Has Apple Finally Figured Out Smarter Siri?
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Dan Morin
Where is Daredevil A minor.
Micah Sargent
Don't miss the return of Marvel Television's Daredevil Born Again. So what's next? I feel liberated. We're gonna take this city back over medicated in an all new season now streaming only on Disney plus. They're hunting us. It's time we started hunting them. I can work with that. This should be tons of fun. Marvel Television's Daredevil Born Again now streaming only Disney. Coming up on iOS today. WWDC is just around the corner. So Dan Moran joins me to talk about what you can expect at the big event. Stay tuned.
Dan Morin
Podcasts you love from people you Trust. This is TWIT.
Micah Sargent
This is iOS Today, episode805 with Dan Morin and me, Micah Sargent. Recorded Tuesday, May 26, 2026 for Thursday, June 4, 2026. WWDC what to Expect. Hello and welcome to iOS Today, the show where we talk all things iOS, iPadOS, WatchOS, HomePod, OS and all the OSs Apple has on offer. I am your host, Micah Sargent. Rosemary Orchard is not with us this week, but I'm joined by the wonderful Dan Morin of Six Colors. Welcome back, Dan.
Dan Morin
Hello, Michael. Always good to be back. Talk about WWDC or as I like to call it, why would dogs cheat? You need a mnemonic is what I'm saying. You need something to remember.
Micah Sargent
I like, why would they?
Dan Morin
Why would they? I mean, I mean, unless they're playing poker. I mean, you know, oh, you know,
Micah Sargent
one of those dogs.
Dan Morin
One of those. At least one, maybe all of them.
Micah Sargent
Now I'm trying to think about what dog breed do I feel is most likely.
Dan Morin
I feel that I've taken you off track now and I said dog to Maika and now, now Micah's brain is
Micah Sargent
off and running dog is my squirrel. Think about that for a second. Anyway, let's get into it. This is the episode where we're going to talk about what we think we can expect at WWDC this year. Of course, Apple's worldwide Developer conference. Developers all around the world, believe it or not, join to watch Apple announce what's next for its various platforms. That means new features in iOS, new features in iPados, new features in WatchOS, occasionally some new hardware. But the big thing here is it seems an ongoing narrative that this is a quote unquote snow leopard update. Can you tell me, can you tell us what that means?
Dan Morin
Cast your mind back, Micah, to a time many, many years ago. The year was 2009.
Micah Sargent
Can you believe it?
Dan Morin
I'm crumbling into dust as I look that year up, Snow Leopard came on the heels of Mac OS X Leopard, appropriately enough. And the idea behind it was kind of billed as no new features. We're just going to fix everything that's broken. We're going to make little tweaks and maintenance updates. All those problems you've had with macOS, we're going to make sure they work great. Now, the no new features thing was of course, a bit marketing speak because there certainly were some new features, but it lacked some of the marquee features, I think, because a lot of it was focused on under the hood improvements. And you will hear lots of people laud it as one of the last best releases of macOS because they didn't just cram new features in, they went and actually fixed stuff. So people feel very positively in many cases about Snow Leopard. That said, you know, is that what we're expecting this year? It's unclear. I think there's a lot of talk obviously about this idea that they will fix a lot of problems in iOS 27 and that would be great if they did. I know we all certainly have our problems with various Apple platforms that we'd like to see get repaired, our little pet peeves and bugbears. But yeah, I expect there to still be some new features despite all of that, much as there were with Snow Leopard.
Micah Sargent
Yeah. So with this, Siri is kind of the big, one of the big tent pole features. Right. We are supposed to be finally, finally, finally getting this smarter Siri. Now, we saw the company advertise a Siri that had more personal context, that had more understanding of what it was seeing on screen, that was able to interact with your, like your mail app and do more. But none of that has presented itself up to this point. The rumor is that it's something we should be seeing. What, what is this sort of personal context aspect of Siri that we've been promised for so long, but it has yet to be delivered?
