This week, Mike and Damashe dig into Earshot build 99, react to WWDC 26, and ask the big question: are AI agent devices actually ready to replace your phone? Spoiler: your ride might end up in the wrong city.

What We Talked About

Earshot Update - Build 99

  • The new alphabetical library picker is live, with a count of how many podcasts are under each letter
  • Per-podcast playback speed is now working: set a default speed, override it for individual shows, and it remembers your preference automatically
  • The database migration bug from builds 88-95 is fixed; if your app was spinning and crashing, update to build 99
  • The app now gives you a useful error message instead of just failing silently if something goes wrong with the database
  • If you are on TestFlight and want to send feedback, email feedback@technicallyworking.show - do not use the TestFlight feedback form, because Mike cannot reply to you there
  • To get on the beta, find Michael on Mastodon

Apple Deals Worth Knowing

  • AirPods Pro 3 spotted at $179 on Amazon, Best Buy, and possibly Walmart
  • AirPods 4 at $99
  • Apple Watch Series 11 (42mm GPS) at $299

WWDC 26 Impressions

  • Mike went in with low expectations and came out a little underwhelmed
  • Damashe has not watched the keynote but has listened to everyone talk about it
  • Apple showed features live and uncut, which seems intentional - they want to prove the demos are real
  • Certain AI features require M3 Pro or better on Mac, M4 or better on iPad, and iPhone 17 Pro
  • iOS 26 and 27 compatibility stays the same - if your device runs 26 it will run 27, you just may not get all the local AI capabilities
  • Damashe called the OS unification direction, and he would like you to use the hashtag DamasheWasRight accordingly

iOS 27 Safari Notify

  • Apple Intelligence can now watch a Safari tab and notify you when something changes
  • Steven Robles used it to get notified when the Unify travel router came back in stock
  • Both Mike and Damashe immediately thought: Ubiquiti restocks

Touchscreen MacBook Speculation

  • Mark Gurman is pointing toward a high-end OLED touchscreen MacBook Pro at a significant price premium
  • Damashe's alternate theory: what if Apple makes a detachable touchscreen MacBook Neo instead of going ultra-premium
  • The Neo already runs macOS on an A18 Pro chip at $600; a touch-capable detachable version aimed at schools and everyday users could make more sense than a $3,200 pro machine
  • Both agree: a MacBook with cellular would be an instant buy, no questions asked

Are AI Agent Devices Ready to Replace Your Phone?

  • OpenAI is rumored to be working on a new form factor device built around voice interaction
  • Damashe's argument: not yet, for several reasons - apps, authentication, companies not wanting to be commoditized, and the lack of strong local compute
  • Uber and Amazon are not going to sit still while an agent turns them into a background API
  • The local vs. cloud routing problem is real: you need a local model to manage where requests go, and we are not there on mobile yet
  • Both see 2029-2030 as a realistic window for local compute on personal devices being good enough for most tasks
  • The Plaud Pin has been sitting on a nightstand for months as evidence

Siri and Third-Party Mail

  • Siri can now surface airline reservations when you call airlines
  • Open question: does it work if your reservation is in Gmail or Outlook instead of Apple Mail

Shortcuts Getting Smarter

  • The new AI-assisted Shortcuts builder could be the most useful thing in iOS 27 if it actually works
  • Federico Viticci's hope: get Sherlocked properly this time

Links and Contact

  • Send feedback: feedback@technicallyworking.show
  • TestFlight beta for Earshot: find Michael on Mastodon at payown@dragonscave.space
  • Damashe on Mastodon: damashe@technically.social
  • Bot: tw@technically.social
  • Support the show: technicallyworking.show, click Support Us

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