Post-Execution Conduct Can Create a Triable Issue of Confidential Relationship in Will Contests: Matter of Dibble

Court: Appellate Division, Third Department (New York)

Date: November 6, 2025

Citation: 2025 NY Slip Op 06109 (Matter of Dibble)

Introduction

Matter of Dibble is a contested probate appeal that refines New York’s approach to undue influence challenges where close family members step into fiduciary or quasi-fiduciary roles around the time of a will’s execution. The Third Department affirmed an order that dismissed a fraud objection but permitted an undue influence objection to proceed to trial based on evidence suggesting a potential confidential relationship between the decedent and the will’s beneficiaries—his grandchildren—who also wielded a power of attorney and assisted with his affairs.

The decision is important for two reasons. First, it underscores that post-execution conduct—such as later transactions under a power of attorney and adult protective services (PSA) findings—may be considered, together with contemporaneous facts, to support an inference that a confidential relationship existed at the time of execution. Second, it reiterates the high particularity required to sustain a fraud objection, especially where the alleged misstatements occur after the will’s execution.

The parties are the decedent’s grandchildren, Courtney R. Howell and Nathan A. DeStephen (petitioners and proponents of probate), and the decedent’s son, Gregory F. Dibble (objectant). After the decedent’s spouse died in June 2017, the decedent executed a new will leaving his entire estate to the petitioners, in contrast to a February 2017 will that would have left his estate to his son if his wife predeceased him. The son objected, alleging undue influence and fraud. The Surrogate’s Court dismissed the fraud objection but found triable issues on undue influence and confidential relationship. Both sides appealed; the Third Department affirmed.

Summary of the Opinion

The Third Department held:

Summary judgment for the petitioners on the undue influence objection was properly denied. Although the petitioners established prima facie entitlement to probate via proof of due execution (including affidavits from the drafting attorney and a witness), the respondent raised a triable issue of fact that a confidential relationship may have existed—potentially triggering burden shifting at trial if proved.
The record supporting a triable issue included: the decedent’s progressive dementia since approximately 2014; the wife’s prior management of finances; petitioners’ assumption of financial and life-management responsibilities after the wife’s death; the petitioners’ role in arranging the will appointment; the contemporaneous execution of a power of attorney in their favor; and subsequent PSA findings and large transactions by petitioners under the power of attorney suggesting the decedent’s confusion and petitioners’ control.
The fraud objection was properly dismissed because the objectant’s allegations were speculative, lacked the required specificity, and in any event related to statements made after execution of the contested will—too late to have induced the testamentary disposition.
The Surrogate’s denial of discovery sanctions was a provident exercise of discretion given ongoing litigation and the court’s ability to impose sanctions later if warranted.