Dan Morin
Cast your mind back once again. The year was 2024, the first of many attempts by Apple to say, no, no, no, no, no, we've got this AI thing figured out, we know what we're going to do. And they announced a bunch of features. Among them, as you said, Siri with personal idea behind personal context was Siri could look at an index on your device of all the things it knew about you from your mail and your calendar and all the, like, you know, personal information that it could garner and securely on your device. It would then be able to use that information to help provide intelligent answers to you. So the classic example being as Apple themselves showed off, what time does my mom's flight arrive at the airport? And for this it needs to know, well, who's your mom? First of all, can I look through your emails and your text messages and basically divine a relationship or have you somewhere maybe specified that say in context where do I know about their flight? I can go through and look again at your email and your messages and see or your calendar, do you have something in there? Can I look up that flight information if necessary?
Micah Sargent
Right.
Dan Morin
There's a bunch of steps in there and the idea being you ask a complex query, it gives you a simple answer. That feature which was I'm not going to say demoed but I'm going to say shown in Apple's pre produced WWC 2024 video was never demoed as far as I know to anybody outside of the company, including myself. I was in briefings that year. I never saw it and in is widely considered to basically never have worked. But that didn't stop them from advertising that very feature in ads that ran on network television talking about how great this was going to be, which has gotten them in trouble, including with a class action lawsuit. Now last year you may cast your mind back once again. 2025, you know, during its WWC it didn't spend time on these features necessarily, but in conversations did say essentially those features are still coming and will arrive in the next year. A very vague phrasing that could have meant basically anything. They are now running out of time to deliver on their promise which is why essentially everybody expects that they will talk about it this year. The question is how much weight will they give it? Having spent two years basically showing off something that didn't exist and then not being able to deliver it. And remember this year meant to them the calendar year of 2026, which means even if they talk about them in June, those features could arrive basically anytime before December 31st. So yeah, we'll see exactly how much of that gets delivered. But obvious obviously in the meantime AI has continued to be a growing concern in the tech industry and something that a lot of people consider Apple to have kind of missed the boat on. And Apple's going to be working hard to correct that. What it considers misapprehension with its announcements this year.
Micah Sargent
Yeah, I mean this has been the thing that I've wanted for the longest. You know, having it announced and thinking about what it could be at, being hopeful about it despite Siri sort of letting me down in the past. Funny, I. Siri.
Dan Morin
Not Siri.
Micah Sargent
Siri. Ah, very good, very good.
Dan Morin
Thank you, thank you. Now I've triggered every single thing in my room right now.
Micah Sargent
It's great.
Dan Morin
Nailed it.
Micah Sargent
Because the, the thing that we haven't yet seen nailed by the third parties that are doing these LLM based systems is that deep integration that a first party could offer. And by that I mean I should on the Apple side of things. So on Mac os I can download Gemini, I can download Claude, I can download the one from OpenAI and can you tell that's I don't use that one anymore and I can sort of through the use of special accessibility permissions and other automation permissions, get it to do some stuff. But it doesn't. It also means that I have to log into those services with, you know, oauth into those services with all of my. I don't.
Dan Morin
And you have to give those services access to your data and comfortable with them having that. And this was a big part of Apple's argument with this feature is we will do it on device so it's secure and if we need to go out to off device, we have this private cloud compute model. They spent a lot of time talking about that back in 2024, that essentially we have worked really hard to create a cloud system that is secure and private and that we can hand it to your data too. Your data will not be shared outside of that and you will get the results back. And that was purely their attempt to sort of stave off the idea like, well, your device is only so powerful. But if we can throw it to a bunch of computers in the cloud, obviously we can throw way more resources at it. Which was always going to be a challenge with the iPhone because as good as it is, you don't want it sitting there chewing through all this data because it will wear out your battery, it will make your phone really hot, all this stuff.
