Two Wills, Different Handwriting, One Father Gone

The situation

For most of Pensri's adult life, her father's estate plan had been unremarkable and settled. He was a partner in an Ottawa engineering firm he had built from a two-person partnership into a firm with a regional reputation, and Pensri had followed him into the practice, making partner herself six years earlier. His will, drafted a decade before his death, left the bulk of his estate, roughly $4.2 million once his firm interest, investment portfolio and two properties were valued, to Pensri, with a smaller specific gift set aside for his second wife, Azadeh, an anesthesiologist he had married eight years before his death. Pensri was named executor. It was the kind of plan families rarely think about twice, because nothing about it seemed to be in question.

Her father died after a short illness, and the plan that had sat quietly for ten years suddenly did not hold. Within weeks of the funeral, Azadeh's lawyer produced a different will, dated less than two months before his death, that reversed the earlier arrangement almost entirely. Under this second document, Azadeh received the bulk of the estate, with a significant portion also directed to her adult daughter Shirin, and Pensri's share reduced to a modest fixed sum.

Both wills, on their face, looked properly executed. Both carried signatures, dates, and witness attestations that appeared regular. Pensri had no immediate way to know, just by looking at the two documents side by side, which one actually reflected her father's wishes at the time he died.

What made the situation harder than the paperwork alone was money, ironically, given the size of the estate on paper. Almost everything her father owned was tied up in his firm interest and two properties, none of it liquid, and none of it accessible to Pensri while the two wills were in dispute. She was, on paper, the likely heir to millions, and in practice she had to fund a legal fight over that inheritance largely out of her own more modest personal savings.

Pensri had spent her whole career working alongside her father at the firm they now both had a stake in, and the ordinary plan, the one that had sat untouched for a decade, had never felt like something that needed defending. She had assumed, the way most adult children do, that the will she vaguely knew existed would simply do what her father had always said it would. Discovering a second will she had never heard of, produced by her stepmother's lawyer within weeks of the funeral, was disorienting in a way that had nothing to do with money at first and everything to do with how quickly a settled picture of her father's intentions had come apart.

Her relationship with Azadeh had never been openly hostile, though it had also never been especially close. The two had maintained a polite distance for eight years, the kind of relationship that works well enough at family dinners and falls apart entirely once real money is on the table.

What the law actually said

When two apparently valid wills exist, Ontario law generally treats the most recent one as governing, provided it was validly made, which meant the second will's later date gave it the presumptive advantage rather than Pensri's. That reality needed to be faced directly rather than avoided: the fight was not about which will was older and therefore preferred, it was about whether the second will could withstand scrutiny on how it came to be signed.

A will can be set aside, or its validity seriously challenged, on a narrow set of grounds: that the person did not have the mental capacity to understand what they were signing, that they were subject to undue influence from someone positioned to benefit, or that the document was not executed with the formalities Ontario law requires, such as being properly signed and witnessed. Simply being surprised, or believing a result is unfair, is not on its own a ground to challenge a will.

Here, the timing was the first thing worth examining closely. The second will was signed less than two months before death, during a period when Pensri's father was already unwell and increasingly dependent on Azadeh for daily care, a circumstance that does not by itself prove undue influence but does raise the kind of questions courts take seriously, particularly when the person who arranged for the new will to be made is also its primary beneficiary.

The second consideration was capacity. A late-life will made during declining health is not automatically suspect, since people are entitled to change their estate plans for good reasons right up until they lack the capacity to do so. What mattered was evidence: medical records from that period, and the file of the lawyer who prepared the second will, would show whether anyone had turned their mind to capacity and independence at the time, or whether the will had simply been signed with no such safeguards in place.

There was also a formalities question worth checking, though it turned out to be a dead end. Ontario's execution requirements for a will are specific but not complicated, and the second will's signature and witnessing appeared to meet them on their face. Ruling that avenue out early, rather than spending time and money probing something that was unlikely to go anywhere, was itself part of keeping the investigation focused on the questions most likely to actually matter.

