Sometimes life’s detours teach us unexpected lessons. Adam Engst shares how a cycling accident and a broken bone in his wrist forced him to rely on iOS 27’s improved dictation and macOS Voice Control—and how he discovered both their impressive capabilities and frustrating limitations. While convalescing, he found time to document the quirks of setting up a new iPhone 18 Pro and Apple Watch Series 12, including eSIM transfers, Google Account chaos, and Apple Pay verification headaches. For those exploring Apple’s AI assistant, Adam highlights David Pogue’s extensive testing of Siri AI with 125 real-world prompts and invites readers to crowdsource their own hits and misses. Glenn Fleishman rounds out the issue by explaining iPhone Handoff, the new iOS 27 feature that lets you share an eSIM between two iPhones—useful for a few, seemingly irrelevant for most. Notable Mac app releases this week include Carbon Copy Cloner 7.2, ChronoSync 12.0.3, Evernote 11.34.8, Fantastical 4.2 and Cardhop 2.5, OmniFocus 4.9, OmniOutliner 6.3, and PowerPhotos 3.4.7.
David Pogue’s comprehensive testing of 125 Siri AI requests reveals what Apple’s revamped assistant can handle and where it still falls short. Share your own experiences in the comments.
iOS 27 finally adds a few text-editing commands to dictation—something Adam Engst suggested six years ago. A broken bone in his wrist gave him the chance to test these improvements extensively, along with macOS Voice Control’s capabilities and quirks.
Adam Engst shares his experience setting up a new iPhone 18 Pro and Apple Watch Series 12, including the best restoration method, Google account chaos, Apple Pay verification hassles, and a surprise Apple One offer.
Apple has added an option in iOS 27 that lets you share one eSIM with two iPhones, allowing each to function—one at a time—as your incoming phone line, destination for messages, and Find My location. Who needs this?
Watchlist
Brings scheduling setting updates to the drive cloning and backup utility. ($49.99 new, free update, 30.1 MB, macOS 13+)
Enhances the cloud-managed folder readiness check. ($49.99 new, free update, 102.7 MB, macOS 10.14+)
Brings an enhanced PDF editor to the information management app. (Free/$99/$249 new, free update, 348.2 MB, macOS 11+)
Adds support for Siri AI to work with Fantastical calendars. ($56.99 annual subscription, free update, various sizes, macOS 12+)
Adds compatibility with macOS 27 Golden Gate and support for date-parsing assistance via Apple Intelligence. ($74.99 new, free update, 41.4 MB, macOS 15.2+)
Outlining and information organization apps add compatibility with macOS 27 Golden Gate. ($24.99/$99.99 new, free update, 59.1 MB, macOS 15+)
Adds support for star ratings in AppleScript and Shortcuts in macOS 27 Golden Gate. ($39.95 new, free update, 41.4 MB, macOS 14+)
