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Is Apple’s AI Predicament Fixable?→

On Sunday, Bloomberg’s Mark Gurman published a comprehensive recap of Apple’s AI troubles. There wasn’t much new in Gurman’s story, except quotes from unnamed sources that added to the sense of conflict playing out inside the company. That said, it’s perfect if you haven’t been paying close attention since Apple Intelligence was first announced last June.

What’s troubling about Apple’s predicament isn’t that Apple’s super mom and other AI illustrations looks like they were generated in 2022, a lifetime ago in the world of AI. The trouble is what the company’s struggles mean for next-generation interactions with devices and productivity apps. The promise of natural language requests made to Siri that combine personal context with App Intents is exciting, but it’s mired in multiple layers of technical issues that need to be solved starting, as Gurman reported, with Siri.

The mess is so profound that it raises the question of whether Apple has the institutional capabilities to fix it. As M.G. Siegler wrote yesterday on Spyglass:

Apple, as an organization, simply doesn’t seem built correctly to operate in the age of AI. This technology, even more so than the web, moves insanely fast and is all about iteration. Apple likes to move slowly, measuring a million times and cutting once. Shipping polished jewels. That’s just not going to cut it with AI.

Having studied the fierce competition among AI companies for months, I agree with Siegler. This isn’t like hardware where Apple has successfully entered a category late and dominated it. Hardware plays to Apple’s design and supply chain strengths. In contrast, the rapid iteration of AI models and apps is the antithesis of Apple’s annual OS cycle. It’s a fundamentally different approach driven by intense competition and fueled by billions of dollars of cash.

I tend to agree with Siegler that given where things stand, Apple should replace a lot of Siri’s capabilities with a third-party chatbot and in the longer-term make an acquisition to shake up how it approaches AI. However, I also think the chances of either of those things happening are unlikely given Apple’s historical focus on internally developed solutions.

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Inside Airbnb’s App Redesign: An AppStories Interview with Marketing and Design Leads→

Last week, I was in LA for Airbnb’s 2025 Summer Release. As part of the day’s events, Federico and I interviewed Jud Coplan, Airbnb’s Vice President of Product Marketing, and Teo Connor, Airbnb’s Vice President of Design, for AppStories to talk about the new features and app the company launched. It was a great conversation that you can watch on YouTube:

or listen to the episode here:

Last week’s launch was a big one for Airbnb. The company debuted Services and reimagined and expanded Experiences. Services are the sort of things hotels and resorts offer that you used to give up when booking an Airbnb stay. Now, however, you can book a chef, personal trainer, hair stylist, manicurist, photographer, and more. Better yet, you don’t have to book a stay with an Airbnb host to take advantage of services. You can schedule services in your hometown or wherever you happen to be.

Experiences aren’t entirely new to Airbnb, but have been expanded and integrated into the Airbnb app in a way that’s similar to Services. Services allow you to get the most out of a trip from locals who know their cities best, whether that’s a cultural tour, dining experience, outdoor adventure, or something else.

Chef Grace explaining how to serve sadza.

Chef Grace explaining how to serve sadza.

While I was in LA, I prepared a meal alongside several other media folks from around the world. Our instructor was Chef Kuda Grace from Zimbabwe at Flavors from Afar. We made sadza with peanut butter and mustard greens and then sat down together to compare notes from the day’s events, tell stories about our dining experiences, and get to know each other better.

The evening was a lot of fun, but what struck me most about it was something we touched upon in this week’s episode of AppStories. The goal of Airbnb’s redesigned app is to get you to leave it and go out into the world to try new things. It reduces the friction and anxiety of taking the plunge into something new and emphasizes social interactions in the real world instead of on a screen. In 2025, that’s unusual for an app from a big company, and it was fascinating to talk to Teo and Jud about how they and their teams set out to accomplish that goal.

I like Airbnb’s redesigned app a lot. It’s playful, welcoming and easy to use. What remains to be seen is whether Airbnb can pull off what it’s set out to accomplish. It isn’t the first company to try to pair customers with local services and experiences. Nor is it Airbnb’s first attempt at experiences. However, the app is a solid foundation, and if my experience at dinner in LA was any indication, I suspect Airbnb may be onto something with Services and Experiences.

Disclosure: The trip to LA to conduct my half of this interview was paid for by Airbnb.

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Federico’s Latest Automation Academy Lesson: Building a Better Web Clipper with Shortcuts and AI→

A webpage saved with Universal Clipper.

A webpage saved with Universal Clipper.

I share Federico’s frustration over saving links. Every link may be a URL, but their endpoints can be wildly different. If like us, you save links to articles, videos, product information, and more, it’s hard to find a tool that handles every kind of link equally well.

That was the problem Federico set out to solve with Universal Clipper, an advanced shortcut that automatically detects the kind of link that’s passed to it, and saves it to a text file, which he accesses in Obsidian, although any text editor will work.

Universal Clipper integrates with the Obsidian plugin Dataview, too.

Universal Clipper integrates with the Obsidian plugin Dataview, too.

