A few weeks ago, I was wrestling with a major life decision. Like I’ve grown used to doing, I opened Claude and started thinking out loud-laying out the options, weighing the tradeoffs, asking for perspective.

Midway through the conversation, I paused. I realized how much I’d shared: not just this decision, but months of conversations-personal dilemmas, health questions, financial details, work frustrations, things I hadn’t told anyone else. I’d developed a level of candor with my AI assistant that I don’t have with most people in my life.

And then an uncomfortable thought: what if someone was reading all of this?

The thought didn’t let go. As a security researcher, I have the tools to answer that question.

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