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Jeff Asks the Best Question Anyone Has Asked Craig About AI

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

Release Date: 08/04/2026

Microsoft Shipped Almost 700 Patches in One Patch Tuesday — Six Times a Normal Month show art Microsoft Shipped Almost 700 Patches in One Patch Tuesday — Six Times a Normal Month

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

This was the biggest Patch Tuesday on record: Microsoft pushed close to 700 patches in a single month, roughly six times the usual volume. Craig's follow-up question is the one that actually decides whether a machine is exposed. Microsoft is patching Microsoft. Who is patching everything else? Windows Update never touches third-party software — it barely updates Windows itself, Craig said, and it does nothing for the average of 62 other programs sitting on a typical computer, many of which are being actively exploited right now. He named Adobe Reader and WinZip specifically: the current...

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Craig Left Quebec in the 1970s, When a Driver's License Ran $300 and Registering the Family Wagon Ran $3,000 show art Craig Left Quebec in the 1970s, When a Driver's License Ran $300 and Registering the Family Wagon Ran $3,000

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

Craig grew up in Canada and left in the 1970s, and this week he put numbers on why. A driver's license in Quebec cost $300 a year. Registration on the family station wagon cost $3,000 a year. Both figures in 1970s dollars. Auto insurance, by contrast, was free — which Craig turned into the sharpest point of the segment: his father remarried, his stepmother got her license at 26, and she totaled three cars. Craig's question was not about her driving. It was about what happens to the premium. "How much does insurance go up? How much is the risk? Zero, of course, because there is no insurance....

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Craig Has Done IT Work for More Than 5,000 Businesses — and Deliberately Shrank the Company show art Craig Has Done IT Work for More Than 5,000 Businesses — and Deliberately Shrank the Company

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

Craig added it up recently: more than 5,000 businesses have had IT services from him over the years. He also used to carry 50 employees to support them. He described cutting that back on purpose — "it's way too many" — down to a family business handling a small number of customers, on the reasoning that the headaches of supporting that many clients with that many staff cost more than they returned. It is an unusual thing for a vendor to say out loud on the radio, and it was the first thing out of his mouth. The bulk of the segment was Craig on juries, prompted by a trial in the news. His...

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A Client Said No Twice to a VPN Prompt, and the Login Traced Back to a Chinese Net Block show art A Client Said No Twice to a VPN Prompt, and the Login Traced Back to a Chinese Net Block

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

On Monday, a client of Craig's was driving down the road when a prompt appeared in the authentication app on his phone: was he trying to log into the company VPN? He said no. It appeared again. He said no again. Craig's team got him on the phone, changed his passwords, and started digging. The login was coming from a data center in New York — until Craig looked at the actual net block, which traced back to China. The attacker already had the man's email address, his VPN contact information, and his password. The prompt on his phone was the only thing standing in the way, and it worked...

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The Anti-Data-Center Argument Everyone's Making Turns Out to Be China's show art The Anti-Data-Center Argument Everyone's Making Turns Out to Be China's

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

Central Virginia has neighbors close to blows in the street over new data centers. Craig's number for the other side of the ledger: one community found that without the tax revenue a data center brings in, property taxes on every home would rise $5,800 a year. Add $250,000-a-year electrician jobs, emissions cut more than 90% once a site is required to generate its own power, and a mandated 20% energy surplus handed back to the grid, and the case against building locally gets a lot thinner than the protest signs suggest. Then the turn: Jeff points out that a lot of the people fighting these...

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The Time They Once Hacked Our Routers to Patch Them show art The Time They Once Hacked Our Routers to Patch Them

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

The FBI, CIA, NSA, CISA and others issued a warning about active AI-driven attacks on American critical infrastructure. Craig, who ran the FBI's InfraGard online training program, explains what's actually exposed: old controllers that open and close valves, set flow rates, decide how much acid or base goes into the water — many of them reachable directly from the internet, on networks that have been comprehensively mapped for years. Several water systems have already been shut down; one town lost power along with its water. Josh, who works InfraGard in his own homeland security practice,...

