TEH 269: Exploring Apple’s AI Upgrades and the Changing Landscape of Online Search
In This Episode:
Exploring Apple’s AI Upgrades and the Changing Landscape of Online Search
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
Our guest is …
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 GR: Apple WWDC (World Wide Developer Conference)
They’ve largely stopped talking about each OS separately
2:25 Golden Gate
4:50 Not liking liquid glass. Rollback on design a bit
6:00 Focus on speed and reaction times
7:50 “Siri AI”
Functional AI: Safari tabs, custom Safari extensions, Photo extend/reframe, build a Shortcut, act on files
12:50 Safari Notify me
16:00 Photos
19:20 Shortcuts
22:40 AI privacy
25:00 Splintering of OS features: US, EU, China.
30:00 Release dates
31:20 LN: AI search
Google’s announcement:
https://blog.google/products-and-platforms/products/search/search-io-2026/
34:00 Switching to ChatGPT
35:50 Kagi
37:00 Control with a question mark
40:40 Results depend on how you phrase your question
41:45 Semi-related: Better search customization coming in Windows 11 (i.e. no Bing, no Store) –
https://hothardware.com/news/windows-11-disable-bing-search-single-toggle
Ain’t it Cool
43:10 GR: Hacks series finale
44:50 LN: World of Warcraft
BSP: Blatant Self-Promotion
46:20 LN: You Can’t Un-Ring a Bell: What Really Happens to Your Data When You Post Anything Online – https://askleo.com/24288
47:50 GR: https://macmost.com/3-ways-to-keep-icloud-files-and-photos-local.html
Transcript
teh_269
Video
https://youtu.be/PEr1RMD3EaA
June 3, 20261 hr 3 min
TEH 268: Airline Bluetooth Scare. Understanding the Cloud. Is AI Creepy?
In This Episode: Airline Bluetooth Scare. Understanding the Cloud. Is AI Creepy?
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 GR: Police department’s social media tactics lead to arrests — and criticism
https://vtdigger.org/2026/05/21/police-departments-social-media-tactics-lead-to-arrests-and-criticism/
(“The online attention can have long-lasting consequences for those named in the posts”)
GR: Reserecting Vine
https://techcrunch.com/2025/11/12/jack-dorsey-funds-divine-a-vine-reboot-that-includes-vines-video-archive/
7:00 LN: Neo competitors arrive.
Microsoft’s surface laptop ultra – https://www.microsoft.com/en-us/surface/devices/surface-laptop-ultra
https://www.howtogeek.com/nvidia-rtx-spark-laptops-are-doomed-to-fail-heres-why/
Nvidia chip based (ARM) – doomed IMO
GR: https://www.macrumors.com/2026/06/02/macbook-neo-outsold-every-other-mac/
14:00 GR: Plane turned around with bluetooth device name
https://apnews.com/article/united-flight-newark-spain-bluetooth-device-ccdd9c111084ca0b8f5127f1baa74465
29:00 LN: Cloud Storage, Objections, and a great AI use case
Can cloud services see your data?
Do cloud services use your data?
Do cloud services own your data?
45:00 GR: Asking AI to do something and then being creeped out that it did it well
https://www.theverge.com/ai-artificial-intelligence/941388/gemini-spark-ai-agent-trip-planning
50:00 GR: Guess you didn’t escape the “subscription” after all
https://www.macrumors.com/2026/06/02/microsoft-office-2019-for-mac-no-edit-documents/
Ain’t it Cool
55:00 LN: Eupohoria
56:00 GR: Boys Series finale
BSP: Blatant Self-Promotion
1:01:00 LN: Mythos About Mythos – https://askleo.com/192235
1:02:00 GR: https://macmost.com/7-skills-you-need-to-master-mac-pages.html
Transcript
teh_268
Video
https://youtu.be/3p3G94fTSjE
May 21, 20261 hr 5 min
TEH 267: Apple’s AI, Google I/O Updates, and the BitLocker Yellow Key Security Flaw
In This Episode: Apple’s AI, Google I/O Updates, and the BitLocker Yellow Key Security Flaw
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 GR: What will the new Siri be like? (WWDC coming up)
Stand-alone app
Voice assistant that understands what you mean
Gemini but not Gemini, Gemini model running on Apple’s servers, doing Apple things
12:30 LN: Bitlocker busted?
