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Compliance

+3

The Play — Issue #23: Fifty-Four Percent, and That Was the Good Number

Sep 28, 2026

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10 min read

The Play — Issue #23: Fifty-Four Percent, and That Was the Good Number

A private answer key for grading legal AI, four vendor defaults that flip in thirty days, a token price cut that may not lower the bill, and what OpenAI's own agents did last week.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #22: Slowing Down AI?

Sep 15, 2026

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7 min read

The Play — Issue #22: Slowing Down AI?

An evaluator who does not report to the buyer, Latham's own GPU servers, Morgan & Morgan's four percent, and the gap between using AI and deploying it.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #21: The Fix Never Reached the Template

Sep 11, 2026

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6 min read

The Play — Issue #21: The Fix Never Reached the Template

Four plays: fake citations that lived in a go-by, a filing whose metadata named its author, a D.C. judge's cite-check model against California's, and ChatGPT's forward-only off switch.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #20: The Safe Harbor Your Email Server Closed

Aug 31, 2026

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7 min read

The Play — Issue #20: The Safe Harbor Your Email Server Closed

Four plays: Rule 11 service you can prove, the reprimand that never expires, California's last day, and the fake law arriving from the other side.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #19: Your Legal AI Vendor Is Now a Connector

Aug 26, 2026

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7 min read

The Play — Issue #19: Your Legal AI Vendor Is Now a Connector

Four Points: renegotiate before you sign, read what California actually amended, fix the taxonomy the connector inherits, and watch who is building the plumbing.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #18: Every Citation Was Real

Aug 24, 2026

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6 min read

The Play — Issue #18: Every Citation Was Real

Four plays: a position check your cite-check cannot run, the appendix that ended a case, twenty-five dollars a client, and a sanction the lawyer cannot bill.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #17: The Notetaker Kept a Copy for Itself

Aug 17, 2026

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8 min read

The Play — Issue #17: The Notetaker Kept a Copy for Itself

A federal court drew the line between a tool and a party, and Otter landed on the wrong side. Plus the legal AI tool nobody vetted, and a mark inside your drafts.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #16: Your Vendor Has Vendors

Aug 12, 2026

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6 min read

The Play — Issue #16: Your Vendor Has Vendors

The LexisNexis outage happened on somebody else's servers. Plus the NYC Bar on recording anyone who isn't your client, and the model providers moving into implementation.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Aug 10, 2026

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5 min read

The Play — Issue #15: The Agent Didn't Access Anything. You Did.

Matthew Roberts
Matthew Roberts

legal-ops

+3

The Play — Issue #14: Nobody at Your Firm Bought the Bot in the Room

Aug 5, 2026

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6 min read

The Play — Issue #14: Nobody at Your Firm Bought the Bot in the Room

A researcher found 180,000 call records sitting open in January. The vendor never answered, and it was still open yesterday.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #13: The Word Document That Edits Your Work On the Way Out

Aug 3, 2026

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5 min read

The Play — Issue #13: The Word Document That Edits Your Work On the Way Out

One play: decide which inbound documents your AI assistant is allowed to read. Plus a firm insuring its agents, Goldman's stake in Harvey, and the $1,500-per-citation math.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #12: The Layer Beneath Your AI Tools

Jul 31, 2026

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5 min read

The Play — Issue #12: The Layer Beneath Your AI Tools

Three plays: the real AI vendor lock-in, validating an agent-led contract migration, and a ruling that could decide whether AI training needs a license.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #11: The Next Bad Citation in Your Case Won't Be Yours

Jul 29, 2026

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6 min read

The Play — Issue #11: The Next Bad Citation in Your Case Won't Be Yours

Three plays: check the other side's citations, put a source cite on every fact, and cut your biggest AI project down to one input and one output.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #10: Your AI Policy Governs the Keyboard

Jul 27, 2026

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8 min read

The Play — Issue #10: Your AI Policy Governs the Keyboard

Four plays: inventory what your AI tools can reach, move your policy from approved-tool to verified-citation, audit your engagement letter, and score build-vs-buy on maintenance.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #9: The AI Failure That Doesn't Leave a Trace

Jul 22, 2026

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5 min read

The Play — Issue #9: The AI Failure That Doesn't Leave a Trace

Three plays: spot-check for the AI failures that show no error signal, clean your document corpus before you connect AI to it, and bring a real number to the pricing conversation.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #8: Your AI Prompts May Be Discoverable. Here's How to Protect Them.

Jul 20, 2026

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5 min read

The Play — Issue #8: Your AI Prompts May Be Discoverable. Here's How to Protect Them.

How to structure AI-assisted document review so your prompts survive a motion to compel, plus the single-agent consolidation pitch and reading your vendor's roadmap.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #7: Your Malpractice Carrier Is Already Asking This Question

Jul 17, 2026

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5 min read

The Play — Issue #7: Your Malpractice Carrier Is Already Asking This Question

Spellbook's autonomous contract AI, a malpractice insurance gap nobody's checked, and Reed Smith's consolidated AI unit

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #6: The Warning Said Months. It Took Nine Days.

Jul 13, 2026

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4 min read

The Play — Issue #6: The Warning Said Months. It Took Nine Days.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #5: A Legal AI Unicorn Just Broke the Billable Hour

Jul 10, 2026

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5 min read

The Play — Issue #5: A Legal AI Unicorn Just Broke the Billable Hour

Norm Ai's outcome-based unicorn, a data-license fight that predates gen AI, and BigLaw's $440K hiring problem

Compliance

+3

The Play — Issue #4: Both Sides Just Tore Up the AI Contract

Jul 8, 2026

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4 min read

The Play — Issue #4: Both Sides Just Tore Up the AI Contract

Buyers are cutting terms to a year. Vendors are un-fixing prices. Your next renewal is the play.

Compliance

+3

The Play — Issue #3: Five Governments Say AI Cyberattacks Are Months Away

Jul 6, 2026

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4 min read

The Play — Issue #3: Five Governments Say AI Cyberattacks Are Months Away

A joint intelligence warning, a Kirkland exclusivity deal, and the court rules catching up to Issue #1.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #2: Washington Pulled the Plug on a Frontier AI Model

Jul 3, 2026

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4 min read

The Play — Issue #2: Washington Pulled the Plug on a Frontier AI Model

If your AI tools depend on a frontier model API — and they probably do — this is what a government-ordered shutdown actually looks like.

Matthew Roberts
Matthew Roberts

Compliance

+3

The Play — Issue #1: The Ninth Circuit Just Ended the 'I Didn't Know' Defense

Jul 1, 2026

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5 min read

The Play — Issue #1: The Ninth Circuit Just Ended the 'I Didn't Know' Defense

A precedential ruling and a new Florida rule mean sanctions are coming for legal-grade AI tools too — not just ChatGPT.

The Play Newsletter

Practical AI for law firm operators. Not theory, not vendor pitches. What's going on and what's actually working, from someone running it.

© 2026 The Play Newsletter.
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