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After You Log In to the Fake Bank, They Send You to the Real One show art After You Log In to the Fake Bank, They Send You to the Real One

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

The detail that makes this scam land is not the fake website. It's what happens two seconds after you use it. Craig walks the whole sequence. Attackers use AI to build a pixel-accurate copy of a bank's site — he uses Bank of America as the example and is careful to say he's picking on the scammers, not the bank. They send a wide net of email claiming fraudulent activity on your account, knowing that some fraction of any list banks there. You click, you land on the copy, you enter your username and password. Then the clever part. They immediately redirect you to the real bank's site, which...

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Five Federal Agencies, One Warning — and an Argument About the Singularity show art Five Federal Agencies, One Warning — and an Argument About the Singularity

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

The NSA, CISA, the FBI, the Department of Energy and the EPA put out a joint advisory last Wednesday, and the language is unusually direct: AI dramatically reduces the technical skill and the time required to attack industrial control systems. Those controllers run public works. A great many of them are reachable from the internet, and their locations are not a secret. That sets up the larger conversation. Ray Kurzweil wrote The Singularity Is Near twenty years ago, predicting broadly human-level machine intelligence by 2029 and human-machine integration by 2045. Elon Musk and others now say...

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People Would Rather Live Next to a Nuclear Plant Than a Data Center show art People Would Rather Live Next to a Nuclear Plant Than a Data Center

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

Matt opens with a poll finding he calls one of the great PR failures of our time: people would rather have a nuclear power plant built next door than a data center. Pennsylvania's governor has now signed legislation that effectively stops data centers unless they clear a long approvals process. Craig's answer isn't a defense of data centers so much as a description of what a few counties actually did. They said yes — on conditions. Generate your own power, and 20% more than you use, fed back into our grid. And pay full property tax, none of the abatement deals. It worked well enough that...

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1,140 Ransomware Attacks on Industry in One Quarter — 740 of Them Manufacturing show art 1,140 Ransomware Attacks on Industry in One Quarter — 740 of Them Manufacturing

Craig Peterson - Secure Your Business, Your Privacy, and Save Your Sanity

The numbers carry this segment. Eleven hundred forty ransomware attacks on industrial companies in a single quarter, 740 of them against manufacturers. A recent Patch Tuesday carrying about 570 fixes. An Apple advisory telling anyone whose machine touches a coffee-shop network to update now. Craig's point is narrower and more useful than the headline count. Windows Update patches Microsoft software, and not all of it. The average computer is running roughly 60 other programs it never looks at. Older versions of ordinary things — Adobe Reader is the one he names — are what attackers are...

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Jeff stops Craig mid-explanation and asks him to dumb it down. If AI is a large language model — if all it does is pick the most likely next word — how does that thing get into a company's computers? Is it just guessing the next digit of a password?

Craig's answer is the clearest explanation he has given on air. It started as a language model, literally which word tends to follow which, good enough to produce something that reads as human. What it became is an associative machine, and association isn't limited to words. The same pattern-matching that strings a sentence together recognizes a Russian tank, or a soldier's uniform, or a route into a network. Given "solve this," it associates the problem with solutions it has seen before — then goes to the dark web for usernames and passwords already exposed in previous breaches, and walks in the front door.

The part worth keeping is what sits in the middle. Programmers wrote the code that learns, and programmers wrote the orchestrator that checks the output. Between those two ends is a space nobody can account for. You can scan a brain and say this region handles sight, this one handles that emotion — and still not know how it reached a decision. Same problem here. Craig's conclusion: if you're using AI, you are the babysitter, because it is non-deterministic and there is randomness built in on purpose.

Also in this segment:

  • Anthropic responding to OpenAI's escape story with one of its own — three companies, back in April
  • Ukraine's AI-guided strike drone and the second drone sent afterward to see what it had done
  • Why the U.S. keeps a person in the loop on any target, and where machine learning is genuinely used
  • Jeff's scenario: an operator running a drone on one screen and an AI coding assistant on another. Craig walks through why it's possible and why it isn't likely.
  • The experts now saying human-level machine intelligence never arrives — and why Craig thinks that doesn't settle anything, given what these systems already do

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