Yellowkey exploit
16:00 How encryption keys are really stored
22:00 GR: Folding Phones?
Big deal or niche product?
Really looks like Apple is doing this soon (iPhone Ultra)
Pixel Fold: https://store.google.com/product/pixel_10_pro_fold?hl=en-US&pli=1
33:00 GR: Google I/O stuff, audio glasses, AI agents
Glasses without any visual component: just mic, speaker and camera?
36:00 LN: https://bee.computer/
41:00 Hot take: People don’t want agents, as people don’t normally have assistants. Normal people talk to other people (chat)
Also: Could it come to a point where it is all just moving too fast?
Ain’t it Cool
57:00 GR: I’ll Miss Stephen Colbert
1:00:00 LN: New Murderbot – Platform Decay
BSP: Blatant Self-Promotion
01:01:16 GR: https://macmost.com/10-reasons-why-you-should-be-using-icloud-photos.html
01:03:43 LR: Has BitLocker Been Broken? What YellowKey Means to You – askleo.com/192620
Transcript
teh_267
Video
May 6, 20261 hr 8 min
TEH 266: Are you an AI? Robot music… is it good or bad? Ditching VPN and saving photos.
In This Episode: Are you an AI? Robot music… is it good or bad? Ditching VPN and saving photos.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
3:08 LN: “How Do I Know You’re Not AI?” – Article coming up “tomorrow” as we record this.
A problem that’s only going to get “worse”, for some definition of worse
As things improve, will it matter? Good content is good content regardless of the source, right?
7:00 GR: Starting to suspect PR pitches are using a lot of AI
Every one now starts with flattery
Suggestions can be totally of the wall
12:00 GR: AI Music
Needed music, Suno was easy and “safe”
What are the alternatives?
Music without soul? Or, not all art needs to be Art.
15:00 Link to video montage: https://vimeo.com/1187110569/1742b3aeb4
Cain Walker: https://www.youtube.com/@CainWalkerMusic real or AI?
27:00 LN: Anthropic’s Mythos: hype or legit concern?
Pronunciation controversy? 😏
Supposedly extra good at identifying vulnerabilities
“We have identified thousands of additional high- and critical-severity vulnerabilities that we are working on responsibly disclosing to open source maintainers and closed source vendors.”
Just as good at fixing?
Project “glasswing” – a select few, but you know it’ll get out
Not targeted at vulnerability detection, just a Really Good Model that happens to do this well. What else will it do well?
30:00 Is this the future of AI Model releases?
Assessing Claude Mythos Preview’s cybersecurity capabilities – Anthropic
Anthropic’s Claude Mythos Finds Thousands of Zero-Day Flaws Across Major Systems – Hacker News
37:00 GR: Ditching VPN
I’m done wasting my vacation time
46:00 LN: Didn’t work in the hospital either
47:00 GR: Travel: Real camera kept winning
Big sensor, big glass, viewfinder, but also mindfulness
54:00 Dehazing… How I saved Machu Picchu
Ain’t it Cool
58:00 LN: The Boys – not for the faint of heart, but fascinating, and the subtle and not-so-subbtle digs to current events are great. (Daredevil also.)
59:00 GR: “Apple: The First 50 Years” by David Pogue
BSP: Blatant Self-Promotion
1:01:00 LN: How Do I Know You’re Not AI? – https://askleo.com/191783
1:02:00 GR: 10 Weird macOS Features That Are Somewhat Useful (2026)
Transcript
teh_266
Machu Picchu
Machu Picchu as shot. Click for larger image.
Machu Picchu after “dehaze” applied. Click for larger image.
Video
https://youtu.be/xqu_aV429rA
April 9, 20261 hr 2 min
TEH 265: What Happens to Ask Leo and MacMost as AI Evolves? When we first touched computers.
In This Episode: What Happens to Ask Leo and MacMost as AI Evolves? When we first touched computers.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
00:00 GR & LN: How can Ask Leo and MacMost change to survive the AI future?