Micah Sargent
Yeah, yeah. Let's take a quick break from the episode because I want to tell you about NetSuite bringing you this episode of iOS today. Every business asking the same question. How do we make AI work? For us, the possibilities are endless and guessing is too risky. But sitting on the sidelines is not an option because one thing is almost certain, your competitors, yeah, they're already making their move. So no more waiting. With Netsuite by Oracle, you can put AI to work. Today, NetSuite is the number one AI cloud ERP trusted by more than 43,000 businesses. It's a unified suite that brings your financials, inventory, commerce, HR and CRM into a single source of truth. That connected data is what makes your AI smarter. So it doesn't just guess, it knows it intelligently automates routine tasks, delivers actionable insights, helps you cut costs and make fast AI powered decisions with confidence. Plus, you've got total flexibility. From software and IT services to healthcare equipment, manufacturing, financial services and many other great American industries, NetSuite delivers a customized solution for your business. This isn't another bolted on tool, it's AI built into the system that runs your business. Whether your company earns millions or even hundreds of millions, NetSuite helps you stay ahead of the pack. If your revenues are at least in the seven figures. Get NetSuite's free business guide demystifying AI at netsuite.com iOS the guide is free to you at netsuite.com iros netsuite.com iOS thank you NetSuite, for sponsoring this week's episode of iOS today. Head back to the show with this on screen awareness. We've kind of seen a little bit of the on screen awareness, right? I can take a screenshot and it can interact with that, but the Smack Rumors guide describes it says, well let Siri see what's on your screen and complete actions involving whatever you're looking at. If someone texts you an address, you can tell Siri to add it to their contact card. If you're looking at a photo and want to want to send it to someone, you can ask Siri to do it for you. I mean I can already if I'm
Dan Morin
looking at a sort of, sort of do that, but not, I think there's some places where it kind of works. I think what this is supposed to be, you know, we, we actually you and I talked about this last week. Was it with the accessibility features that Apple showed and one of the things being being able to ask questions about say something in the Magnifier app. I think this is kind of an outgrowth of that, which is this idea that whatever is on your screen, it can essentially use some combination of visual intelligence and you know, the ability to do live text, write, read text from your screen and turn that into something potentially actionable. But it sort of goes hand in hand too with the third part of this, which is these, I can't remember now what they called it, but essentially the ability to take actions, right? Like the ability for you to tell Siri to do something and for it to go to whatever app you're talking to and do the thing, whether it's mail or messages, you know, an Apple first party app or a third party app that uses this system called App Intents. And so that is sort of the third part of that equation which was the personal context, the on screen awareness and then the ability to go off and run, you know, do things in other apps which is I think kind of similar to what we think of as this agentic AI. You know, I've got a task for you, go do it. You can use the apps that are on my system and then come back when you've done it. None of those things having shipped but those are all things that they still in theory saying will arrive this year.
Micah Sargent
I really think, let me ask you, do you think that given the first party access that that Apple will have to mail messages, your Apple tv, your home accessories, etc is that, is all of that enough? Do you feel right now to make it compelling enough for people to want to shift their behavior if they are currently using the Chat GPT app or the Claude app or something else for doing a lot of their sort of queries and happenings? Do we think that it's going to. You're. It'll be kind of an aha moment. And the reason I also ask this is I just watched Google I O and you know the, the event previous to that where Google showed off some of the other features that it could offer an Android user given all the access that Google would have to that it's to going kind of amazing. And it is exactly the sort of convenience factors that I would be looking for. Having knowledge of my email and being able to say oh right, you're talking to this person now that you need to tell about this change in plans or whatever. So here's what you need to do that I like that idea. Is it enough do we think has Apple in the past perhaps handled the necessary marketing since the company kind of comes to ideas perhaps a little bit later than others and tries to iterate on them in a way that's better than what's already there.
