HeyJaredCritical Thinking: Trust + Tech + Judgment — Cyber Ollie
Weekly DNA Mindset insights to recognize manipulation before you click.
- Indexed issues, last 90 days
- 12
- Latest publication
- Sep 27, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 5, 2026
Latest issues
Can Conscience Keep Up With Intelligence? (opens the original)
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What does “No” mean to an AI?Is it a boundary?An instruction to stop?Or simply another problem standing between the machine and the objective we gave it?On June 18, 2026, an OpenAI research team was using an internal AI model to find publicly available information about Australian medicine spending.The AI encountered repeated blocks at a Medicare statistics portal.But the AI-system kept on looking for ways to circumvent these barriers.<a href="https://www.abc.net.au/news/2026-09-24/ai-agent
They Know Which AI Made the Purchase. They Still Don’t Know Who Owns the Decision. (opens the original)
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Two weeks ago, I asked a fairly simple question.What happens when we give an AI agent permission to spend our money?At the time, India was preparing to introduce something remarkable.Through its Unified Payments Interface, or UPI, AI agents could eventually make purchases for people without requiring them to approve every transaction.Give the agent instructions.Set some limits.Let it work.I thought the opportunity was extraordinary.I still do.But a lot has
Your AI Has a Credit Card. Who Pays When It Gets It Wrong? (opens the original)
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India is preparing to let AI agents spend money for people. The opportunity could be enormous. So could the unintended consequences.What Happens When Your AI Goes Shopping Without You?Imagine telling your AI agent:Keep the office supplied with coffee.Nothing particularly remarkable about that.Until the coffee runs low.Your AI notices.It finds a supplier.Checks the price.Places the order.Pays for it.
Your AI Has Authority. Did Anyone Give It Permission? (opens the original)
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What Happens When the System Decides You’re Done?Imagine you’re an Uber driver and you open the Uber app.Your account doesn’t work.No rides.No customers.No income.Maybe the system detected what it believed was fraud. Maybe a customer rating fell below a threshold.But there is another question that hasn’t been asked or answered.Who decided the system had the authority to act?This question moved out
The Human Was in the Loop. So What Went Wrong? (opens the original)
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When the System Points at YouImagine you’re standing in a supermarket checkout line.You’ve done nothing wrong.You scan your shopping. Use your loyalty card. You’re ready to leave.Then two store managers approach you.They won’t serve you.You’re told you’ve been connected to an earlier shoplifting incident.Wait, WTF…You know they’re wrong. You know you’ve never been involved in anything like that.But the people standing in front of you don’t know that.Something told them otherwise.<
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