Virginia Executors: 10 Warning Signs a Beneficiary May Contest the Will
Date: March 12, 2026
Being named as executor of an estate in Virginia is a significant responsibility. You are expected to administer the estate according to the terms of the will, manage assets prudently, and act in good faith toward all beneficiaries. But what happens when a beneficiary, or someone who expected to be a beneficiary, decides to challenge the will you are tasked with carrying out?
Will contests are among the most common and emotionally charged types of estate disputes in Virginia. For executors, they can also be the most disruptive, potentially delaying the administration of the estate and creating personal liability concerns. Recognizing the warning signs early allows you to take proactive steps, including consulting with an experienced estate litigation attorney, before a challenge is formally filed.
Below are ten warning signs that a beneficiary or other interested party may be preparing to contest the will. And if you believe you need legal advice for a complex will, trust or estate problem then you can contact our attorney team for a confidential consultation.
1. The testator made major changes to the will or estate plan shortly before passing.
An executor may already be aware that the will you are probating reflects recent changes. If those changes were made in the months or weeks before the testator’s death, particularly while the testator was ill or suffering from diminished faculties, expect that disinherited or reduced beneficiaries may raise concerns about undue influence or lack of testamentary capacity.
2. Family members are asking pointed questions about how and when the will was executed.
When beneficiaries or family members begin asking detailed questions about the circumstances surrounding the execution of the will, who was present, which attorney drafted it, whether the testator was alert and aware, this can signal that they are evaluating the grounds for a challenge. A lack of transparency in your responses, whether intentional or not, can escalate their concerns and increase the likelihood of a formal contest.
3. The testator was visibly declining in physical or mental health around the time the will was executed.
If family members witnessed the testator’s declining health — confusion, memory loss, difficulty communicating — around the same time the will was signed, they may argue the testator lacked testamentary capacity. An executor should be prepared for this line of challenge and understand that medical records and witness testimony from this period will be closely scrutinized.
4. Beneficiaries are telling conflicting stories about the testator’s stated intentions.
If family members come to you insisting the testator had always promised them a specific inheritance, or that the testator’s longstanding plan looked nothing like the current will, take this seriously. When the will substantially deviates from what the testator communicated to family over many years, specially without explanation, that gap can become the basis of a will contest.
5. The testator used an unfamiliar attorney to draft the new will.
If the testator had a longtime attorney or law firm that handled prior estate planning documents but then used a different, unfamiliar attorney to draft the most recent will, beneficiaries may view this with suspicion. The concern deepens if that new attorney has a pre-existing relationship with someone who benefits significantly under the new will. An executor may want to note that challengers may subpoena the drafting attorney’s files.
6. Non-family members or new acquaintances are named as beneficiaries.
While a person is free to leave their property to whomever they choose, the inclusion of caretakers, neighbors, or new acquaintances as major beneficiaries, particularly at the expense of close family, is a common trigger for a will contest. For an executor, if the will being administered reflects this pattern, they should anticipate that family members may allege undue influence.
7. Communications between family members and beneficiaries have turned hostile.
After the testator’s passing, if an executor begins receiving hostile emails, letters, or phone calls from family members or their attorneys, this is often a precursor to a formal will contest. Accusations of wrongdoing, demands for documents, or threats of legal action should not be ignored.
8. Personal property is missing from the estate or was allegedly “gifted” before death.
Executors are responsible for marshaling the testator’s assets. If property that family members expected to find is missing, or if someone claims the testator gave valuable items to them as gifts near the end of life while the testator was ill or suffering from diminished faculties, this can trigger both a will contest and separate claims for recovery of those assets.
9. Beneficiary designations on financial accounts or insurance policies were recently changed.
If you are an executor, you may discover during the administration of the estate that beneficiary designations on the testator’s bank accounts, investment accounts, or life insurance policies were changed shortly before death. If those changes benefited someone new while the testator was ill or suffering from diminished faculties, this can be a red flag that a broader estate dispute or will contest is developing.
10. Long-estranged family members have re-appeared and are now beneficiaries.
If a family member who had little or no contact with the testator for years suddenly re-appeared shortly before the testator’s passing and is now a significant beneficiary under the will, other family members may see this as evidence of undue influence or manipulation. As executor, be prepared for questions about the nature and timing of that reconnection.
Each ground for a will contest has different elements, and as executor, you may find yourself in the difficult position of defending the will while navigating family conflict. If you are an executor in Virginia dealing with any of the above warning signs, you should promptly consult with an experienced estate litigation attorney to understand your obligations, your potential exposure, and your options.
About Our Estate Litigation Team
Each ground for a will contest has different elements, and as executor, you may find yourself in the difficult position of defending the will while navigating family conflict. If you are an executor in Virginia dealing with any of the above warning signs, you should promptly consult with an experienced estate litigation attorney to understand your obligations, your potential exposure, and your options.
About Our Estate Litigation Team
Whiteford offers sophisticated, experienced counsel on estate, trust, and fiduciary dispute matters, including will contests.
When a will contest is on the horizon, the stakes are personal and the legal questions are complex. Whiteford’s Estates, Trusts, & Fiduciary Litigation Practice Team in Richmond, Virginia helps executors, trustees, heirs, and beneficiaries navigate these disputes — from early warning signs through trial. Our attorneys handle claims involving undue influence, fraud, lack of testamentary capacity, breach of fiduciary duty, and contested transfers of assets, as well as guardianship and conservatorship proceedings and will and trust interpretation.
Brett C. Herbert is a partner at Whiteford, Taylor & Preston LLP in Richmond, Virginia. Brett is a litigator and member of the Estates, Trusts, & Fiduciary Litigation Practice Team who represents clients in will contests, trust challenges, and breach of fiduciary duty claims involving executors and trustees, among other similar claims. He also handles guardianship and conservatorship proceedings, including both routine and contested matters. Brett has been recognized as a Virginia Super Lawyers "Rising Star" and named to Best Lawyers in America® Ones to Watch in Trusts and Estates. Brett can be reached at BHerbert@whitefordlaw.com and (804) 977-1242.
Gregory S. Bean is a partner at Whiteford, Taylor & Preston LLP in Richmond, Virginia. Greg is a litigator and member of the Estates, Trusts, & Fiduciary Litigation Practice Team who represents clients in will contests, trust challenges, and breach of fiduciary duty claims involving executors and trustees, among other similar claims. His practice extends to will and trust interpretation, guardianship and conservatorship matters, and power of attorney disputes. Greg holds a Best Lawyers in America® distinction in Trusts and Estates. Greg can be reached at GBean@whitefordlaw.com and (804) 977-1241.
The information contained here is not intended to provide legal advice or opinion and should not be acted upon without consulting an attorney. Counsel should not be selected based on advertising materials, and we recommend that you conduct further investigation when seeking legal representation.