Universal Clipper, which Federico released yesterday as part of his Automation Academy series for Club MacStories Plus and Premier members, is one of his most ambitious shortcuts that draws on multiple third-party apps, services, and command line tools in an automation that works as a standalone shortcut or as a function that can send its results to another shortcut. As Federico explains:

I learned a lot in the process. As I’ve documented on MacStories and the Club lately, I’ve played around with various templates for Dataview queries in Obsidian; I’ve learnedhow to take advantage of the Mac’s Terminal and various CLI utilities to transcribe long YouTube videos and analyze them with Gemini 2.5; I’ve explored new ways to interact with web APIs in Shortcuts; and, most recently, I learned how to properly prompt GPT 4.1 with precise instructions. All of these techniques are coming together in Universal Clipper, my latest, Mac-only shortcut that combines macOS tools, Markdown, web APIs, and AI to clip any kind of webpage from any web browser and save it as a searchable Markdown document in Obsidian.

Although the shortcut may be complex, the best part of Federico’s post is how easy it is to follow. Along the way, you’ll learn a bunch of techniques and approaches to Shortcuts automation that you can adapt for your own shortcuts, too.

Automation Academy is just one of many perks that Club MacStories Plus and Club Premier members enjoy including:

  • Weekly and monthly newsletters 
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  • A vibrant Discord community of smart app and automation fans who trade a wealth of tips and discoveries every day
  • Live Discord audio events after Apple events and at other times of the year

On top of that, Club Premier members get AppStories+, an extended, ad-free version of our flagship podcast that we deliver early every week in high-bitrate audio.

Use the buttons below to learn more and sign up for Club MacStories+ or Club Premier.

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Amazon Adds Links to Purchase Books to Its Kindle App→

As reported by Andrew Liszewski at The Verge, Amazon has updated the Kindle app to add a “Get Book” button, a direct result of last week’s contempt order entered by Judge Gonzalez Rodgers. When tapped, it takes users to the Amazon page for the book in Safari with the Kindle version selected. Before today’s update, you couldn’t purchase a book without going to Safari first.

In a low key statement to The Verge over email, Amazon’s Tim Gillman said:

We regularly make improvements to our apps to help ensure we are providing customers the most convenient experience possible. By selecting ‘Get Book’ within the Kindle for iOS app, customers can now complete their purchase through their mobile web browser.

I expect other companies will follow Amazon and Spotify’s leads in the coming weeks. Although Apple has appealed Judge Gonzalez Rodgers’ contempt order, the Judge declined to stay its enforcement during the appeals process. It’s always possible an appeal could force Amazon and others to undo changes like this, but I think a more likely outcome is that an appellate court allows Apple to charge a fee where Judge Gonzalez Rodgers wasn’t – one that’s lower than the 27% that got Apple into trouble in the first place.

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Post-Chat UI→

Fascinating analysis by Allen Pike on how, beyond traditional chatbot interactions, the technology behind LLMs can be used in other types of user interfaces and interactions:

While chat is powerful, for most products chatting with the underlying LLM should be more of a debug interface – a fallback mode – and not the primary UX.

So, how is AI making our software more useful, if not via chat? Let’s do a tour.

There are plenty of useful, practical examples in the story showing how natural language understanding and processing can be embedded in different features of modern apps. My favorite example is search, as Pike writes:

Another UI convention being reinvented is the search field.

It used to be that finding your flight details in your email required typing something exact, like “air canada confirmation”, and hoping that’s actually the phrasing in the email you’re thinking of.

Now, you should be able to type “what are the flight details for the offsite?” and find what you want.

Having used Shortwave and its AI-powered search for the past few months, I couldn’t agree more. The moment you get used to searching without exact queries or specific operators, there’s no going back.

Experience this once, and products with an old-school text-match search field feel broken. You should be able to just find “tax receipts from registered charities” in your email app, “the file where the login UI is defined” in your IDE, and “my upcoming vacations” in your calendar.

Interestingly, Pike mentions Command-K bars as another interface pattern that can benefit from LLM-infused interactions. I knew that sounded familiar – I covered the topic in mid-November 2022, and I still think it’s a shame that Apple hasn’t natively implemented these anywhere in their apps, especially now that commands can be fuzzier (just consider what Raycast is doing). Funnily enough, that post was published just two weeks before the public debut of ChatGPT on November 30, 2022. That feels like forever ago now.

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Sundar Pichai Testifies That He Hopes Gemini Will Be Integrated into iPhones This Fall→

Ever since Apple announced its deal to integrate ChatGPT into Siri, there have been hints that the company wanted to make deals with other AI providers, too. Alphabet CEO Sundar Pichai has added fuel to the rumors with testimony given today in the remedy phase of the search antitrust case brought against it by the U.S. Department of Justice.

In response to questions by a DOJ prosecutor, Pichai testified that he hoped Google Gemini would be added to iPhones this year. According to a Bloomberg story co-authored by Mark Gurman, Davey Alba, and Leah Nylen:

Pichai said he held a series of conversations with Apple Chief Executive Officer Tim Cook across 2024 and he hopes to have a deal done by the middle of this year.

