Most executors who handle an estate without counsel do so because the estate is simple in the ways that matter: one state, one house, cooperative beneficiaries, more assets than debts, and a will nobody disputes. That describes a large share of probate files. It does not describe all of them, and the difference is usually visible in the first sixty days, well before the filing deadlines that punish a wrong guess. What follows are the conditions that reliably convert an administrative task into a contested proceeding, and the specific documents a careful reader checks to find out which situation is actually in front of them.
A will that was signed late, revised late, or signed by someone who was already ill
Check the execution date against the medical record and against the date of any prior will. A will signed three weeks before death, at a hospital or a facility, revising a longstanding distribution in favor of one child or one caregiver, is the fact pattern that produces undue influence and capacity claims. Check who drove the decedent to the signing, who chose the attorney, and whether the witnesses were disinterested. None of that makes the will invalid. It does mean the contest period, typically measured in months from the notice to interested parties, is not a formality, and an executor who defends the will alone is defending it against someone who hired a litigator.
Debts that may exceed assets
Before paying anything, total the secured debt, the medical bills, the credit card balances, and any Medicaid estate recovery claim, then compare that figure to the date-of-death value of the probate assets. If the two are close, the estate is potentially insolvent, and insolvency changes the rules entirely. State statutes set a payment priority: administration expenses and funeral costs first, then certain taxes, then the general creditors, with claims in a lower class paid nothing until the class above is satisfied in full. An executor who pays a sympathetic creditor out of order can be held personally responsible for the shortfall to the creditors who should have been paid first.
Creditor claims that arrive with a lawyer attached
Check the form of every claim against the statute. Most states require a creditor to present a claim in a specified form, within a window that runs from publication of notice or from direct written notice, and a claim that misses the window is barred. That is a real defense, and it is worth asserting. But when the claimant is a hospital system, a nursing facility, or a subrogating insurer with counsel, the disallowance you file will be litigated, and the reply deadlines are short. The economics change once the amount in dispute exceeds a few months of fees.
Real property in another state
Check the deed for every parcel, including the vacation cabin and the inherited farmland nobody has visited in years. Real property is governed by the law of the state where it sits, which usually means an ancillary probate opened in that state's court, with its own filings, its own bond question, and in many jurisdictions a requirement that a nonresident personal representative appoint a local agent or engage local counsel. Two proceedings, two sets of deadlines, two sets of creditor notices. This is the trigger that catches the most people by surprise, and it is also the easiest one to spot with an hour of work.
Beneficiaries who have stopped talking to each other
Check whether anyone has asked for an accounting, hired counsel, or demanded a copy of the inventory before you offered one. Those requests are ordinary. Their timing is the signal. An executor who is also a beneficiary, who lived in the decedent's house, or who held a power of attorney during the final years is exposed to a self-dealing claim whether or not anything improper happened, and the answer to that exposure is procedural: formal accountings, court approval of significant transactions, and receipts and releases before distribution.
Distribution before the estate is actually closed
The single most expensive executor mistake is paying beneficiaries while a claim, a tax obligation, or a contest is still live. The Internal Revenue Service administers the federal tax obligations that survive a decedent, including the final individual return and the fiduciary income tax return for the estate, and a personal representative who distributes assets before those obligations are satisfied may become personally liable for the unpaid amount. Check the claims period, the tax filings, and the closing letter or discharge before writing a single check. Counsel is cheaper than the liability.
An estate with none of these features rarely needs more than a few hours of an attorney's time, often at an hourly rate for document review rather than a percentage fee. An estate with two of them is a case, and it is worth knowing which one you have before the first deadline runs.