Dan Morin
So. Well, okay, the boring answer first. It depends how well it works. Yeah, right. I mean in the end of the day if it doesn't work well then nobody will use it because and we see this with the way the state of Siri right now, right. Like people trust it with certain tasks but generally kind of low stakes things. Setting timers, playing music, occasionally sending a text message. Right. Most people are not using it. They're certainly not trying to do complex queries and I think that's the first sort of hump for them to overcome is training people that it is more capable now than it used to be and encouraging them to try those things. After years of situations where they shy away from that because it isn't. Now they have the benefit here of, you know, ChatGPT and, and Claude and, and other sort of agents have sort of softened people up to expect these kinds of interactions more. And if you're saying, well, now Siri can do those things too, then perhaps there is a more compelling argument to it. I think at the end of the day, there is something to be said about the fact that your phone particularly contains so much more information about you, that it is so much more hardwired into your life than even your computer these days. Right. Like to have a platform that goes with you everywhere. That is the thing that most people use to do everything from banking to messaging to, you know, checking their stocks. I don't know, like all this stuff, it's in one place and it's a thing that goes with you. It's intensely personal and so saying, well, we can deploy a, an artificial intelligence agent on that platform which already knows all these things about you and then leverage. That seems to make a lot of sense on the face of it. The problem has always been the implementation. And so we are left wondering, do they have, you know, do they have the skills to pull this off? And we've already seen some questions around that because they've done things like gone to Google and said, can we use your models? Which, you know, certainly doesn't engender a lot of faith that the models and the stuff they've been developing in house is up to the task. So I find myself being extremely, I don't want to say cynical, but let's say wary of any announcement that Apple might make because so far their track record hasn't been great when it comes to these things actually working. It's a laudable goal for them to shoot for, especially because privacy is the thing that they've kind of made a lot of their bones about like over the past several years. This idea that unlike a lot of the other platforms, you don't need to worry about your personal data being monetized or compromised. You know, they will keep that secure and you can use your phone without worrying about who is snooping on you. Some people have posted that as kind of being at odds with the idea of AI, which is obviously incredibly data hungry and wants every piece of information you can feed it. Is this a fundamental tension that we're going to see with the fact that Apple needs to balance those two things. I don't know. I honestly don't. I mean I feel like it should be possible. And Apple has talked about how much they've tried to work to make those two things work in harmony, but we don't yet know whether that's something that is feasible or whether they're going to have to make compromises in one direction or the other and which they will choose.
Micah Sargent
Yeah, that was a great answer. And frankly, yeah, we gotta, we gotta wait and see and I gotta wait and see. And sometimes I hate waiting. There are also some other features that I. We've heard that there may be a sort of built in Grammarly. I personally haven't used I. The writing tools never really use those. I don't want them. And so it will be interesting to see
Dan Morin
how
Micah Sargent
the AI grammar writing stuff is going to be integrated across the phone and where I'll be able to turn it off and how quickly I'll be able to turn it off. But I mean, here's the thing, as much as I say that there are people who do benefit from those style of tools and that's fine. Good, good. And glad for you. I just. The thought of screen real estate being taken up by it is a little worrisome and I'm hopeful that. Because I think about sort of the. The suggested words, right. That appear above when you're typing.
Dan Morin
Right.
Micah Sargent
And what if that changes from what it is now to something that is more sort of AI, modern AI driven. And that is concerning. But I'm, you know, I'm inventing something before it's even happened. So it may be okay. It may be just fine. The photos app rumored to be getting features like Extend, which would let you sort of crop out a photo and have more of that enhance, which is just a more AI AI forward way of doing the auto image adjustments and then reframe, which is specifically for spatial photos, letting you change the perspective of an image. I'm reading though that Apple has had some issues getting these working perfectly so we may not see them right away. But I wouldn't be surprised if part of that is the on device nature of it because I can do an extend in Photoshop very easily and very rarely do I have to make too many adjustments to it after the fact. Extend is one of those features that I use with some regularity because often there will be a photo that I'd love to have as a wallpaper on my phone, but the way that it was shot there's not enough room at the top to get it how I want it. And so I just go in Photoshop and then it just puts some more, you know, trees in the background essentially and that's fine. It doesn't bother me because my part of the photo is still there that I, that I want to see. Any of the photo sort of camera stuff seem interesting to you? I know the camera app is supposed to become more customizable in, in the next version of iOS. That kind of scares me a little
Dan Morin
bit because yeah, I mean they did a big redesign last year. I don't know how much more they are going to tweak it there. But obviously the camera app is one of the most prominently used apps, probably the most prominent used app on the iPhone. So it's always a bold move whenever they start changing things there. I think those Apple intelligence related tools, it will be a shame if they can't pull them off in some ways because they kind of feel like table stakes at this point. I mean, there's, like you said, there's tons of other, you know, software that kind of does this stuff and if they can't build it in, what does that really say? So I'm a little suspect of that, you know, of the things they've talked about. I'm very intrigued with this rumor that they're going to use shortcuts is going to add this natural language support potentially where you can have it describe a shortcut to it and it will build it. As somebody who spends a lot of time with shortcuts and knows all too well the shortcomings of shortcuts, I am curious to see whether this is able to avoid any of that by knowing basically what it's doing better than what I'm doing. But I'm not sure that it can overcome some of the problems that are just fundamental to shortcuts as a system. Doesn't matter how well you build the shortcut, some things don't work. So that to me is kind of like a. Will they address those issues as well or will they just be concerned with how well does it build the shortcut? We don't care if the shortcut works at the end.
