I’m an estate planning attorney, and this is a story about how I saved two PhDs who used online wills from accidentally disinheriting each other.
They thought they were being clever by using an online will. Instead, they created a legal mess that could have cost their family everything. Their DIY documents eventually ended up in my shredder—not because they were careless people, but because they trusted a system that gave them a false sense of security.
And their story explains why I regularly tell people that an online will can sometimes be worse than having no will at all.
The Moment I Know There’s a Problem
At least once a week, someone walks into my office, proud of themselves, and drops a stack of papers on my desk.
“I did my will online,” they’ll say. “Saved a ton of money. Can you just give it a quick look?”
They feel relieved. They checked a major item off their to-do list. The documents look official. The process felt easy.
And far too often, I have to give them bad news.
The document they spent hours creating—the one they’re trusting to protect their family—isn’t going to work the way they think it will. Sometimes it’s flawed. Sometimes it’s ambiguous. And sometimes it’s invalid from the start.
The convenience is tempting. A few clicks, a credit card payment, and you feel like you’ve handled something important. But that feeling of security can be an illusion.
No one illustrates this better than my two PhD clients.
The “Smart Person” Problem
A married couple came to see me several years after creating their wills online. Both were brilliant—PhDs in highly technical fields. Analytical, detail-oriented, and careful. They had researched their options and believed they had done everything correctly.
They used a popular online platform, answered every question carefully, printed the documents, signed them, and had witnesses present. From their perspective, the job was done.
A friend eventually convinced them to have the documents reviewed “just in case.” That’s how they ended up in my office.
As I read through the wills, I felt that sinking feeling estate planning attorneys know well. The documents looked fine on the surface. But legally, they were a disaster.
The first problem was execution. They had witnessed each other’s wills. In many states, a beneficiary should not serve as a witness. By signing for each other, they had potentially invalidated both documents from the beginning.
But it didn’t stop there.
The template language was generic and clumsy. The online questionnaire never asked the right follow-up questions about their actual goals. As a result, the documents named distant relatives as executors instead of each other. If one spouse died, the survivor could have been forced to work with a cousin managing the estate instead of remaining in control.
Then came the most serious issue. Because of the ambiguous template language, a real legal argument could be made that they had accidentally disinherited each other. Their assets could have bypassed the surviving spouse entirely.
These were not careless people. They were experts in their own fields.
But being intelligent doesn’t make someone an expert in estate law. I see this constantly. Online platforms cannot ask nuanced questions or recognize when an answer creates unintended consequences. They provide structure, but not judgment.
That’s the “smart person problem.” The process feels thorough, so people assume the result must be correct.
The Most Common Ways Online Wills Fail
The story sounds dramatic, but it’s not unusual. The same categories of problems show up again and again.
The first category is execution failures. This simply means the will wasn’t signed correctly under state law. The rules are strict. Some states require two witnesses, some three. Some have rules about who can serve as a witness. Some have specific notarization requirements.
An online template doesn’t know who is actually in the room when you sign. It can’t stop a beneficiary from acting as a witness. It can’t correct a missing date or an incomplete signature. And a technical mistake can invalidate the entire document.
The second category is more dangerous: substantive content problems. This is where the words in the will don’t actually do what the person believes they do.
Families are rarely simple. Blended families, minor children, special needs beneficiaries, and uneven inheritances all require careful drafting. A generic template cannot anticipate these issues.
A basic will might accidentally disinherit step-children. It might create an inheritance that causes a disabled beneficiary to lose government benefits. It might conflict with beneficiary designations on retirement accounts or life insurance. It might ignore how property is titled altogether.
And increasingly, online wills fail to address digital assets—online accounts, cryptocurrency, and digital records that families struggle to access after death.
The result is confusion, delay, and often expensive court involvement.
The Myth That “Something Is Better Than Nothing”
One of the most common arguments I hear is this: “Isn’t a flawed will still better than no will?”
In practice, often the answer is no.
If someone dies without a will, state intestacy laws apply. These are default rules based on family relationships. They may not be ideal, but they are predictable.
A flawed or ambiguous will creates uncertainty. One family member believes the document is valid. Another challenges it. The estate becomes a legal dispute instead of a clear process. Families end up hiring lawyers and spending large portions of the inheritance fighting over interpretation.
The money saved on the front end disappears quickly in legal fees on the back end.
Worse, DIY online wills create a false sense of completion. People stop revisiting their plan because they believe the work is done. They never see the failure themselves. Their family does.
I’ve seen families torn apart over a single ambiguous sentence in a will that was downloaded for less than the cost of dinner.
And if you read the disclaimers on most online platforms, they are clear about one thing: they are not law firms, and they are not providing legal advice. If the document fails, they accept no responsibility for the outcome.
What Happened to the PhD Clients
In the end, we threw those online wills away and started over.
We talked through their goals, their family dynamics, and the real risks they hadn’t considered. What if both spouses died at the same time? Who would care for minor children? How should inheritances be managed? Should assets pass outright, or be protected in trust?
We built a plan that actually reflected their intentions. It was legally sound, coordinated with their assets, and designed to work in the real world—not just look good on paper.
Yes, it cost more than an online wills template version. But what they purchased wasn’t a document. They purchased certainty and peace of mind.
The Reality About Online Wills
The truth is simple: you don’t know what you don’t know.
An online form cannot give legal advice. It cannot recognize risks unique to your situation. And it cannot replace the judgment of someone who has seen hundreds of estate plans succeed—or fail—after someone passes away.
Your family’s future is too important to leave to a template.
If this story made you reconsider how your own plan is set up, the next step is education. Before you sign anything, make sure you understand your options and how estate planning actually works.
You can start by taking my free course at: www.FreeTrustCourse.com . It walks through the basics in plain English so you can make informed decisions and avoid the kinds of mistakes that turn a simple plan into an expensive problem later.