Detailed Analysis

Precedents Cited and Their Influence

Matter of Ostrander, 237 AD3d 1444 (3d Dept 2025): Cited for two pillars: summary judgment standards in probate contests and the presumption of regularity arising from proof of proper execution via attorney/witness affidavits. Here, those materials shifted the burden to the objectant to raise triable issues on undue influence or fraud. Ostrander also frames when summary judgment can be appropriate notwithstanding the generally fact-intensive nature of undue influence claims.
Matter of Timer, 221 AD3d 1103 (3d Dept 2023) and Matter of Stafford, 111 AD3d 1216 (3d Dept 2013), lv denied 23 NY3d 904 (2014): Reaffirm the classic undue influence elements—motive, opportunity, and the actual exercise of undue influence. These cases inform the analytical structure the court applied in weighing the record for triable issues.
Matter of Linich, 213 AD3d 1 (3d Dept 2023): Twofold relevance. First, it clarifies that the objectant must show conduct so pervasive that the will reflects the influencer’s volition rather than the decedent’s. Second, on fraud, Linich underscores the need for particularized allegations—times, dates, places—which the respondent here failed to supply.
Matter of Mary, 202 AD3d 1418 (3d Dept 2022) and Dwyer v Valachovic, 137 AD3d 1369 (3d Dept 2016): Establish burden shifting where a confidential relationship exists: the beneficiary must prove by clear and convincing evidence that the benefit was not the product of undue influence. Matter of Mary also recognizes the tension between familial ties (which may negate presumptions) and circumstances suggesting “cupidity.”
Matter of Giaquinto, 164 AD3d 1527 (3d Dept 2018), affd 32 NY3d 1180 (2019): Defines a confidential relationship as one involving unequal terms due to weakness, dependence, or justified trust making unfair advantage probable. This definition underpins the court’s triable-issue finding.
Matter of Rozof, 219 AD3d 1428 (2d Dept 2023) and Fischer v Reed, 224 AD3d 886 (2d Dept 2024): Emphasize that whether a confidential relationship exists is ordinarily a question of fact—supporting the Third Department’s reluctance to resolve the issue on summary judgment here.
Matter of Dralle, 192 AD3d 1239 (3d Dept 2021) and Matter of Cameron, 126 AD3d 1167 (3d Dept 2015): Additional affirmations of the presumption of regularity and the shifting burden to the objectant once due execution is shown.
Matter of Antoinette, 238 AD2d 762 (3d Dept 1997): Teaches that no single factor is dispositive; a “confluence of many factors” can support undue influence. It also cautions that close family ties may negate presumptions but not where facts support an inference of self-interest (“cupidity”).
Matter of Prevratil, 121 AD3d 137 (3d Dept 2014), Matter of Nealon, 104 AD3d 1088 (3d Dept 2013), affd 22 NY3d 1045 (2014), and Matter of Ruhle, 173 AD3d 1389 (3d Dept 2019): Comparative authorities on when summary judgment is or is not appropriate in the face of potential confidential relationships and undue influence claims.
Matter of Urban, 222 AD3d 1088 (3d Dept 2023) and Matter of Christie, 170 AD3d 718 (2d Dept 2019), along with Matter of Robbins, 206 AD3d 739 (2d Dept 2022), Matter of Martinico, 177 AD3d 882 (2d Dept 2019), Matter of Mele, 113 AD3d 858 (2d Dept 2014), Matter of Paigo, 53 AD3d 836 (3d Dept 2008), and Matter of Bianco, 195 AD2d 457 (2d Dept 1993): Collectively define the stringent requirements for pleading and proving fraud in a will contest—especially the necessity of a knowingly false statement that actually induced the testamentary disposition. Statements made after execution cannot, as a matter of law, have induced the execution.
Matter of Spiak, 208 AD3d 1482 (3d Dept 2022), Castillo v Charles, 210 AD3d 625 (2d Dept 2022), and Matter of Scaccia, 66 AD3d 1247 (3d Dept 2009): Guide the court’s discretionary approach to discovery sanctions, counseling restraint and measured responses while preserving the court’s ability to sanction later if noncompliance persists.

Legal Reasoning

The court’s analysis proceeded in three steps: the prima facie case for probate; the undue influence/confidential relationship objection; and the fraud objection.

1) Prima facie case and presumption of regularity. Petitioners met their initial burden by submitting the will and affidavits from the drafting attorney and a witness, establishing due execution and invoking the presumption of regularity. This shifted the burden to the objectant to raise a genuine dispute on undue influence or fraud.

2) Undue influence and confidential relationship. The objectant pointed to a record that, taken in the light most favorable to him at the summary judgment stage, supported an inference that the petitioners were in a position of dominance or trust over the decedent at the time the will was made:

Decedent’s progressive dementia since approximately 2014 with worsening symptoms.
Decedent’s spouse (who had managed finances and life activities) died in June 2017, just ten days before the challenged will, creating a period of heightened vulnerability.
Protective Services for Adults notes (June 21, 2017) reflecting that petitioners assumed responsibility for finances and life management immediately after the spouse’s death; one petitioner had long resided with and supported the decedent.
Petitioners’ involvement in arranging the attorney appointment when the decedent raised changing his will.
The new will’s marked deviation from the February 2017 will, which would have left the estate to the son if the spouse predeceased him; notably, the February will expressly disinherited the petitioners’ parents.
Execution of a power of attorney in favor of the petitioners on the same day as the new will, followed by large transactions, petitioners’ signatures on checks of unclear purpose, and PSA documentation indicating the decedent’s confusion regarding certain transactions.

Two features of the court’s reasoning are especially instructive:

Temporal scope of evidence: Although many of the questionable financial transactions occurred after the will’s execution, the court expressly held they could be considered alongside contemporaneous circumstances to support an inference that a confidential relationship existed when the will was executed. This is a pragmatic evidentiary approach recognizing that dominance, dependence, and patterns of control often straddle the execution date.
Family ties versus “cupidity”: While close family relationships can dilute presumptions of undue influence, they do not immunize suspicious circumstances. Here, viewed favorably to the objectant, the confluence of factors could support a finding that petitioners acted from self-interest rather than familial duty—an issue for the factfinder, not resolution on papers.

Because the existence of a confidential relationship is ordinarily a fact question, and because establishing such a relationship could shift the burden at trial to petitioners to rebut undue influence by clear and convincing evidence, summary judgment was inappropriate on the undue influence objection.

