, not as a substitute for it.
Frequently Asked Questions About AI and Estate Planning
Can ChatGPT write a legally valid will in Massachusetts?
No. While ChatGPT can generate text that looks like a will, a valid Massachusetts will must be in writing, signed by the testator, and witnessed by at least two individuals under MGL c. 190B, § 2-502. AI cannot ensure proper execution, witness selection, or compliance with state-specific requirements like the self-proving affidavit.
Is it safe to use AI for estate planning in New Hampshire?
Using AI to create estate planning documents in New Hampshire carries the same core risks as in any state. While New Hampshire does not impose a state estate tax, families still need to comply with federal estate tax rules, proper will execution requirements, and trust laws that were updated as recently as 2026. AI tools cannot account for these specifics.
What are the biggest risks of using AI to create a will?
The biggest risks include producing a document that is legally invalid, failing to account for state-specific laws, missing critical planning opportunities like tax reduction strategies, exposing sensitive personal information to a platform without privilege protection, and having no professional accountability if something goes wrong.
Does Massachusetts have an estate tax?
Yes. Massachusetts imposes an estate tax on estates exceeding $2 million. Unlike many states, Massachusetts taxes the entire estate once it crosses the threshold, not just the amount above $2 million. The federal estate tax exemption is $15 million per individual as of 2026, so many families owe no federal tax, but still face a significant Massachusetts estate tax bill.
Does New Hampshire have an estate tax?
No. New Hampshire does not impose a state estate tax or inheritance tax. However, New Hampshire residents with estates exceeding $15 million (or $30 million for married couples) are still subject to the federal estate tax. Families who own property in both New Hampshire and Massachusetts should be aware that Massachusetts may tax property located within its borders.
Can I use AI to draft a will and then have an attorney review it?
You can, but most attorneys advise against it. When an attorney reviews an unfamiliar AI-generated document, they cannot verify its accuracy the same way they can with forms and templates they know and trust. It often takes more time and costs more to fix an AI-generated draft than to start fresh with proper legal guidance.
Are AI-generated estate planning documents protected by attorney-client privilege?
No. Communications with AI platforms like ChatGPT are not protected by attorney-client privilege. A 2026 federal court ruling in United States v. Heppner confirmed that documents created using a public AI tool could be accessed as evidence, even if the user later shared them with their attorney. Only direct communications with your attorney are privileged.
Talk to a Massachusetts or New Hampshire Estate Planning Attorney
AI tools are improving every day, and they will continue to play a growing role in how people access legal information. But information is not the same as legal counsel. Your estate plan is too important to leave to a tool that cannot understand your family, your state’s laws, or the consequences of getting it wrong.
If you are in Massachusetts or New Hampshire and want to create or update your estate plan, KLG Estate Planning is here to help. Our experienced attorneys work with individuals and families across Andover, the Merrimack Valley, and southern New Hampshire to build plans that protect your assets, your family, and your peace of mind.
Contact KLG Estate Planning today to schedule a consultation.
This article is for general informational purposes only and does not constitute legal advice. Massachusetts and New Hampshire estate planning laws are subject to change. Consult a licensed attorney for advice specific to your situation.