What we did

1. Set a fixed investigative budget with Pensri from the outset, given her limited liquid funds relative to an estate she could not yet touch, and agreed the case would not proceed to a full contested hearing unless the early evidence justified that expense. That agreement kept every subsequent step deliberately targeted rather than open-ended, and gave Pensri a hard number she could actually plan around instead of an open-ended legal bill.
2. Requested the deceased's medical records from the two months before the second will was signed, and separately the file of the lawyer who prepared it. The medical request focused narrowly on that window, rather than his full history, to establish what his treating physicians had observed about his cognitive state at the relevant time. The lawyer's file mattered because a properly prepared will of this kind should show independent contact with the client and some inquiry into capacity, not just a signature at the end.
3. Identified that Azadeh had arranged the appointment and driven her husband to it without Pensri or any other family member's knowledge, a detail that, combined with the short time frame and his declining health, meaningfully strengthened the case that the circumstances warranted closer scrutiny rather than being dismissed as an ordinary late-life update to an estate plan.
4. Interviewed a small number of people close to the family, including a longtime colleague at the engineering firm who had spoken with Pensri's father in his final weeks, to build a picture of his stated intentions outside of the disputed document itself, done briefly and without turning the process into a broad-based investigation the budget could not support.
5. Found that the second will's file contained no independent capacity assessment, then compiled the findings into a concise position summary. The missing assessment was, on its own, not conclusive, but it was significant given how much had changed in the will and how briefly before death it was signed, so we set out the medical and drafting evidence plainly and sent it to Azadeh's lawyer with an invitation to resolve the matter.
6. Negotiated a settlement directly from that position, then finalized terms that substantially upheld the original will. A full trial carried real risk and cost for both sides, and the evidence gathered gave Pensri enough leverage to negotiate without spending the case's remaining budget testing it in court, landing on a modest increase to Azadeh's specific gift beyond what the first will provided in exchange for both sides agreeing not to pursue the matter further.
7. Confirmed the settlement in a signed release binding on all parties, including Shirin, so no aspect of the dispute could resurface later once the estate began transferring assets under the agreed terms, and coordinated the timing of the firm interest transfer with the firm's own partnership requirements to avoid unnecessary friction with Pensri's fellow partners, who had watched the dispute play out from inside the same office.

The outcome

The estate was ultimately distributed on the terms of the original will, with the bulk of the roughly $4.2 million estate passing to Pensri as her father had arranged a decade earlier, and Azadeh receiving a specific gift somewhat larger than the original will had provided, agreed as part of the settlement rather than imposed by a judge. Shirin, who stood to inherit under the second will, received nothing under the final arrangement, and confirmed in writing that she would not pursue any further claim against the estate.

The case never reached a contested hearing. The investigative work, kept deliberately narrow because of what Pensri could actually afford to spend, produced enough evidence about the circumstances of the second will's signing that Azadeh's side had good reason to settle rather than test it in court, where the outcome and the cost were both less certain.

Azadeh, for her part, faced her own version of the cost pressure that shaped the settlement. Contesting the outcome further would have meant defending, at a hearing, exactly how and when the second will had come to be signed, a prospect that carried its own risk for her regardless of how the evidence was ultimately assessed.

Pensri's own legal spending stayed within the budget set at the outset, a result that mattered as much to her as the distribution itself, since she had spent months worried about outspending an inheritance she might never see. The firm interest and properties, illiquid throughout the dispute, were transferred and, where necessary, sold in an orderly way once the settlement resolved which will governed the estate.

Looking back, Pensri has said the hardest part was not the legal uncertainty but the months of not knowing, while managing her own household budget carefully, whether the fight would end with the plan her father had described to her for years or with almost nothing. The discipline of setting a budget for the investigation at the very start, and sticking to it even when emotions ran high, was what made it possible to reach a resolution she could actually afford to pursue.

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