Your AI Conversations Might Be Sold. Here’s What You Need to Know

If you use AI Chatbots and have installed certain free browser extensions, your AI conversations might be sitting in a commercial database right now, available for purchase. I know. That’s not what you wanted to read today. But this is exactly the kind of thing you need to know about, especially if you’re a lawyer, […]

I Asked AI to Summarize a Court Opinion. It Got the Holding Wrong.

One of the things I frequently warn attorneys against is trusting AI to summarize things properly. Sometimes, when summarizing the law, AI gets it completely wrong. One example is the recent Pennsylvania Superior Court opinion for Saber v. Navy Federal Credit Union. A colleague of mine sent the opinion to me, so I asked Claude […]

Prompts and Videos from Estate Planning Webinar

Today I spoke with Jeffrey Bowley, CPA, MT at the Bucks County Estate Planning Council about AI. In our slides I included several prompts and videos. I promised the attendees I would upload the videos from the class. Ethical Billing Review in Claude This first video was not in my slide deck, but I thought […]

Two Courts, Two Answers: When Does Using AI Waive Privilege?

On the same day in February 2026, two federal courts looked at AI and privilege and came to opposite conclusions. The question both addressed matters to every lawyer using artificial intelligence: does putting information into an AI tool waive privilege? The answer depends on which courtroom you are in, and, in this author’s opinion, on […]

AI Handoff Checklist: Know When to Start Fresh & What to Capture

You are working with an AI. The model understands your constraints, your tone, the decisions you have already made. Then something shifts. Responses become generic. Settled issues get reopened. The thread feels thinner. You have likely hit the edge of the context window. Every AI model can only process a finite amount of text at […]

AI Context Window: Guide to Long Conversations & Handoff Documents

Try the Interactive AI Handoff Checklist You are deep into a conversation with Claude. You have spent the last hour shaping a proposal, debugging a stubborn issue, or building something iteratively. The model understands your tone, your constraints, and the decisions already made. Then something shifts. The responses become slightly generic. Issues you resolved earlier […]

Claude AI Privilege Waiver: What U.S. v. Heppner Means for Your Clients

Download a Sample Client AI Confidentiality Notice Every few months we see a headline suggesting that artificial intelligence has upended some settled area of law. It usually hasn’t. More often, a court simply applies existing doctrine to a new tool and reaches the same result it would have reached twenty years ago with email, Google, […]

Moltbook, AI Agents, and What Lawyers Actually Owe Clients

Over the past several weeks, a familiar cycle has played out in the technology press. Headlines claim that “AI agents” have created their own social media network, are chatting with one another, forming religions, and, in some versions of the story, even contemplating humanity’s fate. The platform at the center of much of this attention […]