3) Fraud objection. In contrast, the fraud claim failed as a matter of law. The objectant’s key allegations—that petitioners accused him of financial exploitation and allegedly told a treating physician similar things—were speculative, not particularized, and, most importantly, occurred after the will was executed. Even if made, such statements could not have induced the decedent to execute the will and therefore could not sustain a fraud objection. Dismissal on summary judgment was thus proper.

4) Discovery sanctions. The court declined the drastic remedy of dismissal as a discovery sanction, noting that while compliance concerns existed, litigation was ongoing and lesser sanctions remained available should noncompliance persist. This reflects the measured, discretionary approach typical in Surrogate’s Court practice.

Impact and Practical Implications

Use of post-execution conduct: Litigants can now cite Dibble for the proposition that post-execution power-of-attorney conduct and PSA findings may be used, in combination with contemporaneous facts, to create a triable issue of a confidential relationship existing at the time of execution. This is particularly salient in caregiving or fiduciary-family situations.
Caregiver-beneficiary scrutiny: Family members who assume control over finances and life activities and then benefit under a will executed in proximity to that assumption should expect heightened judicial scrutiny and a possible burden shift at trial if a confidential relationship is established.
Estate planning practice: Attorneys should carefully document the testator’s independence, capacity, and voluntariness, especially when beneficiaries are involved in scheduling, transportation, or communications. Consider separate meetings with the testator, explicit inquiry into recent changes, and detailed notes addressing susceptibility and potential influencers.
Objectants’ roadmap: To defeat summary judgment on undue influence, assemble a holistic record—health vulnerabilities, timing (e.g., immediately post-bereavement), beneficiary involvement in the willmaking process, fiduciary appointments (POA), and subsequent control over finances. The “confluence of factors” approach is decisive.
Fraud objections: These remain difficult to sustain. Particularity is essential; the misrepresentation must be both knowingly false and causally linked to the execution. Statements made after execution will not suffice.
Discovery management: Courts are unlikely to dismiss objections for discovery issues early; parties should pursue incremental remedies and build a record for sanctions if noncompliance persists.

Complex Concepts Simplified

Presumption of regularity: When a will appears properly executed and attesting witnesses or the drafting attorney provide affidavits, the law presumes it was duly executed. The objectant must then present evidence raising genuine issues (e.g., undue influence).
Undue influence: Requires proof of motive (a reason to influence), opportunity (access and ability), and actual exercise (conduct that overcame the testator’s free will so the will reflects the influencer’s wishes).
Confidential relationship: A relationship where one party’s weakness or dependence gives the other a position of dominance or trust, making unfair advantage probable. If proven, the burden may shift to the beneficiary to prove, by clear and convincing evidence, the transaction was free of undue influence.
Burden shifting: Normally the objectant must prove undue influence. But if a confidential relationship is shown, the beneficiary must disprove undue influence with clear and convincing evidence.
Prima facie case: The minimum showing needed to require a response. In probate, due-execution proof typically satisfies this, shifting the need to respond to the objectant.
Summary judgment: A paper-based decision without trial when no material facts are disputed. It is “rare” in will contests, especially on undue influence, due to fact-intensive inquiries into relationships and motivation.
Fraud in probate: Requires a knowingly false statement that actually induced the testator to execute the will differently. Vague, speculative, or post-execution statements cannot establish causation.
PSA (Protective Services for Adults): A New York agency that intervenes to protect vulnerable adults. Its notes and investigations can provide evidentiary context on vulnerability, dependence, and fiduciary control.
Sanctions for discovery violations: Penalties for failing to comply with disclosure obligations. Dismissal is a drastic remedy, usually reserved for willful and contumacious conduct after lesser remedies fail.

Conclusion

Matter of Dibble affirms familiar probate principles while making a meaningful evidentiary clarification: post-execution fiduciary conduct and protective-services findings may be considered—together with surrounding circumstances—to create a triable issue of a confidential relationship at the time a will was executed. This nuance is pivotal in modern will contests involving family caregivers who also hold powers of attorney or manage a decedent’s affairs.

The decision simultaneously provides a cautionary tale for practitioners and fiduciary-beneficiaries: close family ties do not inoculate against undue influence claims where the “confluence of factors” suggests dominance and self-interest. Conversely, it reinforces the high bar for fraud objections, requiring specific, causative misrepresentations tied to execution. Finally, it reflects the judiciary’s restrained approach to discovery sanctions while preserving flexibility to impose them later.

In sum, Dibble will likely be cited for (1) the permissibility of using post-execution conduct to infer a pre-existing confidential relationship sufficient to defeat summary judgment; (2) the continued vitality of burden shifting in confidential-relationship undue influence cases; and (3) the stringent pleading and proof requirements for fraud in probate. It is a practical, fact-sensitive decision with significant implications for estate litigation and planning in New York.