Common Mistakes to Avoid When Drafting a Will
          Drafting a will is an emotional and important step. You want your final directions to be clear, fair, and legally solid—but a small error could lead to confusion, disputes, or worse.
At Watterworth Law Offices, LLC, we understand how difficult it is to think about one’s mortality and how to protect loved ones. We’re here to help you avoid those pitfalls through careful estate planning.
Our Simsbury, CT estate planning lawyer will walk you through common mistakes to avoid when drafting a will so your documents are as strong as they can be. Contact us to schedule a consultation and start protecting your legacy.
One of the biggest mistakes is not satisfying formal requirements under Connecticut law. A will must be in writing and signed by the testator in the presence of two disinterested witnesses, who must also sign. If any of those steps are missed or done incorrectly, a probate court may refuse to admit the will.
Connecticut also doesn’t allow holographic (handwritten) or oral wills in most cases. Don’t assume informal methods will work. Instead, use estate planning procedures that align with state rules.
Using unclear or poorly defined terms is another frequent error. That might leave room for multiple interpretations and lead to disputes. Connecticut courts may declare parts of the will void if the language is too uncertain. You want to state clearly who gets what, under what conditions, and what happens if someone named predeceases you.
If a beneficiary you name in your will dies before you or is unable to take, and you don’t name alternates or give instructions, that portion of your estate could wind up under default state rules. You should name backup beneficiaries or include wording such as “if [beneficiary] does not survive me, then to [alternate beneficiary].”
Without that, parts of your plan might be left incomplete and create conflict.
Your executor (personal representative) will be the one carrying out your directions, paying debts, and distributing assets. If that person is unreliable, lacks time, or is unwilling, problems can arise. We often advise clients to choose someone who is organized, trustworthy, and able to handle responsibilities.
In some cases, appointing a professional fiduciary or attorney may make sense. Selecting the wrong person can complicate your estate planning and strain family relationships.
Many people think only about real property, bank accounts, or personal belongings—but today, digital assets are more important than ever. Without including login info, instructions, or digital account access, your heirs may be blocked from digital property, social media accounts, or cloud-stored files.
When preparing your will, include a schedule or separate memorandum detailing:
Account credentials: username, password, recovery email
Digital property: domain names, websites, crypto wallets, digital photos, intellectual property
Access instructions: who handles the accounts, if closure or transfer is desired
Leaving digital assets out is a serious oversight.
Life changes—births, deaths, marriages, divorces, acquisitions, or moves—can make a will outdated. If you don’t revisit your estate planning regularly, it may no longer reflect your wishes. We recommend reviewing your will every few years or after major life events.
Failing to update can lead to undesirable results, such as inadvertently leaving out someone or keeping references to assets you no longer own.
Most wills address major assets like real estate or investments, but neglecting personal items—jewelry, family heirlooms, collectibles—can lead to disagreements. One way to handle this is to include a personal property memorandum that refers to a list you can update over time without rewriting the will.
If you don’t do that, heirs may contest or fight over items you thought were insignificant—yet meaningful.
A will only takes effect upon death, but what about if you become incapacitated? If you don’t include documents such as a durable power of attorney or an advance health care directive, your loved ones may face legal hurdles to make decisions for you.
Even though such documents are often separate from the will, effective estate planning should integrate them so you’re cared for during life, not just after death.
Many assets pass outside the will—life insurance, retirement accounts, payable-on-death bank accounts, or jointly held property. If beneficiary designations conflict with your will, the nonprobate designations control.
You need to check beneficiary forms, titling of property, and whether joint ownership or TOD/POD designations match your estate planning intentions. Failure to coordinate leads to outcomes you didn’t intend.
A residuary clause handles leftover assets not specifically addressed. Without it, assets you forget to mention could pass via intestacy rules rather than your wishes.
You should include a residuary clause like “all the rest, residue, and remainder of my estate” and name beneficiaries (and alternates) for that residue. That helps your estate planning be complete and avoid gaps.
If you’ve made older wills, but don’t clearly revoke them in your new will, a court could interpret both or think they’re ambiguous. A simple clause saying “I hereby revoke all prior wills and codicils” at the start is vital. That avoids confusion and keeps your current wishes in control of your estate planning.
Many think DIY or online templates are enough. But those tools often lack customization, state-specific terms, or error-checking. In Connecticut, failing to meet formalities, including ambiguous language or missing state provisions, can invalidate the will. While templates may reduce cost, they risk undermining your entire estate planning strategy.
Even though Connecticut currently doesn’t impose a state-level estate tax for many estates, federal estate or gift tax rules may apply. Creditors or claims against your estate can also erode what remains for your beneficiaries.
A well-drafted will should allow your executor to address debts before distribution, and may include provisions to minimize liability. Failing to plan for tax or creditor matters can reduce the value passed on to heirs.
If you own property outside Connecticut, like in another state, that property may require ancillary probate there. Your will should account for multi-state assets and perhaps direct how cross-jurisdiction holdings are handled. Without that, your estate planning may be fragmented across states, adding delay and cost.
Because wills have serious consequences and small mistakes can invalidate parts, it’s wise to have a review by someone skilled in estate planning. An experienced estate planning lawyer can spot gaps, correct ambiguous language, and check formal compliance. We encourage you not to skip that review—your will is too important for unchecked assumptions.
We’re here to help clients across Simsbury, Hartford County, Litchfield County, and Tolland County with careful, thoughtful drafting from our Simsbury, Connecticut office.
Having walked through common mistakes, you can see how many things can go wrong in will drafting. Solid estate planning can prevent confusion, costs, and conflict. Contact Watterworth Law Offices, LLC today, and let us support your estate planning with clarity and care.