Micah Sargent
There are supposed to be some design changes as well, making things a little bit more in line with what Liquid Glass has, has provided. There are supposed to be a few new kind of animations that we'll see, but outside of that there's a few little kind of grab bag features. The wallet app is supposed to include a new Create a pass feature so that it can Sherlock. All of the third party pass generating apps. If you've got like a gem, a gym membership or you know, ticket to a local, I don't know, farmers market event. Sure. And you need. It doesn't have an Apple wallet thing. You can basically get the barcode or whatever and turn it into a pass. The weather app has some rumored updates and also supposed to be seeing some new satellite features. I think this is interesting. Apple maps via satellite, photos and messages via satellite, and then other functionality for third party apps like using the satellite API framework and connectivity without needing to be within view of the sky. So in theory, inside somewhere or I guess if it's a cloudy day, I don't know. Yeah, we'll see how all that shakes out. Anything that I didn't mention that you are waiting to hear, you know, from Apple?
Dan Morin
Well, you know, I think, look, it's going to be the year of AI again. I mean, you know, we talked about Siri, obviously. I think this idea that there is going to be a standalone chatbot app for Siri is an interesting one. Will that encourage people to try it out again who may have otherwise given up on it? I think that's a big question. You're gonna see. You're gonna see, right? If they roll this out, you are going to see them like people posting online all the side by sides. I asked Siri this, but I asked Chachi and I asked Chat, GPT and I asked Claude and here's all the answers they give you, right? So like it's gonna find itself stacked up against the competitors no matter what, so it better have done the work beforehand, is what I'm saying. And that's where I remain very, very curious whether or not they're actually gonna be able to do that. Because, you know, if they're not sitting there in Cupertino right now running their own, you know, model up against all the models that are kind of the state of the art, then what are we even doing here?
Micah Sargent
Exactly. What are we even doing here?
Dan Morin
Tomorrow morning is knocking. Stock your fridge now. How about a creamy mocha Frappuccino drink? Or a sweet vanilla smooth caramel maybe? Or white chocolate mocha, whichever you choose. Delicious coffee awake. Find Starbucks, Frappuccino drinks wherever you buy your groceries.
Micah Sargent
All right. We will of course be covering WWDC when it happens, so be sure to tune in for our live coverage if you're a member of the club. If not, join the club so that you can watch us cover it and we'll Talk more about it on Future episodes of iOS today as well. In the news, I wanted to mention that ahead of the wwdc, Federico Vitichi of Max Stories has announced and launched a tool called Shortcuts Playground. Shortcuts Playground is a plugin available for Claude Code and Codex and it is supposed to do kind of what Dan was talking about. Shortcuts is kind of complicated at times and of course there are so many different tools that are out there. And what it does is it lets you say, here's what I want you to make and then it makes it. So an example was say, this is a good one. Save where I parked now, then later guide me back to my car, which made a parked car shortcut and that parked car shortcut. Well, excuse me, it's. How do I see it? There's the three dots. First it lets you. It pops up with a menu location, Save my location, find my car or Clear location. It will save the location by getting the current location, putting all of that information in and then find my car, will pull from that, that, that saved text file and then give you directly in Apple maps directions to the car and then of course Clear location essentially deletes that text file that was there, all just by typing in Save where I parked now, then later guide me back to my car. There's also one Clean this URL and strip out tracking junk before I share it. As you can imagine, it goes in and does that as well. Very cool. And I have not had an opportunity to use this yet. Macstories.net shortcuts playground but I am curious. Dan, have you had an opportunity to try this yet?
