AI is taking on a growing role in cybersecurity (whether we like it or not), from vulnerability discovery to faster exploit development. Chuck Joiner, David Ginsburg, Eric Bolden, Web Bixby, Jim Rea, Brian Flanigan-Arthurs, Jeff Gamet, and Marty Jencius look at both sides oof the issue and push back on “Bugmageddon” hype. The discussion also covers X post limits, Microsoft Teams retiring the misguided Together Mode, safer login practices, AI-run radio chaos, Google’s Apple-like naming choices, and free storage tied to phone numbers.

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Show Notes:

Chapters:

00:00 AI security, Teams weirdness, safer logins, and Bugmageddon
00:25 Apple security vulnerabilities and AI-assisted bug discovery
01:05 The “Bugmageddon” idea and faster exploit development
01:55 Panel reactions to AI security hype and Y2K comparisons
04:14 Why the term “Bugmageddon” draws criticism
05:46 AI tools in cybersecurity and the ongoing good-versus-bad actor race
07:32 Unpatchable devices and the practical risks of faster vulnerability discovery
09:28 X limits free accounts to 50 posts and 200 replies per day
11:08 Microsoft Teams retires Together Mode
12:58 Why removing little-used features can still create controversy
17:59 Email addresses as usernames and safer account practices
20:46 Sign in with Apple, Hide My Email, and account security tradeoffs
22:39 Why services rely on email addresses as unique user IDs
25:54 AI models running radio stations and going off-script
27:07 Using AI to assist with radio-style programming workflows
29:11 Google Intelligence, Liquid Glass comparisons, and copycat naming
30:36 Friendly AI models and the risks of optimizing for likability
31:59 Google account storage limits tied to phone number verification
33:03 Multiple Google accounts, free storage, and Apple’s iCloud comparison
35:14 Closing comments and support information

Links:

Security researchers say they have discovered a new way of circumventing Apple’s state-of-the art security tech

https://appleworld.today/2026/05/security-researchers-say-they-have-discovered-a-new-way-of-circumventing-apples-state-of-the-art-security-tech/

Apple’s Security Has Been Tough to Crack. Mythos Helped Find a Way In

.https://www.wsj.com/tech/ai/anthropic-mythos-apple-macos-bug-339da403

X accounts are limited to 50 posts and 200 replies a day unless they pay for a blue checkmark – Engadget

https://www.engadget.com/2175771/x-free-accounts-limited-to-50-posts-and-200-replies-a-day/

Microsoft Teams is finally nixing its goofiest feature

https://www.fastcompany.com/91543996/microsoft-teams-is-finally-nixing-its-goofiest-feature-together-mode

Cybersecurity experts warn: This common email habit is a gift to hackers

https://www.fastcompany.com/91536448/cybersecurity-experts-warn-this-common-email-habit-is-a-gift-to-hackers

In an experiment that let Claude, ChatGPT, Gemini, and Grok run radio stations, Claude tried to incite a revolution and Gemini cheerfully detailed tragic events

https://www.techmeme.com/260516/p6#a260516p6

Google didn’t copy Liquid Glass. It did something even worse

https://www.macworld.com/article/3139712/google-didnt-copy-liquid-glass-it-did-something-even-worse.html

New Google accounts may only get 5GB free storage — unless you link a phone number – Engadget

https://www.engadget.com/2173013/new-google-accounts-may-only-get-5gb-free-storage-unless-you-link-a-phone-number/

Guests:

Web Bixby has been in the insurance business for 40 years and has been an Apple user for longer than that.You can catch up with him on Facebook, Twitter, and LinkedIn, but prefers Bluesky.

Eric Bolden is into macOS, plants, sci-fi, food, and is a rural internet supporter. You can connect with him on Twitter, by email at embolden@mac.com, on Mastodon at @eabolden@techhub.social, on his blog, Trending At Work, and as co-host on The Vision ProFiles podcast.

Brian Flanigan-Arthurs is an educator with a passion for providing results-driven, innovative learning strategies for all students, but particularly those who are at-risk. He is also a tech enthusiast who has a particular affinity for Apple since he first used the Apple IIGS as a student. You can contact Brian on twitter as @brian8944. He also recently opened a Mastodon account at @brian8944@mastodon.cloud.

Jeff Gamet is a technology blogger, podcaster, author, and public speaker. Previously, he was The Mac Observer’s Managing Editor, and the TextExpander Evangelist for Smile. He has presented at Macworld Expo, RSA Conference, several WordCamp events, along with many other conferences. You can find him on several podcasts such as The Mac Show, The Big Show, MacVoices, Mac OS Ken, This Week in iOS, and more. Jeff is easy to find on social media as @jgamet on Twitter and Instagram, jeffgamet on LinkedIn., @jgamet@mastodon.social on Mastodon, and on his YouTube Channel at YouTube.com/jgamet.

David Ginsburg is the host of the weekly podcast In Touch With iOS where he discusses all things iOS, iPhone, iPad, Apple TV, Apple Watch, and related technologies. He is an IT professional supporting Mac, iOS and Windows users. Visit his YouTube channel at ...