Reassurance Loops and Why AI Can Quietly Undermine Judgment
One of the most subtle risks in working with AI has nothing to do with hallucinations, data breaches, or outright errors. It has to do with reassurance. People often describe AI as persuasive or authoritative, but that is not quite right. What AI does exceptionally well is friction reduction. It smooths uncertainty. It makes a […]
The Quiet Automation of Healthcare
I recently went to Jefferson to see my doctor. It was a doctor I don’t need to see very often, and I had not visited her for several years. When I spoke to the person to set up the appointment, she told me that the office had moved. When I arrived, I was immediately impressed […]
What the AIs Said About Themselves: A Lawyer’s Guide to AI “Self-Reporting” on Privacy
Over the past several weeks, I have been writing about each of the major AIs. I asked each of them the same thing: I am writing a blog post for attorneys on what they should know about what attorneys should know about you, that is [name of ai] so they can be aware of what […]
Copilot Is Not One Tool: It Is Four Distinct Environments
Lawyers often talk about “Copilot” as if it is a single tool. It is not. Microsoft uses the same name across multiple products that behave very differently from a confidentiality and governance standpoint. For lawyers, the meaningful dividing line is whether Copilot is operating inside your organization’s Microsoft 365 tenant or outside it. Everything else […]
Perplexity and Privacy: What Its “Low Footprint” Model Really Means
Perplexity AI often presents itself as a more privacy-respectful alternative to large platform AI tools. And in some respects, that is true. But as with every AI platform, the real answer is not “private” or “not private.” The answer is “it depends.” This post explains what Perplexity’s privacy posture actually looks like in practice and […]
Gemini and Privacy: What Google’s AI Actually Does With Your Data
If you are using Gemini, Google’s AI assistant, you are probably asking the same question people are asking about every AI tool. Is my data private. The real answer is not yes or no. It depends. It depends on which account you are using.It depends on how your settings are configured.It depends on whether you […]
Website Security Isn’t Just Plugins: What Actually Protects Your Site
When people talk about website security, the conversation usually starts and ends with passwords and plugins. Strong password. Install a security plugin. Turn on two-factor authentication. All of that is fine. It is also incomplete. Real website security is architectural. It is about how your site is structured, where it lives, who controls what, and […]
Claude and Privacy: What Lawyers (and Everyone Else) Should Actually Understand
Claude and Privacy: What Lawyers and Everyone Else Should Actually Understand If you are using Claude, Anthropic’s AI assistant, you probably want to know whether your conversations are private. The answer is: it depends. It depends on which type of account you have.It depends on when you created that account.It depends on what settings you […]