LN: not uncommon for me to take a question I’ve been asked and plop it into Claude and get a decent answer. (Updated example at How I Use AI at Ask Leo!)
What does this mean for tech support future?
06:58 Challenges with AI content accuracy
GR: Still a lot of hallucinating, and not understanding old vs new, and too much agreeing with the asker.
Dealing with lists
People don’t know how to ask the questions
14:53 AI limitations in suggesting and automating tasks
It won’t correct you when it should
17:32 Asking AI to clarify terminology
Phrasing questions right
Pointing people in a new direction. Educating about new stuff.
We do demonstrations of details.
26:05 Planning for a future pivot in tech support
27:34 GR: “I don’t have to run faster than the bear, I just need to run faster than you.”
34:43 Automating log checks with Claude
39:49 Learning to code and problem-solving with AI
45:40 Talking about the old Mac Pro
Not openable and fixable
50:00 When I first touched a computer
Ain’t it Cool
52:00 GR: Project Hail Mary
57:00 LN: QI – (Quite Interesting – BBC / Amazon Prime Britbox)
BSP: Blatant Self-Promotion
59:00 GR: https://macmost.com/my-favorite-apple-products-from-the-last-50-years.html
1:01:00 LN: How I Use AI at Ask Leo! – https://askleo.com/168449
Transcript
teh265
Video
https://youtu.be/st_L87IbgWc
March 18, 20261 hr 3 min
TEH 264: Hacked Traffic Signals. Pokémon Go makes Pizza Bots. AI generated confusion.
In This Episode: Hacked Traffic Signals. Pokémon Go makes Pizza Bots. AI generated confusion.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 GR: Another hacked traffic signal
They have passwords!
https://denverite.com/2026/03/16/denver-crosswalks-hacked-anti-trump-message-explained/
7:00 LN: Confusing parking lots
12:00 Public transportation
16:00 GR: Pizza robots – mined from Pokemongo
https://www.popsci.com/technology/pokemon-go-delivery-robots-crowdsourcing/
19:00 Limits of Google maps
21:00 LN: Benjamin Netanyahu is struggling to prove he’s not an AI clone – the future of AI
This is currently the worst AI we’ll see; it’s only getting better and more difficult to detect.
Even without AI being used, accusations of AI are an issue.
What happens when we can believe … nothing?
29:00 GR: https://www.404media.co/ai-job-loss-research-ignores-how-ai-is-utterly-destroying-the-internet/
Flawed because the inputs must be guessed
AI slop: does it hurt jobs?
Will it hurt spammers and junk news?
32:00 LN: “Slop” – prejorative thrown about for both good/useful and bad/misleading AI usage
Seems to be repeating same fears we’ve had for a while, before AI
Bots answering questions instead of websites
38:00 GR: Is a job that didn’t exist 20 years ago really “lost” if AI replaces it?
LN: Were buggy whip manufacturers’ jobs “lost”? And if so, was there a responsibility to somehow preserve them?
Get Off My Lawn!
46:00 LN: But whatabout… !!!
Occasionally: an honest question about something more
More commonly: an attempt to one-up / bring down the original premise/content/whatnot
48:00 GR: If only they would add…
Ain’t It Cool!
55:00 LN: Young Sherlock (Amazon Prime), https://www.imdb.com/title/tt8599532/
56:00 GR: Fackham Hall, https://www.imdb.com/title/tt29008225/
BSP: Blatant Self-Promotion
59:00 LN: Why Password Managers Are [Still] Safer than the Alternatives – https://askleo.com/5555
1:00:00 GR: https://macmost.com/macbook-neo-full-review.html
Transcript
teh264
Video
https://youtu.be/YIfe8MZXC4k
 
March 11, 20261 hr 7 min
TEH 263: Apple’s Cheapest MacBook Ever. When AI makes friends with AI. Tech Bubble Insights.
In This Episode: Apple’s Cheapest MacBook Ever. When AI makes friends with AI. Tech Bubble Insights.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
1:00 GR: MacBook Neo
I wasn’t right, but that’s OK
Why this is more interesting than I thought
The tablet-replaces-the-PC future is now dead
Low power opens possibilities
19:31 LN: What is the point behind moltbook?
