Cunningham's Counsel Corner

Beyond foolish misuse of AI-hallucinated fake case law, AI has now forced Courts to confront a fundamental question underlying the attorney-client privilege and work-product doctrine: when legal analysis, communications, or factual narratives are generated using AI systems, does privilege attach or is confidentiality lost.

The recent Southern District of New York decision in US v. Heppner, 1;25-cr-00503-JSR (S.D.N.Y. Feb. 2026), directly addresses this issue. Judge Rakoff held that documents created by a criminal defendant, using Claude AI, and later shared with counsel ...

Data Loss Prevention (DLP) policies in law firms are fundamentally about protecting client confidences and preserving privilege, not merely about cybersecurity hygiene or stopping rogue lawyers/groups from stealing away like thieves in the night.

DLPs capture a laundry list of Rules of Professional Conduct: 1.1 (Competence), 1.4 (Communications),1.6 (Confidentiality), 1.9 (Former Clients), 1.15 (Safekeeping Property), 3.4 (Fairness to Opposing Party and Counsel), 4.4 (Respect for Rights of Third Persons), 5.1 (Supervisors), 5.2 (Supervised Attorneys), 5.3 ...

Your law firm partnership agreement (operating agreement, etc.) rewrite for an established but growing law firm should be approached as your governance modernization project, not merely an economic reset.

The agreement should expressly anchor the law firm’s structure and decision-making to compliance with your jurisdictions' Rules of Professional Conduct, ensuring that growth, compensation, lateral hiring, marketing, and tech adoption are filtered through professional-responsibility obligations rather than merely business pressures.

Expressly grounding your ...

ABA Model Rule 1.5 and the Lodestar analysis occupy related but fundamentally distinct spaces in the regulation and evaluation of attorney’s fees. Both frameworks revolve around reasonableness, yet they serve different purposes, apply at different junctures of the legal representation, and reflect different priorities.

Rule 1.5 is grounded in professional responsibility and ethics, while the Lodestar method is a judicially created economic tool used primarily in fee-shifting contexts outside of the traditional "American Rule" where litigants pay their own attorneys ...

Tabletop simulations transform legal ethics training from a passive (and boring) CLE into a live-fire exercise. Pressure-test how your lawyers and staff respond to real-time ethical dilemmas to revealing how stress, ambiguity, and urgency can erode judgment. Simulations allow law firms to observe how well your lawyers understand and apply the Rules of Professional Conduct under real world conditions, and how your internal communications, escalation systems, and response planning perform in crisis conditions.

Disaster doesn't ring your door bell announcing "this is a Rule ...

Lawyers are trained and praised for our zeal. Model Rule 1.3 (Diligence) requires that a lawyer “act with reasonable diligence and promptness in representing a client,” with Comment [1] requiring "zeal in advocacy upon the client's behalf." Yet that duty does not justify unrestrained combativeness, misrepresentation, or disregard for the rights of others. The Preamble to the Model Rules explicitly warns that a lawyer must also be “a public citizen having special responsibility for the quality of justice.” When zeal crosses into misconduct, the consequences can be swift ...

Better for you, your law firm, AND your clients.

Arbitration agreements in client engagement letters are a key element of law firm risk management. By addressing dispute resolution at the outset of the attorney–client relationship, law firms can reduce exposure to drawn-out public litigation, manage costs, and bring greater predictability to malpractice and fee disputes.

Benefits for Law Firm Risk Management

Arbitration provisions in engagement agreements can provide law firms with a valuable safeguard against the unpredictability of traditional litigation. One of the ...

Staten Island resident, Richard Hoffmann, is making headlines for choosing to represent himself as a defendant in a civil lawsuit against his former employer using AI tools such as ChatGPT, Gemini, and Grok. Hoffmann called his strategy a “checkmate,” boasting that the AI helped him draft pleadings, simulate arguments, and file motions without the expense of retaining an attorney. That's Fenix Capital Funding LLC v. Hoffmann, Richmond County Supreme Court, Index No. 151973/2025, for anyone that wants to follow along.

“I used AI to game out every possible move,” said ...

Clarity is our most powerful tool, with ambiguity being pure liability. Attorney-client engagement agreements are contracts, viewed by Courts and Attorney Disciplinary Committees with the (appropriate) skepticism of a contract of adhesion. One of the most effective ways law firms can protect themselves is by precisely defining and documenting the scope of representation.

This risk management best practice is grounded in ABA Model Rule 1.2(a), which states: “A lawyer shall abide by a client’s decisions concerning the objectives of representation and… shall consult ...

I got a bad result for a client last week. It was totally expected but still hurts. I'd explained the risks, prepared him for the outcome, (documented everything) and mentally braced myself. But when the decision came in, there was still that sinking feeling. Not just for the client but for me too. It's not that I believed we would win, but that familiar ache crept in, the one that comes with not being able to change the ending.

This is a warning bell for compassion fatigue begins. It starts small and slow, not with the dramatic collapse of mental health, but an unnoticed erosion of emotional ...