Most estate planning pitfalls are not the result of how the estate plan was drafted. They are the result of small oversights such as a form that was never updated, a trust that was never funded, or a beneficiary designation that still reflects a prior marriage. These mistakes are predictable, which means they are also preventable.
The Unfunded Revocable Trust
The single most common Massachusetts estate planning mistake is signing a revocable trust and never funding it. A trust is a set of instructions for managing and distributing property, but if the property was never retitled or directed into the trust, those instructions have nothing to manage.
Funding means changing the title on assets so the trust (not the individual) is the owner, or changing the beneficiary on accounts so they pass to the trust at death.
A pour-over will catches unfunded assets and sends them to the trust after death, but those assets still pass through probate first. The reason most clients establish a revocable trust is to reduce probate exposure, but an unfunded trust defeats the purpose.
Stale Beneficiary Designations
Retirement accounts, life insurance, annuities, and payable-on-death accounts transfer directly to named beneficiaries at death, regardless of what the will says. This is one of the most powerful tools in estate planning and also one of the most common sources of error.
Common patterns of stale designations include:
Under MGL c. 190B, section 2-804, Massachusetts law revokes the designation of a former spouse on certain nonprobate transfers after a divorce. But this statute does not override federal ERISA preemption. The United States Supreme Court held that for ERISA-governed retirement plans (most employer-sponsored 401(k)s and pension plans), the beneficiary form on file controls regardless of state law revocation-on-divorce statutes. A participant who was divorced in 2010 and who never updated the 401(k) beneficiary form has probably left the account to the former spouse even if state law says otherwise.
The only reliable fix is to review and update beneficiary designations directly, at every institution, after any major life event and at least every three to five years.
No Successor Fiduciaries Named
A will that names only a primary Personal Representative, or a trust that names only a primary trustee, has a single point of failure. If the named person cannot serve (due to death, incapacity, unwillingness, or some other disqualification), the court may appoint a replacement based on statutory priority. That replacement may not be who the testator would have chosen.
Modern plans typically name a primary fiduciary and at least two successors. Building out three or four layers of successors costs nothing in the drafting and removes the court-appointment risk entirely.
Reviewing the fiduciary chain periodically is part of a maintained plan.
DIY Documents Without Legal Review
Massachusetts law recognizes holographic wills and self-drafted wills so long as they meet the execution formalities at MGL c. 190B, section 2-502 (signature of the testator in the presence of two witnesses who also sign). Online form services and paper forms can produce a technically valid will. That does not make them a good plan.
The recurring problems with DIY estate planning include:
DIY planning is most defensible for very basic situations: a single person with modest assets, no minor children, no real estate, and beneficiaries who all have clean relationships. For most other families, the cost of a reviewed plan is a fraction of the cost of a contested or probate-heavy administration.
Overlooking the Massachusetts $2M Exemption
The federal estate tax exemption for 2026 is $15 million per person, while the Massachusetts estate tax exemption is $2 million.
A Massachusetts resident with a $4 million estate owes no federal estate tax but may owe Massachusetts estate tax. Families who assume that the federal exemption covers them often overlook Massachusetts tax exposure entirely. The Massachusetts estate tax uses a graduated rate schedule with a top marginal rate of approximately 16 percent on the largest estates.
A common Massachusetts estate tax planning technique is bypass or credit shelter trust structures for married couples (allowing each spouse to use a separate $2 million exemption). This is not handled by a standard federal-focused plan, so tailoring an estate plan to Massachusetts law is important.
Not Addressing Incapacity
Most clients think of estate planning as death planning. In reality, the documents that sometimes matter most are the incapacity documents such as the durable power of attorney and the health care proxy. A family that needs to manage finances or make medical decisions for a parent with dementia is relying on those documents, not on the will.
A plan without current incapacity planning documents may force the family into a conservatorship or guardianship proceeding through the court to get authority over financial and medical matters. These proceedings cost money and time, and they may not deliver the result the principal would have chosen if asked in advance.
Planning Ahead
Most of these mistakes are avoidable by reviewing the plan as life changes, and ensuring the plan utilizes proper tax planning tools based on Massachusetts estate tax law.
At RackiLaw, we recommend a formal plan review every three to five years, and always after a major life event. If it has been longer than that since you last looked at your documents, or if any of these situations look familiar, a review is the practical next step.