The Common Challenges Faced During the Probate Process

The single most expensive probate challenge in New York is a contested will. An adversely affected distributee or prior-will beneficiary has a statutory right under SCPA § 1404 to examine the attesting witnesses, the supervising attorney, and (where applicable) the drafter before deciding whether to file objections. The examinations are sworn depositions, take two to four months to schedule and complete, and produce the evidentiary record on which both sides assess the strength of the contest.

If formal objections follow under SCPA § 1410, the proceeding enters litigation: document discovery, fact-witness depositions, expert reports on capacity and handwriting, summary judgment motions under CPLR § 3212, and ultimately a bench trial before the Surrogate. The full sequence routinely consumes eighteen months to three years. Preliminary Letters Testamentary under SCPA § 1412 should be obtained early so the proposed executor can pay taxes and preserve assets during the contest.

Most contests settle. A negotiated settlement agreement under SCPA § 2107 — typically a reallocation of the residue, a lump-sum payment to the objectant, or appointment of a neutral co-executor — preserves estate value that would otherwise be transferred to counsel. We evaluate contest risk at the petition stage, build the record to defeat objections, and negotiate hard when the economics favor settlement.

Every New York probate executor must publish notice to creditors under SCPA § 1801 in a newspaper of general circulation in the decedent's county. Publication starts the seven-month claim period — the single longest fixed delay in any probate. Creditors who present timely written claims must be evaluated by the executor and either paid or formally rejected. A rejection limits the creditor's time to commence suit under EPTL § 11-1.5.

Medicaid liens are the most consequential single category of creditor claims. Under federal law and Social Services Law § 369, the New York State Department of Health may recover from the estate of a Medicaid recipient who died age 55 or older, up to the amount of benefits paid. Liens are routinely filed against estates that include any real estate or significant cash. The lien must be reviewed, negotiated where possible, and resolved before distribution; payments in error become surcharge exposure for the executor.

Other recurring creditor categories include credit card debt, medical bills (frequently incurred in the decedent's final months), residual federal and state income tax, mortgage balances, and HOA arrears. The executor must distinguish between debts of the decedent (paid from estate assets in EPTL § 1902 priority order) and debts of the executor's administration (administration expenses, paid first). Misclassification creates personal liability.

New York imposes its own estate tax independent of the federal estate tax. The New York exemption is approximately $7.35 million, while the federal basic exclusion amount for 2026 is $15,000,000 per person and permanent under Public Law 119-21. The gap between the two is where most New York estate-tax planning happens, and where most under-prepared estates pay tax they could have avoided with a properly drafted credit-shelter or QTIP plan.

The New York cliff is uniquely punitive. Estates with a taxable value greater than 105% of the exemption (roughly $7.72 million) lose the exemption entirely — the full estate is taxed from dollar one. An estate just over the cliff pays meaningfully more New York estate tax than one just under it. The cliff is the central drafting problem for high-net-worth New Yorkers and requires lifetime gifting, charitable transfers, or careful credit-shelter funding to avoid.

Federal Form 706 and New York ET-706 are due nine months after the date of death. Extensions of time to file (not to pay) are routinely granted on Form 4768. The fiduciary income tax (1041 and IT-205) covers income earned by the estate during administration. Late filings carry interest and penalties that fall on the executor personally if estate funds were available; estate-tax mistakes are a leading source of fiduciary surcharge claims.

The inventory required under Uniform Rule 207.20 must report every probate asset at its date-of-death value. Bank and brokerage accounts are simple — the statement establishes the figure. Publicly traded securities are valued at the mean of the high and low trade prices on the date of death. Tangible personal property of significant value (jewelry, art, collectibles) requires a qualified appraisal.

Real estate is the most frequent valuation flashpoint. The executor obtains a qualified appraisal — not a Zillow estimate, not the property's last assessed value — and uses it for both the inventory and the estate tax return. Sale below the appraised value triggers questions; sale above it can trigger income tax recognition. Disputes among beneficiaries about whether to sell, rent, or distribute the real property in kind frequently slow the proceeding by months.

Closely held business interests are the most complex. A qualified business valuation, prepared by a credentialed appraiser, accounts for control premiums, marketability discounts, key-person reliance, and the specific facts of the business. The valuation drives estate tax, beneficiary distribution, and (if a buy-sell agreement exists) the price at which co-owners may redeem the interest. We coordinate with credentialed valuation firms on every estate that includes a privately held business.

Family conflict accelerates almost every other probate problem. Co-executors who cannot agree slow every decision. Beneficiaries who suspect favoritism demand judicial accountings rather than settling for informal releases. Step-parent and second-marriage situations produce surviving-spouse elections under EPTL § 5-1.1-A. Estranged adult children resurface to object. Each of these dynamics is normal; each must be managed.

Communication discipline is the single most effective fiduciary practice. Quarterly written updates to all interested parties, copies of significant filings, advance disclosure of proposed distributions, and prompt answers to beneficiary questions reduce contests far more than they cost. The executor is not required to act through counsel for every communication, but routing significant decisions through counsel creates a record and forecloses later 'I never agreed to that' disputes.

Where the conflict is irreconcilable — co-executors deadlocked, an executor accused of self-dealing — SCPA § 711 authorizes the court to revoke Letters and remove the fiduciary. The standard is high (misconduct, dishonesty, want of understanding, or other conduct demonstrating unfitness), but removal is granted in clear cases. A neutral administrator c.t.a. can finish the administration without the personal entanglements that disabled the original fiduciary.