Meta to Acquire AI-Only Social Media Platform Moltbook https://www.wsj.com/tech/ai/meta-to-acquire-ai-only-social-media-platform-moltbook-0d9cd9d6
https://www.moltbook.com/
29:00 Why does Meta want this?
30:20 GR: AI Psychosis
https://www.404media.co/ai-psychosis-help-gemini-chatgpt-claude-chatbot-delusions/?ref=daily-stories-newsletter
32:50 People think the AI is talking to them
50:00 LN: The car wash test
Gemini: meh
Claude: fail
OpenAI GPT 5: fail
57:00 GR: Holding AI in check
59:00 LN: Frustrating surveys
Ain’t it Cool
1:00:00 LN: The AI Fix podcast – 5 ways the AI bubble could burst
VC with some very interesting perspectives on AI
Random for flavor of the discussion:
The number of hours worked by the average knowledge worker has only increased due to technology.
We use AI. Across every part of the business at my new firm.
I think there’s the potential that if we end up getting more efficient models, which everyone wants, that actually makes all of the infrastructure spend that has happened Less.
1:03:00 GR: Anaconda (movie 2025)
The Bridgerton X Naked Gun spoof that Leo was talking about is “Farkham Hall”.
BSP: Blatant Self-Promotion
1:05:00 LN: How Do I Gain Administrative Access to a Secondhand Computer? – https://askleo.com/12356
1:06:00 GR: 15 Ways the MacBook Neo Is Different From Other MacBooks
Transcript
263
Video
https://youtu.be/_ekuvBlQXTs
March 4, 20261 hr 1 min
TEH 262: Apple announcements. Coding with AI. Copyright and AI.
In This Episode: Apple announcements. Coding with AI. Copyright and AI.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 GR: New Apple Stuff
Might be a new low-end Macbook.
8:00 Lightweight?
13:00 GR: Vibe Coding Limits
Coding with AI
20:00 LN: Learning how to ask for what you want
Different possibilities for the future
30:00 GR & LN: Let’s talk about why we use AI art again in light of https://www.theverge.com/policy/887678/supreme-court-ai-art-copyright
38:00 Faking real
40:00 How will it apply to video?
How about using AI as a CGI tool?
46:00 LN: Server moves. Very geeky, but kinda interesting maybe.
And how I took 50 sites offline with a single click. Oops.
Ain’t it Cool
55:00 LN: The Collected Stories of Arthur C. Clarke – (Audio)
56:00 GR: Rental Family (Disney+)
BSP: Blatant Self-Promotion
58:00 LN: How Does Cloud Storage Work? – https://askleo.com/75658
59:00 GR: 10 Ways To Start Recording Video With Your iPhone Fast
https://macmost.com/10-ways-to-start-recording-video-with-your-iphone-fast.html
Transcript
teh_262
Video
https://youtu.be/E5OqViJQREk
February 25, 20261 hr 15 min
TEH 261: Solving Server Headaches With AI, Age Verification Dilemmas, and the Software Subscription fight.
In This Episode: Solving Server Headaches With AI, Age Verification Dilemmas, and the Software Subscription fight.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
LN: More Claude tricks
1:00 Slow server log analysis
11:00 Ask Leo! Question repository analysis
19:00 Journal recovery
https://leo.notenboom.org/my-writing-journey/
21:00 LN: Age verification & Discord?
https://www.techradar.com/computing/software/what-a-great-way-to-kill-your-community-discord-users-are-furious-about-its-new-age-verification-checks-and-are-now-hunting-for-alternatives
24:00 GR: Protecting children vs protecting privacy: https://9to5mac.com/2026/02/24/reddit-and-discord-are-both-in-trouble-over-controversial-age-verification-service/
To protect kids: age verification
But then that violates privacy as you have to confirm your ID
Another aspect: blocking kids from social media makes it harder for them to have a political voice (organize for protests, etc)
30:00 Some call for Google and Apple to take this over
34:00 Maybe we need some sort of special org? But even then how would they do both?
49:00 GR: Software subscriptions (again)
You don’t “own” your software
Software needs updating, it isn’t a consumable or physical product
1:06:00 Gary’s journal is transcribed while we talk!
