Financial PlanningEstate PlanningContesting a Will: A Planner's No-BS Guide to Success in 2025

Contesting a Will: A Planner’s No-BS Guide to Success in 2025

Success Rate of Contesting a Will

When a loved one’s will feels like a betrayal of their true wishes, the sense of injustice is overwhelming. Challenging that will in court seems like the only path to setting things right.

As a financial planner for almost three decades, I’ve seen these battles over estate documents up close. They are wars of attrition, fought with money, time, and emotional fortitude.

Before you spend a single dollar on an attorney, you must conduct a brutally honest assessment of your situation.

This guide is not legal advice. It is a strategic framework to help you determine if you have a viable case, understand the real costs, and prepare for the fight ahead.

In This Guide, You’ll Discover:

  • The First Hurdle: Do you even have the legal “standing” to challenge a will in probate court?
  • Beyond “Unfair”: The four specific legal grounds that a court will actually recognize over an estate.
  • The Evidence Checklist: The specific proof, from medical records to witness testimony, you need for claims like undue influence or lack of capacity.
  • The 3-P Viability Protocol™: My proprietary framework for deciding if you should Proceed or Pause with contesting an estate.

Step 1: Do You Have ‘Standing’ to Contest a Will in Court?

Before anything else, you must clear this first legal hurdle. You can’t contest a will just because you feel it’s unfair. To have legal standing, you must be an “interested party,” meaning you are:

  • A beneficiary named in the current will.
  • A beneficiary named in a previous version of the will.
  • A legal heir under state law who would inherit if no will existed.

If you don’t fit into one of these categories, the court will likely dismiss your case.


Step 2: The 4 Valid Grounds for a Will Contest

Last Will and Testament
Last Will and Testament

Your challenge must be built on one of these four pillars. Your feelings, while valid, are not a legal argument.

1. Lack of Testamentary Capacity

This argues the testator (the person who made the will) was not of “sound mind” when signing. You must prove they didn’t understand what they owned, who their family was, or what the document did.

  • Evidence Needed: Medical records showing cognitive decline (dementia, etc.), pharmacy logs of psychoactive drugs, and testimony from witnesses (nurses, neighbors) who observed confusion.

2. Undue Influence

contesting a will
contesting a will

I worked with a client, James, in late 2023, whose father left his entire multi-million dollar estate to a caregiver he’d known for only six months.

Contrarian insight:
The “smoking gun” in these cases is rarely a single, witnessed act of aggression; it’s a subtle, documented pattern of isolation and dependency. We focused on proving the caregiver systematically cut off communication with family and took the father to a new lawyer she had chosen.

The legal term for this level of involvement is often procurement,” and it’s a massive red flag for probate courts. Was the new will an act of love, or an act of capture?

3. Fraud or Forgery

This means the will is a product of active deception. Either the testator was tricked into signing it (fraud), or the signature is faked (forgery). This claim often requires costly handwriting expert analysis.

4. Improper Execution

Every state has strict signing and witnessing rules. According to the American Bar Association (ABA), a will must typically be in writing, signed by the testator, and witnessed by two non-beneficiaries. If these technicalities were bungled, the will can be thrown out.


Step 3: The Michael Ryan Money 3-P Viability Protocol™ – Your Go/No-Go Decision

Answer these questions with brutal honesty before you proceed.

probate last will and testament

Proof:

Do you have the concrete evidence listed above, or a clear path to get it via legal subpoenas? Suspicions are not evidence. Without proof, you have no case.

Price:

I once advised a family who was “sure” they would win a will contest. A year and $80,000 in legal fees later, the case settled for less than their legal bills, and two siblings stopped speaking entirely.

The most overlooked cost is the ‘discovery’ phase. This is where your lawyer’s retainer vaporizes on expensive, time-consuming depositions, interrogatories, and expert witness fees.

Does the potential inheritance justify the very real cost? Our guide on the cost of a living trust can provide context on legal fees in estate matters.

Peace:

Are you prepared for a battle that will likely destroy family relationships forever? Is your goal to honor your loved one’s true wishes, or to win a family war? Because you will rarely get to do both.


What to Expect When You Proceed

If you move forward, you need a specialized probate litigator, not your family’s estate planner. They will file a petition, and the “discovery” process will begin. Be prepared: the burden of proof is on you to prove the will is invalid.

The court’s default position is to assume the will is valid.

🤔 Michael’s Take: What About a “No-Contest Clause”?

Many people are terrified by a “no-contest clause,” which states that any beneficiary who challenges the will and loses forfeits their inheritance. While this sounds intimidating, you need to know that in many states, including populous ones like Florida, these clauses are **not enforceable if the contest is brought in good faith and with probable cause.** Don’t let a boilerplate legal threat be the only thing that stops you from seeking justice. Discuss this specific clause with your probate litigator, as state laws vary significantly. To protect your own legacy, it’s wise to understand **[how to make a will that cannot be contested](https://michaelryanmoney.com/how-to-make-a-will-that-cannot-be-contested/)** in the first place.

What is lack of testamentary capacity?

Lack of testamentary capacity means that the person who made the will was mentally incompetent at the time the will was signed.

What is fraud or undue influence?

Fraud or undue influence means that the person who made the will was subject to undue influence by someone else, such as a caregiver or family member.

What is duress?

Duress means that the person who made the will was forced to sign it against their will.

What are the requirements for a valid will?

The requirements for a valid will vary by state, but generally the person making the will must be of sound mind and body and must sign the will in the presence of witnesses.

Do I need an experienced probate litigation lawyer to contest a will?

While it is not required, it is strongly recommended that you hire an experienced will

Final Takeaway: A Battle of Head, Not Just Heart

The discovery of an unjust will is a deeply emotional experience. But the decision to contest it must be a cold, calculated one. Your feelings of being wronged are valid, but they are not evidence.

Assess your case with cold calculation, and you will make the right decision for your future.

Disclaimer: This article provides educational information only and is not legal advice. Consult a qualified probate litigator in your state for specific guidance.

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Michael Ryan
Michael Ryanhttps://michaelryanmoney.com/
Michael Ryan, Retired Financial Planner | Founder, MichaelRyanMoney.com With nearly three decades navigating the financial world as a retired financial planner, former licensed advisor, and insurance agency owner, Michael Ryan brings unparalleled real-world experience to his role as a personal finance coach. Founder of MichaelRyanMoney.com, his insights are trusted by millions and regularly featured in global publications like The Wall Street Journal, Forbes, Business Insider, US News & World Report, and Yahoo Finance (See where he's featured). Michael is passionate about democratizing financial literacy, offering clear, actionable advice on everything from budgeting basics to complex retirement strategies. Explore the site to empower your financial future.