Following the post-World War II birth rate explosion in the United States, the “Silent” and “Baby Boomer” generations amassed the largest collection of wealth in human history.[1] Improvements in technology and medicine have increased the life expectancy of those generations and, by 2034, Americans over the age of 65 are expected to outnumber children under 18.[2] As members of these generations age, it has led to an unprecedented transfer of wealth to younger generations known as the “Great Wealth Transfer.” Experts estimate that from 2024-2045, older generations will transfer a total of $84.4 trillion to their heirs and charity organizations.[3] Practitioners in the probate litigation sphere predict a rise in disputes and litigation as this Great Wealth Transfer unfolds.
1. What Causes Probate Litigation? Key Drivers of the Current Stage
Increased life expectancy and the rapid advancements in medical care have diminished the sense of urgency to set up proper estate planning. Without careful forethought, these modern trends combined with the rapid transfer of trillions of dollars are bound to increase probate litigation. It is important that families engage with estate planning attorneys early so that they are prepared to handle the transfer of assets following the passing of a family member.
A. Evolving Family Dynamics
The evolution of family dynamics in the modern era may lead to unique complications and disputes over family estates. With the rise of blended families and the prevalence of multiple marriages, competing claims to estates and conflicting interpretations of a decedent’s intent may arise. “Gray divorces,” or separations occurring later in life, often result in disputes over property division if not properly accounted for in an estate plan. Disputes may also arise over unequal distributions among children of different marriages and unexpected beneficiary changes or gifts of family property or businesses that are not aligned with long-standing expectations.
Under Massachusetts law, when an individual passes without a will, certain default rules apply to the division of their estate among family members. Those rules do not take emotional or financial connection to the decedent into account. Thus, second or former spouses, stepchildren, and children from different marriages may receive less than expected if a decedent dies intestate.[4] Those default rules may also apply when the decedent executed their will before a subsequent marriage took place.[5] Moreover, under Massachusetts law, divorce triggers automatic revocation of bequests to a former spouse.[6] Unfortunately, divided or complex family structures also may lead to claims by family members that representatives or trustees of an estate engaged in self-dealing.[7]
B. Cognitive Decline and Vulnerability
While the updating of estate plans is crucial as families evolve, changes by aging family members may invite challenges related to testamentary capacity and undue influence. The Alzheimer’s Association estimates that about one out of every nine Americans over the age of 65 has clinical Alzheimer’s dementia.[8] Cognition impairments and progressive memory loss can lead to difficulty determining the validity of late-stage estate planning and challenges to the testamentary capacity of decedents. Massachusetts courts evaluate testamentary capacity by examining whether the testator was of sound mind during the time of execution and whether the testator understood the nature, substance, and implications of their estate plan.[9] Sudden or substantial changes benefitting a non-relative caregiver, or isolation from long-time advisors and family may also lead to a will contest under claims of undue influence.[10] If you believe that a family member may have been influenced to make an unnatural disposition, contact a probate litigation attorney immediately.
C. The Fallout of Pandemic Crisis Planning and the Rise of DIY Documents
The panic and anxiety created by the Covid-19 pandemic–along with the prevalence of websites and software promoting “easier” or “cheaper” alternatives for creating wills or trust documents–led to an increase in wills created without an attorney, or “DIY” wills, and hastily executed documents.[11] These instruments created without the assistance of a legal professional may have problems like execution defects, ambiguous dispositive provisions and omitted fiduciary powers, or inadequate incorporation of digital and beneficiary-designated assets.[12] All of these defects or ambiguously drafted terms can lead to future challenges of the will’s validity and disputes over interpretation. Furthermore, if no attorney was used to draft the instrument, there will be no lawyer available to testify as to the testator’s capacity at the time of execution, nor their intention and thought process behind their distributions. What was intended to be a cost-effective alternative may actually create expensive and long-standing probate litigation.[13]
2. Modern Assets, Modern Problems: Why Complexity Breeds Contested Probate
A. The Challenge of Real Estate
A significant portion of Baby Boomer wealth is tied to real estate. While real property has historically been considered a safe and valuable investment, passing these assets on to younger generations presents unique challenges.[14] First, as real estate is an illiquid asset, transferring real estate titles involves requirements that do not exist for cash accounts.[15] Second, real estate is not easily divided among heirs.[16] Third, as with many other personal assets, family members often attach strong sentimental value to real estate, which can create family turmoil.
B. The Digital Asset Dilemma
The rise and prevalence of digital assets may also lead to difficulties with estate planning. Digital assets may be unregulated, and their value may either be hard to determine or may fluctuate drastically. Further complicating the issue of digital assets, Massachusetts has not adopted the Revised Uniform Fiduciary Access to Digital Assets Act (RUFADAA). This means that designated personal representatives or fiduciaries do not have statutory authority to access digital accounts from custodians such as Google or other such entities. Furthermore, these custodians may include terms in their service agreements which dictate non-transferability or termination-upon-death, further complicating the transfer of digital assets upon the passing of a testator.
3. Structuring the Plan: How Can Families Proactively Mitigate Risk?
A. Leveraging Trusts
Individuals often use revocable living trusts as mechanisms to keep estate administration private. These trust instruments allow the trustee to manage and distribute trust-titled assets outside of a court-supervised probate proceeding. This avoids the kinds of public disclosures in probate which may lead to further disputes or complications. Filings in a decedent’s probate estate–including petitions, inventories, accounts, and court filings in probate disputes–become part of the public record and are accessible to the general public. In Massachusetts, with the exception of certain trust-related documents recorded or filed to transfer or confirm title to specific assets, trust administration itself is not routinely filed with the Probate and Family Court unless an issue arises or the will is challenged.