This news isn’t surprising, but it is welcome. Despite Google’s early stumbles with Bard, its successor, Gemini, has improved by leaps and bounds in recent months and has the advantage of being integrated with many of Google’s other products that have a huge user base. What will be interesting to see is whether Gemini is integrated as an alternative fallback for Siri requests or whether Apple and Google ink a broader deal that integrates Gemini into other aspects of iOS.

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Sycophancy in GPT-4o→

OpenAI found itself in the middle of another controversy earlier this week, only this time it wasn’t about publishers or regulation, but about its core product – ChatGPT. Specifically, after rolling out an update to the default 4o model with improved personality, users started noticing that ChatGPT was adopting highly sycophantic behavior: it weirdly agreed with users on all kinds of prompts, even about topics that would typically warrant some justified pushback from a digital assistant. (Simon Willison and Ethan Mollick have a good roundup of the examples as well as the change in the system prompt that may have caused this.) OpenAI had to roll back the update and explain what happened on the company’s blog:

We have rolled back last week’s GPT‑4o update in ChatGPT so people are now using an earlier version with more balanced behavior. The update we removed was overly flattering or agreeable—often described as sycophantic.

We are actively testing new fixes to address the issue. We’re revising how we collect and incorporate feedback to heavily weight long-term user satisfaction and we’re introducing more personalization features, giving users greater control over how ChatGPT behaves.

And:

We also believe users should have more control over how ChatGPT behaves and, to the extent that it is safe and feasible, make adjustments if they don’t agree with the default behavior.

Today, users can give the model specific instructions to shape its behavior with features like custom instructions. We’re also building new, easier ways for users to do this. For example, users will be able to give real-time feedback to directly influence their interactions and choose from multiple default personalities.

“Easier ways” for users to adjust ChatGPT’s behavior sound to me like a user-friendly toggle or slider to adjust ChatGPT’s personality (Grok has something similar, albeit unhinged), which I think would be a reasonable addition to the product. I’ve long argued that Siri should come with an adjustable personality similar to CARROT Weather, which lets you tweak whether you want the app to be “evil” or “professional” with a slider. I increasingly feel like that sort of option would make a lot of sense for modern LLMs, too.

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How Does This Keep Happening?→

Today, Blue Prince, a critically acclaimed videogame appeared on Apple’s App Store. The trouble was, it wasn’t offered for sale by its developer, Dogubomb, or its publisher, Raw Fury. The real Blue Prince is only available on the Xbox, PlayStation, and PC.

What appeared on the App Store, and has since been removed, was an opportunistic scam as Jay Peters explained for The Verge:

Before it was removed, I easily found one iOS copy of the game just by searching Blue Prince on the App Store – it was the first search result. The icon looked like it would be the icon for a hypothetical mobile version of the game, the listing had screenshots that looked like they were indeed from Blue Prince, and the description for the game matched the description on Steam.

The port was available long enough for Blue Prince’s developer and publisher to post about it on Bluesky and, according to Peters, for the fake to reach #8 in the App Store Entertainment category. I feel for anyone who bought the game assuming it was legit given Peters’ experience:

I also quickly ran into a major bug: when I tried to walk through one of the doors from the Entrance Hall, I fell through the floor.

This isn’t the first time this sort of thing has happened. As Peters points out it happened to Palworld and Wordle too. Other popular games that have appeared on the App Store as janky scam ports include Cuphead, a version of Balatro that appeared before its official release on iOS, and Unpacking.

This seems like the sort of thing that could be fixed through automation. Scammers want users to find these games, so they can make a quick buck. As a result, the name of the game is often identical to what you’d find on the Steam, Xbox, or PlayStation stores. It strikes me that a combination of automated searching for the top games on each store, combined with an analysis of how quickly a game is moving up the charts would catch a lot of this sort of thing, flagging it for reviewers who could take a closer look.

By the way, if you haven’t tried Blue Prince, you should. It’s an amazing game and early contender for game of the year. You can learn more about the game and find links to where to buy it here. Also, Brendon Bigley, my NPC co-host, has an excellent written and video review of Blue Prince on Wavelengths.

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Contabulation→

Rumors have been flying for a while about a planned redesign for iOS 19. One of the rumors is that iOS tab bars will support search bars, which led Ben McCarthy, the developer of Obscura, to write a terrific breakdown of how tab bars should be used:

If search is the primary form of navigation, as in Safari, Maps, or Callsheet, it should be at the bottom. If a search bar is just used for filtering content already on screen, then it can make more sense to leave it at the top, as scrolling is probably the more natural way to find what you’re looking for (the Settings app is a good example of this). So I’m delighted at the rumours that iOS 19’s Tab Bars can adapt into Search Bars when needed. I think it’ll be [a] big improvement and allow for more flexible navigation patterns with less code.

But Ben didn’t just provide pointers on how tab bars should be used. They also explained that tab bars:

  • should support actions and context menus,
  • accommodate more than five tabs,
  • and allow for user-generated tabs, something that is common on macOS.

It’s a great post, well worth studying as we wait to see whether and how far Apple will go in modifying the tab bar. As Ben notes, the tab bar has been around since the beginning of the iPhone, has changed very little, and is due for a redesign. I agree.

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