Jill M. Santiago Law Offices

Estate Planning Attorney in Rhode Island & Massachusetts

(401) 307-5556
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Why You Shouldn’t Use AI To Write Your Estate Plan

December 22, 2025 by Jill Santiago

A courtroom is a fantastic place for a lawyer to get a real education. I’m telling you, probate court is like a masterclass in “What Not to Do” when it comes to estate planning. I see all sorts of things, but the common theme is always the same: a badly-written plan leaves a massive, expensive mess for a family to clean up.

 

The Estate Planning Mistake One Client Of Mine Made Recently

One guy, bless his heart, used one of those self-help legal websites to whip up his will. He must have been having an off day because he somehow managed to name himself as his own executor! That’s right, he put himself in charge of handling his estate… from the afterlife. Apparently, his son did not bother to read the will, as he presented it to the court with the impression that he was the executor. That was one confused judge! The will was also not signed properly, and in the end, the court rejected it.

I could probably jot down 100 reasons why trusting your life savings and family’s future to artificial intelligence is a bad idea, but let’s just stick to the main point: These are serious legal documents with serious, real-world consequences.

For example, do you know the difference between per stirpes and per capita? If your answer is “Sounds like something from a fancy Italian restaurant,” then you absolutely need an attorney. These are not fill-in-the-blank puzzles.

 

Automated Legal Documents Aren’t New

Now, automated legal documents aren’t new. For decades, you could log on to a website, fill in a few boxes, and poof! Out pops a contract or a will. Sounds easy, right? Not so fast, my friend.

The whole process of planning your estate is full of legal landmines that most people don’t even know exist. A seasoned estate planning attorney is like a detective. We dig deeper and ask those awkward, slightly nosey questions to make sure your plan actually meets your goals, not just whatever the computer form asks for.

The newest generation of AI, like ChatGPT, is even more casual. You just politely ask it to “draft a will,” give it a few names, and it spits something out. But here’s the kicker:

ChatGPT can’t give legal advice. It just rearranges words. 

Artificial intelligence doesn’t care. It won’t ask the vital follow-up questions to uncover the elephant-in-the-room concern you didn’t even realize you had.

 

 

A Human Can Read The Room, Which An “AI” Bot Could Never Do

This brings me to the messy, human side of planning. Attorneys are just people with families and feelings. Experienced estate planning attorneys are especially good at reading the room. We pick up on your body language and tone, all the stuff you don’t say, to truly understand your worries and give you the best legal guidance. After all, a robot can’t offer you a comforting tissue or understand the quiet sigh when you talk about Uncle Frank.

 

Avoid Legal Landmines, Have A Real Experienced Estate Planning Attorney In Rhode Island Help You Today

Whether you stumbled across this blog post while searching for an easy way to draft your estate plan, or you currently have a will that you put together yourself or with the help of AI, you’re in the right place.  Resist the Robots!  Book a call with me and I’ll help you avoid tough lessons that come from experiencing probate court, saving you time and money!

(401) 307-5556

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In Death, Taxes & Change, estate planning attorney Jill M. Santiago guides you through the complex (and often overwhelming) world of wills, trusts, and future planning—with clarity, compassion, and zero legal jargon. Whether you are a Rhode Island resident, a snowbird with property in multiple states, or someone with loved ones who have special needs, this book equips you to create a plan that reflects your values and avoids unnecessary court battles.

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Filed Under: DIY, Probate

Address: 2348 Post Rd Suite 106, Warwick, RI 02886 | Phone: (401) 307-5556 | Email: info@jmslawltd.com

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