Ain’t it Cool
1:09:00 GR: Knight Of the Seven Kingdoms
1:10:00 LN: same
BSP: Blatant Self-Promotion
1:11:00 GR: Using Text Files As a Productivity Tool
1:12:00 LN: The Nirvana Fallacy https://askleo.com/179344
Transcript
teh_261
Video
https://youtu.be/rqqqs9D96ZY
February 11, 20261 hr 3 min
TEH 260: The Internet Archive saves an old car. AI Bird IDs. Claude code. Ringing Lost Dogs.
In This Episode: The Internet Archive saves an old car. AI Bird IDs. Claude code. Ringing Lost Dogs.
This week the TEH Podcast is hosted by Leo Notenboom, the “Chief Question Answerer” at Ask Leo!, and Gary Rosenzweig, the host and producer of MacMost, and mobile game developer at Clever Media.
(You’ll find longer Bios on the Hosts page.)
Top Stories
0:00 LN: Internet Archive to the rescue
My wife is visiting my sister-in-law, and the parking brake in her 2000 Honda CRV (originally my mother’s car) froze up. The pull-lever i the center wouldn’t budge. I got messaged for help.
I searched for “2000 honda crv maintenance manual”. The second entry is The Internet Archive’s scan of the ~1400 page manual. https://archive.org/details/HondaCRV19972000
I was able to send her images from the manual about how to access and lubricate the pull lever.
This isn’t the first time IA has popped up randomly to help. It’s an amazing resource.
5:45 LN: What bird is that?
Another story of things coming together.
My wife takes a photo with her phone (Pixel 4a) of a hawk sitting on a fence in our neighborhood. https://flic.kr/p/2rVhrLG
The photo is auto-uploaded to her Google Photos account.
I grab a copy and crop it. Original is 4032×3024, so there are lots of opportunities. Not bad. https://flic.kr/p/2rVjh8d
7:00 I fire up Topaz Gigapixel AI, and, with a little adjustment of settings, upscale the image 4x. I then crop it further to focus more closely on the bird. Also not bad, though there are some tell-tale signs that this was AI upscaled. https://flic.kr/p/2rVisjk
9:15 My wife asks me what kind of hawk that might be. No clue. So I decided to try … ChatGPT. I upload the upscaled image, and ask simply, “What kind of bird is this?”
Likely ID: Red-tailed Hawk (juvenile)
Based on the bulky buteo shape, overall brown upperparts, the pale “checkerboard” pattern on the wings, and the strongly banded tail (common in young birds before they develop the classic red tail), this looks most consistent with a juvenile Red-tailed Hawk.
We do indeed have red-tailed hawks around here. It’s interesting that it ID’d a juvenile.
15:00 Identify birds.
https://merlin.allaboutbirds.org/
18:00 LN: Claude Code
Installed on my PC because it promised to be able to work on local data
20:00 Non-trivial install (at least for Windows – WSL, and then you’re running in an Ubuntu bash shell).
21:10 Scenario 1: My Obsidian vault – all plain text (.md) files. I can now ask questions and run analyses across the entire collection of notes.
24:00 Scenario 2a: My personal blog. Pointed it at leo.notenboom.org – did OK, but incomplete.
25:00 Scenario 2b: exported by personal blog content from WordPress as an XML file. Dense, lots of cruft. Gave that to Claude and got a very complete, detailed analysis / summary of what I’ve been doing there since 2004.
27:00 Scenario 3: downloaded the contents of 23 years of Ask Leo! Articles.
https://askleo.com/ask-leo-analysis-via-claude-code/
38:00 GR: Ring Doorbell Superbowl Ad ?
Pretty sure I was “ringing this bell” many years ago right here
LN: We Rate Dogs take on it: https://www.tiktok.com/@weratedogs/video/7605333665031245069
Ain’t it Cool
GR: Dungeon Crawler Carl
LN: Archive.org
BSP: Blatant Self-Promotion
LN: Managing Windows File Explorer’s Navigation Pane – https://askleo.com/188995
GR: How To Keep Using Pages, Numbers and Keynote If You Don’t Want Apple Creator Studio
Transcript
teh_260
Video
https://youtu.be/Q7JXOLNvLi4
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