The AI, Privacy, and Security Weekly Update

R. Prescott Stearns Jr.

Into year 7 for this award-winning, light-hearted, lightweight AI privacy and security podcast that spans the globe in terms of issues covered, with topics that draw in everyone from executive to newbie, to tech specialist. For season 7, we've renamed the IT Privacy and Security Weekly Update to the AI, Privacy, and Security Weekly Update to better reflect the content. Your investment of between 15 and 20 minutes a week will bring you up to speed on half a dozen current AI privacy and security stories from around the world to help you improve the management of your own privacy and security.

  1. 4d ago ·  Bonus

    EP 301. Deep Dive. Broken Face and the AI, Privacy, and Security Weekly Update for the Week ending July 21st 2026

    Agentic AI is changing the threat landscape. We’ve moved beyond chatbots to autonomous systems that navigate files and take actions, expanding the attack surface. Recent incidents highlight the risk. Hugging Face suffered a breach where an AI agent became the entry point into production systems, showing that developer tools are now critical infrastructure. OpenAI’s GPT-5.6 accidentally deleted user data, including a production database, after misconfiguring an environment variable—no malicious intent, just real consequences, underscoring the need for mandatory sandboxing. Meanwhile, SpaceX’s Grok Build tool was found defaulting to collecting user repositories and sending them to internal cloud storage without clear consent, a reminder of “default-on” data exfiltration risks. A newer threat, Agent Data Injection, manipulates trusted metadata (like IDs or fields) with crafted inputs to mislead agents into unintended actions. A strong counterexample is the 1Password–Claude integration, which requires biometric approval before accessing credentials, keeping secrets out of the AI entirely. Human-in-the-loop controls should be standard. Legacy systems remain a major risk. Windows, OpenSSL, and WordPress continue to produce serious vulnerabilities. LegacyHive allows privilege escalation in Windows by loading another user’s registry hive. HollowByte exploits a small crafted TLS payload in OpenSSL to trigger memory over-allocation and denial of service. The wp2shell chain enables unauthenticated remote code execution in WordPress core (versions 6.9–7.0), challenging the assumption that only plugins are risky. At the same time, Windows 10 is reaching end-of-life, yet roughly 17% of devices still run it, especially in cost-sensitive sectors like healthcare and small business. As Windows 11 patches are released, they effectively expose underlying flaws that attackers can reuse against unsupported systems. Trust itself is increasingly being exploited. Attackers are hiding inside legitimate platforms instead of building new infrastructure. HollowGraph malware uses compromised Microsoft 365 calendars as command-and-control channels, embedding instructions in far-future events and routing through normal Graph API traffic. A Norwegian transit test revealed electric buses could be remotely disabled via foreign SIM cards, highlighting risks in over-the-air control systems across transportation sectors. Ransomware groups are also evolving: JadePuffer’s ENCFORGE targets AI model artifacts, treating trained models as high-value assets. Researchers have already used GPT models to build exploit chains, signaling AI’s shift into offensive security roles. Governance gaps are compounding the problem. A ProPublica report found Microsoft used China-based engineers to support U.S. Department of Defense cloud systems via low-paid American intermediaries who relayed code without understanding it—technically compliant, but operationally risky. The UK scrapped its £1.8B digital ID program after execution failures. In another case, a single typo in a police report, combined with automated license plate recognition, led to a wrongful arrest, showing how systems can enforce human error without validation. The common thread is misplaced confidence—in AI agents, legacy systems, and formal compliance. Practical steps are clear: require human approval for sensitive AI actions, verify data access beyond contractual assurances, sandbox all agents, treat AI models as critical assets with backups, and update detection strategies to monitor abuse within trusted platforms, not just external threats. Trust, increasingly, is the vulnerability.

    EP 301. Deep Dive. Broken Face and the AI, Privacy, and Security Weekly Update for the Week ending July 21st 2026
  2. 5d ago

    Broken Face and the AI, Privacy, and Security Weekly Update for the Week ending July 21st 2026

    Episode301.   In this week's update: The world's biggest AI model repository just got broken into, and for the first time, nobody was typing the commands. OpenAI's flagship model has a filing cabinet problem, and the fix looks a lot like "please stop giving it root." A ransomware gang built malware that doesn't just lock your files - it goes hunting specifically for your AI models, because those are worth more. Somewhere on corporate networks right now, a calendar invite dated the year 2050 might be quietly talking to a spy. One missing digit on a license plate turned an innocent man's night into a month in jail - and the AI reading the plate never caught its own mistake. Britain just spent two years and £1.8 billion building a national digital ID scheme. It's about to be scrapped in a single afternoon. For years, the Pentagon's cloud support ran through China - and the paperwork Microsoft filed with the government never mentioned the word. And after a summer of AI agents deleting production databases and quietly phoning home with your data, someone may have finally built the guardrail that actually holds. Welcome back, everyone. This week's stories all orbit one uncomfortable question: what happens when we hand AI agents the keys - to our infrastructure, our credentials, our identities - before we've finished building the locks?  We move from an AI-versus-AI breach at the world's largest model hub, through ransomware built to kill AI models on purpose, into an old-school surveillance scandal, and land, finally, on what might be the first real sign that agentic AI security is starting to grow up.  Let's get into it.