B. Clear Communication and Strategic Drafting
Probate litigators sometimes refer to will contests and disputes over probate administration as “sandbox cases.” This term refers to the unfortunate but often seen pattern of lawsuits between siblings or family members which may be triggered by an estate administration issue but are founded in long-standing conflicts between the parties which date back to childhood. A fight in the sandbox may lead to a fight in the courtroom twenty years later over a family member’s estate. Accordingly, while having conversations with beneficiaries may be uncomfortable, it may prevent expensive disputes regarding a testator’s intent after their passing.
Strategic drafting may also prevent future disputes. Massachusetts allows for the inclusion of no-contest clauses in will or trust instruments, limiting a claimant’s ability to challenge the documents. Under a typical no-contest or in terrorem clauses, a beneficiary will forfeit their interest if they contest a will or trust instrument. Courts in the Commonwealth will generally enforce no-contest provisions[17] but allow exceptions for certain circumstances.
C. Securing Your Legacy
As the Great Wealth Transfer unfolds and the “Silent” and “Baby Boomer” generations transfer their wealth, a corresponding rise in probate litigation is expected. While “sandbox disputes” are often inevitable, individuals can limit the possibility of future litigation with a proactive approach to estate planning. The estate planning attorneys at Conn Kavanaugh have experience in drafting will and trust instruments to avoid future disputes . If things have already gone awry, the probate litigation team is experienced in resolving those disputes.
[1] See Guy M. Burns, Scott C. Ilgenfritz, Jonathan S. Coleman, Be Alert for Financial Exploitation of the Elderly, 91 Fla. B.J. 37 (2017).
[2] See U.S. Census Bur., Press Release: Population Projections (2018), https://www.census.gov/newsroom/press-releases/2018/cb18-41-population-projections.html (accessed Aug. 12, 2026).
[3] See Cerulli Associates, Cerulli Anticipates $84 Trillion in Wealth Transfers Through 2045, (Jan. 20, 2022), https://www.cerulli.com/press-releases/cerulli-anticipates-84-trillion-in-wealth-transfers-through-2045.
[4] G.L. ch. 190B, § 2-102; G.L. ch. 190B, § 2-114; G.L. ch. 190B, § 2-705.
[5] G.L. ch. 190B, § 2-301; G.L. ch. 190B, § 2-302.
[6] G.L. ch. 190B, § 2-804.
[7] See Matter of Estate of Stacy, 96 Mass. App. Ct. 447 (2019).
[8] See 2026 Alzheimer’s Disease Facts and Figures, Alzheimer’s Association, https://doi.org/10.1002/alz.71345.
[9] See Matter of Estate of Urban, 102 Mass. App. Ct. 284, 292 (2023).
[10] See Howe v. Palmer, 80 Mass. App. Ct. 736 (2011).
[11] See Bridget J. Crawford et. al, Wills Formalities in a Post-Pandemic World: A Research Agenda, Vol. 2021, University of Chicago Legal Forum, 93, 111-12 (2021), https://chicagounbound.uchicago.edu/cgi/viewcontent.cgi?article=1685&context=uclf.
[12] See Lindsay Rawson, Lockdown Wills: Is Your DIY Will Valid?, Howells Solicitors (Jan. 21, 2026), https://howells.law/newsroom/lockdown-wills-is-your-diy-will-valid/; see also Mobley Brown LLP, The Hazards of DIY-ing Your Estate Planning During COVID-19 (Sep. 16, 2020), https://mobleybrownlaw.com/the-hazards-of-diy-ing-your-estate-planning-during-covid-19/ (explaining online fill-in-the-blank wills often considered invalid often defective); see also Matter of Estate of Olson, 103 Mass. App. Ct. 842, 849-50 (2024), review denied, 494 Mass. 1102 (2024) (holding “holographic,” or DIY, wills not valid under Massachusetts statutory law because legislature deliberately omitted exception).
[13] See Byran Borzykowski, Americans Rush to Make Online Wills in the Face of the Coronavirus Pandemic, CNBC (Mar. 25, 2020), https://www.cnbc.com/2020/03/25/coronavirus-pandemic-triggers-rush-by-americans-to-make-online-wills.html?msockid=30fd33c7c11d66ef3c2824a6c011672e (explaining informal COVID wills have increased probate litigation).
[14] See Board of Governors of the Federal Reserve, Compare Wealth Components Across Groups (last updated June 18, 2026), https://www.federalreserve.gov/releases/z1/dataviz/dfa/compare/chart/#quarter:138;series:Assets;demographic:generation;population:all;units:levels.
[15] See SJKP Law Firm LLP, Property Conveyance: How Valid Deeds Transfer Real Estate Title (June 19, 2026), https://www.daeryunlaw.com/us/practices/detail/property-conveyance (explaining complexities of conveying real property, in general).
[16] See § 31:43. Devise of real estate to two or more persons, 5B Mass. Prac., Methods Of Practice Methods of Practice § 31:43 (4th ed.) (explaining complexities of language required to convey real property to multiple heirs)
[17] See Old Colony Trust Co. v. Wolfman, 311 Mass. 614, 615-616 (1942).
Daniel Walsh-Rogalski is a litigation attorney with an emphasis on probate litigation at the Boston-based law firm of Conn Kavanaugh.
He can be reached at dwalsh-rogalski@connkavanaugh.com
Summer associate and law student Will Taber assisted with this article.
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