Dan Morin
I haven't. I don't, I don't subscribe to any of the AI tools necessary so. And I remain somewhat wary of installing their apps on my Mac. Maybe that's being paranoid. It seems very clever. I've known Federico for a long time. He is single minded in his devotion to, you know, taking a project and just like following it through to its furthest possible, you know, eventuality. And this seems very much a hidden him project and it's incredibly ambitious and clever. I expect nothing less from him.
Micah Sargent
Absolutely. All right, that is the news this week. It is time to move along to our app caps. These are the apps or gadgets we're using now or have been using for some time that we think are great and therefore want to share with all of you. Dan, tell us about your app cap pick.
Dan Morin
Yes. I recently was traveling overseas and I needed a new adapter to plug Things in, I have like, you know, a bunch of those little plug adapters, but they're always so fiddly and I wanted one that kind of, you know, dealt with a lot of different common plug types. And so as I was looking around I stumbled upon the Anker Nano travel adapter. I love this thing. It's very small. That was kind of my biggest feeling was I saw ones that were advertised or like recommended in other places and they're these big huge blocks. But this one's actually actually pretty small and flat. It's not that much bigger than like power adapters were a couple years ago, honestly. And it has several of the most common adapters including ones that I needed on my trip, which include like the European adapter and then the UK adapter. It has a plug pass through which is also nice. If you just have a standard two prong plug that you need to plug in, you can just do that. But it also, because it's Anker and they love everything USB and charging, it has a pair of USBC ports as well as a pair of USB A ports. So you can just use it directly like that. Like it's just a USB power adapter. So I use this to plug in my Apple watch and my iPhone overnight and charge them. I use it various times to charge other things like my kids baby monitor that we brought or an iPad that we brought. It's not the beefiest charger around. I think it only goes up to 20 watts, but you know, that's fine for charging my phone overnight. And because it's so much smaller I could just throw it in the bag. And it was simple, it worked great. And all the little pins, it's very satisfying. They all retract. They have a little like a little slider on the side that pops out the right pins. I don't know, I just, it was very tactically satisfying as well. So you know, I, I, I really recommend this. I thought it was a huge improvement over the classic terrible like, like clunky power adapters that I'd used.
Micah Sargent
Nice.
Dan Morin
It's cheap too. I will say it's like 20, 25 bucks or something. I mean like it's not, it's not crazy expensive and you're gonna spend that much buying all the different adapters from the different companies that you, you know, you need to do that.
