
Challenging a will is never easy. The person bringing the claim is usually grieving while also questioning whether the document reflects what their loved one actually wanted. Sometimes a will contains provisions that feel completely out of character. In other situations, mental decline, outside pressure, or suspicious timing raises serious concerns about how the will was created.
Will contests are formal legal actions with strict deadlines and high emotional and financial stakes. When legitimate questions exist, understanding your rights and acting quickly is essential. Buckman, Buckman & Castellano, P.A., represents clients in will contest matters throughout Sarasota and Florida, helping families determine whether a challenge is appropriate and advocating when litigation becomes necessary.
What Is a Will Contest?
A will contest is a legal challenge to the validity of a will or specific provisions within it. The person bringing the challenge asks the probate court to determine that the will does not reflect the deceased person’s true intent and should not be enforced as written.
If a contest succeeds, the court may invalidate the entire will, allowing a prior will to control if one exists. In other cases, only certain provisions may be set aside while the remainder of the will stands.
Because these disputes often involve close family members, the legal process can be emotionally taxing and permanently strain relationships. For that reason, will contests must be grounded in valid legal principles, not dissatisfaction alone.
Legal Grounds for Contesting a Will
Florida law does not allow a will to be challenged simply because it feels unfair. A valid contest must rest on recognized legal grounds.
Lack of Testamentary Capacity
To create a valid will, the testator must understand three basic things at the time of signing: the nature of their assets, who their natural beneficiaries are, and what it means to sign the document.
Florida’s capacity standard is relatively low. Advanced age alone does not invalidate a will, and even individuals with medical conditions such as dementia may have lucid periods during which they possess sufficient capacity. The focus is on the testator’s mental state at the specific moment the will was executed. (For deeper detail on this ground, see the lack of capacity.)
Evidence may include medical records, physician testimony, attorney notes, witness statements, and communications from the relevant period. For a deeper discussion, see the page on capacity constraints.
Undue Influence
Undue influence occurs when someone exerts pressure so severe that the testator’s free will is replaced by another person’s desires. This goes beyond persuasion and involves domination or control.
Courts examine factors such as the existence of a confidential relationship, the influencer’s involvement in preparing or procuring the will, unnatural or unexpected provisions that benefit the influencer, and whether the testator was particularly vulnerable due to illness, dependency, or isolation.
Because undue influence often happens privately, these cases usually rely on patterns: who had access, who handled appointments, who controlled communication, and who gained from the change.
Fraud
Fraud involves deception that affects the will. It may involve tricking someone into signing a document they did not understand, misrepresenting what the document said, or using false information to cause the testator to include or exclude someone.
A successful fraud claim generally requires proof that the deception was intentional and that the testator relied on it when making the estate decision.
Improper Execution
Florida law requires strict formalities for executing a valid will. The testator must sign the will in the presence of at least two witnesses, who must then sign in the testator’s presence and in each other’s presence.
Failure to follow these requirements, even unintentionally, can invalidate an otherwise legitimate will.

The Three-Month Deadline
Florida law imposes a strict three-month deadline for filing will contests. The clock starts when you receive the Notice of Administration.
This compressed timeline requires immediate action if you have concerns. You can’t wait to see how estate administration unfolds, or try to resolve issues informally for months. Once those three months pass, you lose the right to contest the will regardless of how strong your grounds might be.
If you have any concerns about a will’s validity, consult an attorney immediately upon receiving the Notice of Administration.
The Will Contest Process
Filing a will contest starts with a petition to the probate court. You lay out your grounds for challenging the will and ask the court to reject it or revoke its admission to probate.
The parties then enter discovery, where evidence is gathered through medical records, financial documents, depositions, and witness testimony. Outside professionals often play a central role. Medical practitioners may address mental capacity, while other professionals explain manipulation or undue influence dynamics.
Settlement discussions happen in most cases. The expense of taking a will contest to trial, combined with the uncertainty about how a judge or jury will decide, motivates parties to explore compromise. Sometimes a modified distribution satisfies everyone better than rolling the dice at trial.
If negotiations break down, the case goes to trial. The burden of proof rests on the person challenging the will, who must establish that the document is invalid under Florida law.
Costs and Risks of Will Contests
Will contests drain bank accounts fast. Between attorney fees for discovery work, professional witness costs, court filings, and trial preparation, you can easily spend tens of thousands of dollars on a complex case.
You typically pay your own attorney fees as the case progresses, though you may recover them from the estate if you prevail on grounds that benefit all beneficiaries.
There’s also the risk of losing. If the court upholds the will, you receive only what the will provides. You’ve burned through money on legal fees, fractured family relationships that may never heal, and held up estate administration for months or years, all without changing what you’ll actually receive.
An additional risk: some wills include “no contest” clauses that disinherit anyone who unsuccessfully challenges the will. Florida law enforces these clauses, though exceptions do exist when the contestant has probable cause.
Before filing a will contest, have an honest conversation with your attorney about the likelihood of success, the potential costs, and what you stand to gain.

When You Should Consider a Will Contest
A will contest may warrant serious consideration when:
- A will contains dramatic, unexplained changes from prior estate plans
- The testator experienced a significant cognitive decline around execution
- A person in a position of trust receives unusually large benefits
- The will was signed during illness, hospitalization, or heavy medication
- Evidence suggests manipulation, pressure, or deception
Each situation requires careful legal analysis. Will contests often connect to the broader probate litigation work we handle.
How We Handle Will Contest Cases
At Buckman, Buckman & Castellano, P.A., Allie Castellano approaches contests with both legal rigor and sensitivity to family dynamics. We begin with an honest assessment of whether there are legal grounds and whether pursuing a contest makes practical sense.
When a case is viable, we conduct thorough investigations, gather supporting evidence, consult outside professionals, and pursue resolution through negotiation when appropriate. If litigation becomes necessary, we prepare every case as though it will be tried.
If you’ve received a Notice of Administration and have concerns about the will’s validity, don’t wait. The three-month deadline is absolute.
Contact Buckman, Buckman & Castellano, P.A. immediately to discuss your concerns. We’ll review the circumstances, explain your legal options, and help you make an informed decision.