The estate plans that go to court are almost never the ones drafted carelessly from scratch. They’re the ones that were solid when they were signed, then quietly fell out of date over the next fifteen or twenty years while life kept moving. A second marriage, a grandchild, a sold business, a brokerage account opened on a whim. At Roven Law Group, the contested estate matters that come through the door usually trace back to a small handful of mistakes that were easy to fix when the client was alive and impossible to fix after they were gone. The patterns are consistent enough that anyone in their 50s or 60s reviewing their plan can use them as a checklist.
Here are the mistakes that fuel the most family disputes in New York, with what a thoughtful plan does instead.
Beneficiary Designations That Don’t Match the Will
This is the most common single error in estate practice, and it costs families more than any other. Retirement accounts, life insurance policies, annuities, and transfer-on-death brokerage accounts pass by beneficiary designation, not by the will. A will that leaves everything to a current spouse is overridden by an old 401(k) designation naming the previous spouse from 1998.
The cases land in court because the family expects the will to control. It doesn’t. The Supreme Court decided this directly in Kennedy v. Plan Administrator for DuPont Savings, 555 U.S. 285 (2009), and New York courts have followed the same logic in case after case. The beneficiary on the account is the beneficiary, regardless of what the will says.
A working review should pull every designation on every account at least every five years, and immediately after:
- Marriage, divorce, or remarriage
- The birth or adoption of a child or grandchild
- The death of a previously named beneficiary
- Rolling a 401(k) into an IRA, which often resets the designation to a default
Unsigned or Improperly Witnessed Amendments
People in their 60s often make handwritten changes to their wills or trusts thinking the intent is what matters. New York has clear formalities under EPTL § 3-2.1 for wills: in writing, signed by the testator at the end, signed in the presence of two attesting witnesses or acknowledged to them, with the testator declaring the document to be a will.
Margin notes don’t count. Crossed-out paragraphs don’t count. A typed addendum stapled to the will without proper execution doesn’t count. Surrogate’s Court will admit the original will and ignore the changes, which often produces a result the decedent specifically didn’t want.
The fix is straightforward. Real changes get made through a codicil to the will or a restatement of the trust, both executed with the same formalities as the original. Anything else creates a paper trail of intent without the legal effect to back it up, and that’s the kind of evidence that fuels contested probates.
Naming the Wrong Executor or Trustee
The choice of executor is often made for emotional reasons. The oldest child. The closest sibling. The friend who handled everything when the spouse died. These choices feel obvious when the will is being signed and become disasters when the estate is being administered.
The questions that should actually drive the decision:
- Does this person live close enough to handle the practical work, like meeting with the attorney, sorting through the apartment, and appearing in Surrogate’s Court when needed?
- Are they organized enough to keep records, file tax returns, and account to beneficiaries?
- Can they remain neutral toward the other beneficiaries, particularly siblings who don’t get along?
- Are they young enough and healthy enough to actually serve when the time comes?
A 78-year-old client naming a 76-year-old sibling as executor is creating a problem that compounds with time. A blended-family client naming one child from the first marriage while the second spouse is still living is setting up a fight before the body is in the ground.
Naming co-executors who don’t get along is its own category of mistake. Two children who haven’t spoken in five years won’t suddenly cooperate to administer the estate. The will should either name a single executor with a successor, or name a neutral professional fiduciary where family dynamics make that the better call.
Leaving Assets Outright to Minors
A will that leaves money “to my grandchildren equally” without further provision is a will that creates a court proceeding. Minors can’t take legal title to assets in their own name in New York. Without a trust or a custodial arrangement, the inheritance goes into a court-supervised guardianship under SCPA Article 17, with annual accountings, court approval for major decisions, and an outright distribution at age 18.
Eighteen-year-olds inheriting six figures rarely make decisions their grandparents would have endorsed. A 2024 inheritance handed to a college freshman doesn’t get spent the way most testators would want.
The fix is a trust for each minor beneficiary, typically held until ages that match the testator’s actual judgment about maturity. Common structures distribute one-third at 25, one-third at 30, and the balance at 35. Health, education, maintenance, and support distributions are available from the trustee in the meantime. Uniform Transfers to Minors Act accounts under EPTL Article 7-A can work for smaller amounts, with the assets transferring outright at 21.
Failing to Update After Divorce, Death, or Remarriage
New York’s EPTL § 5-1.4 automatically revokes will provisions in favor of a former spouse upon divorce, but only for the will itself. Beneficiary designations on retirement accounts, transfer-on-death registrations, and life insurance are not automatically revoked, and trust provisions naming the former spouse as trustee or beneficiary aren’t either.
The pattern Roven Law Group sees repeatedly: a client divorces in 2010, dies in 2024, and the IRA beneficiary form from 2002 still names the ex-spouse. The ex-spouse inherits the IRA. The current family contests, the litigation runs for two years, and the ex-spouse wins.
Hiding the Plan Until the Reading of the Will
The “reading of the will” is mostly a movie device. In real life, families that hear about the plan for the first time at the funeral often end up litigating it. Surprise breeds suspicion, and suspicion breeds will contests.
Clients in their 50s and 60s who care about family peace should consider:
- Telling the executor where the original documents are kept and what’s expected of them
- Letting adult children know in general terms what’s in the plan, especially when the distribution is uneven for legitimate reasons
- Documenting the reasons for any unusual choices in a separate letter of explanation, which won’t override the will but provides context that defeats undue influence claims
How Roven Law Group Approaches Estate Updates
A good estate plan is not a one-time document. It’s a working set of instructions that needs to be reviewed when life changes and refreshed as the law shifts. Janice G. Roven has been preparing and updating wills and trusts for New York families for more than 35 years, including blended-family plans, business succession arrangements, and credit shelter planning tied to the New York estate tax exemption. The firm also handles will contests and contested estate administration in Surrogate’s Court when the planning didn’t get done in time.
For readers who want the underlying authority, EPTL § 3-2.1 covers will formalities, EPTL § 5-1.4 covers automatic revocation on divorce, and the New York County Surrogate’s Court publishes procedural guides at nycourts.gov.
The Bottom Line
Most estate fights are preventable, and the prevention almost always lives in a 60-minute review every few years rather than in some elaborate legal document. To talk through whether your current plan still works for your family and what should be updated, schedule a consultation with Roven Law Group.