Micah Sargent
I, yeah, I love, love what Anker offers and especially when it can be kind of that, that thinner. Yeah, they're just very clever. Their designs are very clever. The app that I want to mention is called Cassette Home Video Player. I'm not going to demo it because it would require showing a bunch of like personal videos of friends and family. But the the app is a pretty clever little thing. It's cute. It basically organizes your entire library of videos by year and makes them like their little vhs. So you tap on a year and it takes that little year VHS out of the cassette sleeve, pops it into the cassette player at the top of the app and then plays it back and you can hit shuffle so you can end up watching videos that you maybe haven't seen in a long time. It has a cute little filter that lets you add a VHS look to things. And so it's a little bit of nostalgia. But what But I ended. The reason why I ended up sharing it is because I have taken video over time at different points, some for good reasons, some as part of a review, some for no good reason. And being able to just hit that shuffle button and look back and go oh, I forgot about that or what in the world. Why did I. Oh wow. And then have a la. Just. I was going between these different modes and it was really quite a delight. And so if you're looking for a way to kind of rediscover content, rediscover memories that you've had, then this is a great way to do it. Cassette Home Video Player. Shout out to the creator of this app because I really quite liked it. Alrighty folks, if you have apps that you would like to tell us about, if you have gadgets that you would like to tell us about, or if you have thoughts, questions, etc. Email us. IowaD WWIT TV. I also want to remind you all about Club TWiT. TWiT TV. Club TWiT is where you go to sign up $10 a month, $120 a year. You can also use that QR code in the top corner there to get to the necessary site. In doing so, you will gain access to every single one of our shows ad free. That's right, it's just the content. You also gain access to some special feeds that are yours and yours alone, including a feed that has our live coverage of tech news events. So we recently covered Google IO. We'll be covering wwdc. We also have a feed that has behind the scenes stuff before the show, after the show and a feed that has our club Twitch shows. So my crafting corner, Stacy's Book Club, the the AI User group, as well as my upcoming media club, all of that is in the Club and part of that feed. You'll also gain access to the Members only Discord Server. A fun place to go to chat with your fellow Club Twit members and those of us here at TWiT. If you'd like to join, remember Twitter, TV Club TWiT? We'd love to have you. Dan Moran thank you so much for being here this week. If people are looking to follow you online and check out all your great work, where should they go to do so?
Dan Morin
Well, you can find me on most social media as D. Moran. Just give me a search. If you'd like to see everything I do, including the podcasts I do, including Clockwise with Micah every Wednesday over at Relay, you can go to my website dmorn.com you also find links to all of my novels, science fiction, fantasy. Go buy some pre order my next novel which comes out in November called Eternity's Tomb. You can find all the links at my site dmorin.com again
Micah Sargent
beautiful. If you're looking to follow me online, you can find me at Micah Sargent on many a social media network. Or you can head to Chihuahua Coffee, that's C h I H u a h u a where I've got links to the places I'm most active online. Thank you so much for being here with us this week. We'll be back again next week for another episode, but until then, goodbye. Bye.
Date: June 4, 2026
Host: Micah Sargent
Guest: Dan Morin (Six Colors)
Main Theme:
A deep dive into expectations for Apple’s upcoming Worldwide Developers Conference (WWDC), focusing on rumored iOS 27 features, especially AI and Siri enhancements, design changes, and Apple’s approach to privacy and on-device intelligence.
This episode prepares listeners for WWDC 2026 by exploring the most anticipated software announcements, potential hardware surprises, and how Apple’s AI ambitions are expected to unfold. Micah and Dan balance tech optimism with a healthy skepticism shaped by Apple's recent track record, particularly around Siri and AI.
Timestamp: 02:09 – 04:34
Snow Leopard Reference:
Dan explains the reference to macOS Snow Leopard, a release focused on refinement rather than new features:
“It lacked some of the marquee features, I think, because a lot of it was focused on under the hood improvements…”
– Dan Morin, 03:22
Expectations for iOS 27:
The consensus is that while there is talk of a maintenance release, some new features—especially AI-related—are still expected.
Timestamp: 04:34 – 08:40
The Promise of a Smarter Siri:
Micah and Dan recount Apple’s repeated claims of major Siri and AI improvements, centered on “personal context” and deeper device integration.
Past Announcements vs. Reality:
“Siri with personal context…was never demoed as far as I know to anybody outside of the company, including myself…I never saw it and is widely considered to basically never have worked.”
– Dan Morin, 06:03
Skepticism About Delivery:
Dan explains how these unfulfilled promises have led to lawsuits and skepticism, emphasizing the pressure on Apple to deliver this year.
Why Apple’s Integration Is Unique:
Micah points out first-party access as a key differentiator for Apple compared to third-party apps like Gemini or Claude, but notes the limitations of third-party access and privacy concerns.
Timestamp: 09:55 – 10:46
Apple’s Privacy Angle:
Dan details Apple’s pitch—on-device processing with a fallback to a “private cloud compute” for heavier work, aiming to balance capability and privacy.