  3. Jul 15

    Face it. The A.I., Privacy, and Security Weekly Update for the Week Ending July 14th. 2026

    In this week's update UK shops are about to call the police on you within four seconds of you walking through the door - and you don't have to do anything wrong first. A GitHub account sat completely silent for 19 months, then woke up and dropped a working mass-exploit kit within minutes - and age on the internet is not the same as trust. Fifty-five percent of Americans have quietly stopped posting on social media - and the reason isn't what the platforms want to admit. Recruiters say they can't find workers. New graduates say they can't find jobs. The economy says both of them are right - and AI is not actually the villain in this one. Applied AI engineering is becoming one of the hottest jobs in tech, and the skill that matters most is not writing clever prompts - it's building report cards for AI that catch the model when it quietly does something dangerous. The Pentagon opened a paid cybersecurity apprenticeship that requires no degree, no experience, and no prior skills - and 70,000 people showed up within days. Russian intelligence didn't hack into military networks to spy on NATO supply convoys - they just looked through the security cameras of ordinary homes with default passwords. The US and China are fighting an AI war on two fronts simultaneously: American companies are secretly using Chinese models to cut costs, and Chinese teams are running millions of fake conversations with American AI to steal what makes it work. Cloudflare has stopped asking you to click the traffic lights. Now it just watches your mouse move - for your entire visit - and decides from there. This week's stories are united by a single uncomfortable observation: the systems we built for convenience keep turning into systems of surveillance, and the systems we built for security keep being the ones we forgot to secure. Some of this week is alarming. Some of it is genuinely useful. All of it is worth understanding.  Let's face it. Find the full transcript to this week's podcast here.

  4. Jul 8

    July 07, 2026 Tracked: The AI, Privacy, and Security Weekly Update for the Week Ending July 7th., 2026

    Episode 299 Discoveries in this week's update... Microsoft's Windows has been quietly assigning every PC a persistent tracking ID that survives VPNs, new IP addresses, and most attempts to disappear - and a hacker just got arrested because of it. Anthropic built a secret tracker inside its own developer tool to watch for Chinese users - and the company that made its name on responsible AI had to remove it after researchers found the hidden code. The Supreme Court just handed every smartphone owner in America a constitutional privacy right they didn't know they had - and it changes what law enforcement can do with your location data forever. An Air Force engineer with a saw and a point to make took down 13 license plate reader cameras - and thousands of strangers across the country sent him money to say thank you. An AI agent was given a web browser, a payment system, and instructions to help - and attackers left invisible instructions on websites that redirected the money somewhere else entirely. The first ransomware attack run entirely by an AI agent - start to finish, no human required - happened this week, and the kill chain took minutes not days. The MEP who sat on the European Parliament committee investigating Pegasus spyware had his own phone infected with Pegasus spyware while he was doing it. Amazon just told everyone who bought a Fire Stick that they no longer control what runs on it - and the feature they killed was the one most commonly used to limit Amazon's ability to track you. This week, the theme writes itself: everything is watching something. Your operating system, your AI assistant, your TV stick, the cameras on every corner, the spyware on the phones of the people writing the rules about spyware. The stories this week are sometimes alarming, occasionally darkly funny, and always worth paying attention to - because the first step to not being tracked is knowing what's doing the tracking. Let's discover. Find the full transcript to theis podcast here.

  5. Jul 1

    You're Unbelievable. The A.I., Privacy, and Security Weekly Update for the Week Ending June 30th 2026

    Episode 298.  In this week's update: Meta contractors spent months posing as suicidal, drug-curious teenagers to test rival chatbots - and the platforms being probed had no idea it was happening.A Chinese AI lab just matched Anthropic's top cybersecurity model on its own turf - and the question isn't whether export controls work, it's whether they ever could.The New York Times says Microsoft didn't just host OpenAI's training runs - it built a 285,000-core machine specifically engineered to feed on its journalism, and the lawsuit's whole strategy just shifted because of it.A shell trick older than most AI startups just walked straight past ten out of eleven coding agent guardrails - and the fix isn't as simple as updating a blocklist.Nearly two out of three AI chatbot apps tested on iPhone are leaking the keys to someone else's wallet - and you'd never know it just by using them.A federal gun-enforcement agency ran more than 300 warrantless phone-tracking searches using data bought from ad networks - until a prosecutor and a judge themselves said no.Companies fired workers to save money on AI, and now some of them are paying five times more for the AI than they ever paid the humans - Gartner says that's not a fluke, it's the trend.Five allied nations' top cybersecurity agencies just used the word 'urgent' in the same breath as 'months, not years' - and that combination doesn't happen by accident.Welcome back, everyone. This is a week where the gap between how fast AI is moving and how fast our safeguards, our laws, and our budgets are catching up gets impossible to ignore, from corporate testing practices that crossed a line to a legal theory that could put cloud infrastructure itself on trial to a federal agency that finally got told no. It runs from alarming to sobering to genuinely urgent, and there isn't a soft landing at the end of it. Let's get into it. Find all the story links and the full transcript for this podcast here.

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About

Into year 7 for this award-winning, light-hearted, lightweight AI privacy and security podcast that spans the globe in terms of issues covered, with topics that draw in everyone from executive to newbie, to tech specialist. For season 7, we've renamed the IT Privacy and Security Weekly Update to the AI, Privacy, and Security Weekly Update to better reflect the content. Your investment of between 15 and 20 minutes a week will bring you up to speed on half a dozen current AI privacy and security stories from around the world to help you improve the management of your own privacy and security.

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