The Dangers of AI-Drafted Estate Plans

By Michael J. Rose, Attorney, Rose Elder Law, LLC

AI can write you a will in about thirty seconds. Whether that will actually works is a different question, and you will never know the answer. Your family will.

I understand why people are trying it. The tools are free or inexpensive. They are fast and they sound like a lawyer. Search interest in "DIY wills" has grown sharply over the past year. For people with very simple circumstances, a basic form may be sufficient. But I have practiced estate planning in Oregon for many years, and I have seen what happens when a plan that looked fine on paper meets real life. Here is what concerns me about handing this job to an AI tool.

AI sounds confident even when it is wrong

AI tools are designed to give you an answer that sounds right. That is not the same as an answer that is right. They confuse rules from different states. They cite statutes that do not exist. They borrow language from California or Texas for a document meant for Oregon. And they do all of it in the same calm, polished tone.

If you are not a lawyer, you cannot tell the difference. That is the problem. A mistake in an email is embarrassing. A mistake in a trust can send your house to the wrong person.

Oregon signing rules: a will only works if it is signed correctly

Oregon has specific rules for how a will must be signed. It must be in writing, signed by you, and witnessed by two people who also sign. Oregon does not accept handwritten, unwitnessed wills the way some states do. Trusts, powers of attorney, and deeds each have their own signing and notary requirements.

An AI tool may hand you a polished document and say nothing about any of this. Or it may give you the rules for a different state. If the signing is wrong, your family may end up in court asking a judge to accept the will anyway. That is possible in some cases, but it takes time, money, and evidence. It is exactly what you were trying to avoid.

The document is only part of the plan

This is the mistake I see most often, with or without AI. People sign a trust and believe they are finished. They are not.

A revocable living trust controls only the assets actually in it. Your house must be deeded to the trust. Your bank and brokerage accounts must be retitled. Your retirement accounts and life insurance pass by beneficiary designation, not by your will or trust. If those designations are out of date, they still control distributions.

You can have a well-drafted trust and still end up in probate, or still have a former spouse named on your 401(k). An AI tool can draft the document. It will not record your deed, contact your bank, or confirm who is named on your IRA.

AI does not know what it does not ask

A good estate planning meeting is mostly questions. AI answers what you type. It does not know what you left out, and it rarely pushes back.

Here are some situations where a generic document can cause real harm:

• Blended families. If you leave everything to your spouse, your children from a prior marriage may receive nothing if your spouse later changes his or her own plan.
• A child or grandchild with a disability. Leaving money to them outright can disqualify them from SSI or Medicaid. A properly drafted special needs trust avoids that problem.
• Long-term care. If you or your spouse may need nursing home or assisted living care, how your plan is set up can affect Medicaid eligibility. Oregon's rules here are technical, and they change.
• Minor children. Who raises them and who manages their money are two different decisions. Children generally cannot receive assets outright until they reach adulthood.
• Property in more than one state. Real estate outside Oregon can mean a second probate if it is not handled correctly.
• A family member who might contest. If someone is being left out, or getting less, how the plan is drafted and signed matters a lot.

None of these are rare. Most families I meet have at least one of these issues.

Be careful what you type in

To get a useful document, you have to give the AI tool a lot of personal information. Your assets. Your account balances. Your health. Family conflicts. Your children's names. Depending on the tool and its settings, that information may be stored or used in ways you did not expect.

When you talk with an attorney, those conversations are confidential and generally protected by attorney-client privilege. A chat window does not offer that protection.

The mistakes do not surface until it is too late

Here is the difficult part about estate planning. You never see whether your plan works. It is tested after you have died or lost capacity. By then, you cannot fix it, and you cannot explain what you meant.

I have helped families clean up after do-it-yourself plans have gone wrong. That usually means a probate that was never supposed to happen, a court petition to interpret unclear language, or siblings who stop speaking to each other. Fixing a bad plan almost always costs more than doing it right in the first place. Often far more.

Should you use AI for estate planning at all?

Yes. Just use it for the right job. I am not anti-technology. AI is a useful way to learn the vocabulary. You can ask it what a pour-over will is, or what a successor trustee does. You can use it to make a list of your assets and your questions before you meet with an attorney. That makes your meeting faster and more productive.

What I would not do is let it draft the documents your family will rely on. That is especially true if any of these apply to you:

• You own a home or other real estate
• You have children from more than one relationship
• You have a family member with a disability or special needs
• You or your spouse may need long-term care
• You have retirement accounts or life insurance with beneficiary designations
• You own property in more than one state
• You expect someone might be unhappy with your plan

If even one of those fits you, it is worth talking with an estate planning attorney.

Frequently asked questions

Can I use AI to write my will in Oregon?

You can, but the document still has to meet Oregon law. Oregon requires a will to be in writing, signed by you, and signed by two witnesses. An AI tool may not tell you that, or it may give you the rules for another state. Even a properly signed will can fail if the language is unclear or does not fit your family.

Is a will written by ChatGPT or another AI tool legally valid?

Who drafted the will does not determine whether it is valid. How it is signed and witnessed does. The bigger risk is what the will says. AI tools can leave out key provisions, use terms from another state, or miss issues like a child with special needs or a blended family.

What is the most common mistake with a do-it-yourself trust?

Failing to fund it. A revocable living trust controls only the assets titled in its name. If your house is never deeded to the trust and your accounts are never retitled, your family may still face probate.

When should I hire an estate planning attorney instead of using AI?

You should talk with an attorney if you own real estate, have children from more than one relationship, have a family member with a disability, may need long-term care, own property in more than one state, or expect someone to challenge your plan.

How we can help

At Rose Elder Law in Lake Oswego, we help families throughout Oregon with wills, trusts, and long-term care planning. We work on a flat-fee basis, so you know the cost up front. We will listen to what matters to you, ask the questions an AI tool will not, and make sure your plan is signed, funded, and ready to work when your family needs it. Contact us to schedule a consultation.

This post is general information, not legal advice. Every family's situation is different.