“We have worked really hard to create a cloud system that is secure and private…your data will not be shared outside of that and you will get the results back.”
– Dan Morin, 10:17
Timestamp: 12:57 – 14:28
Smarter Contextual Actions:
Potential Siri upgrades would allow it to see what's on screen and perform relevant actions, e.g. adding addresses from messages to contacts or sending photos—moving closer to an “agentic” AI.
Timestamp: 14:28 – 19:52
The Compelling Argument:
The hosts debate whether system-level access and privacy focus will make Apple’s AI appealing compared to ChatGPT, Claude, or Google’s integrations on Android.
“If it doesn't work well then nobody will use it…training people that it is more capable now than it used to be and encouraging them to try those things. After years…where they shy away from that because it isn’t.”
– Dan Morin, 16:39
The Privacy vs. AI Tension:
Apple’s identity is rooted in privacy, but AI thrives on data. The hosts wonder if Apple can square this circle.
Timestamp: 19:52 – 26:05
Built-in “Grammarly-style” Writing Tools:
Micah is wary of intrusive AI suggestions, especially if they eat into screen real estate.
“What if that changes from what it is now to something that is more sort of AI, modern AI driven. And that is concerning.”
– Micah Sargent, 21:11
Photos App and Camera Enhancements:
New AI features like “Extend,” “Enhance,” and “Reframe” bring Photoshop-like abilities natively, though reliability—especially on-device—is a concern.
Shortcuts with Natural Language:
Dan is intrigued by potential improvements that would let users create automations just by describing what they want, but raises doubts about whether this will address underlying platform limitations.
Design Tweaks:
Expect new animations and a “Liquid Glass” look, plus convenience features such as “Create a Pass” in Wallet, and enhanced satellite functionality in Maps and Messaging.
Timestamp: 26:05 – 27:04
Siri As a Standalone Chatbot:
The possibility of a dedicated chatbot app for Siri could entice lapsed users—but Apple’s offering will inevitably face side-by-side public benchmarks against ChatGPT and others.
“If they're not sitting there in Cupertino right now running their own, you know, model up against all the models that are kind of the state of the art, then what are we even doing here?”
– Dan Morin, 26:58
| Timestamp | Segment / Discussion | |------------|----------------------------------------------------------------------------------------| | 02:09 | “Snow Leopard” update framing—maintenance versus marquee features | | 04:34 | AI and Siri: The promise of personal context and integration | | 09:55 | On-device AI, “private cloud compute,” Apple’s privacy pitch | | 12:57 | On-screen awareness, App Intents, and agentic AI | | 14:28 | Will Apple’s AI integration offer a compelling alternative to ChatGPT/Claude? | | 19:52 | Rumored Grammarly-style writing, Photos/Camera AI tools, and Shortcuts improvements | | 24:28 | Design changes, Wallet/Weather/Satellite upgrades | | 26:05 | Will Siri as a chatbot entice users? Will Apple’s models compete with market leaders? |
Micah’s Playful Skepticism:
“Siri—Ah, very good.” (08:58) Micah gently lampoons Siri’s past failings, reflecting general user sentiment.
Dan’s Travel Tech Pick:
An unusual “app cap” segment features Dan’s glowing review of the Anker Nano travel adapter, which he describes as “very tactically satisfying,” (31:13) blending his love for gadgets with practical travel tips.
Micah’s Nostalgic App Discovery:
Cassette Home Video Player: An app that organizes personal videos into virtual VHS tapes by year for a shuffle of old memories (33:05).
Apple’s WWDC 2026 is viewed with a mix of hope and caution, particularly around long-promised generative AI and Siri upgrades. Despite years of announcements, the consensus is Apple must now deliver, not just market, next-level AI.
Privacy remains Apple’s ace, but also a constraint in matching competitors like Google. The effectiveness of “on-device intelligence” and secure cloud processing will be a major test.
Expect improvements in design, Photos, writing tools, and automation, but the star is whether Siri and system intelligence can finally “just work” — and match runaway AI leaders. Apple's upcoming announcements will shape not just user experience, but broader industry faith in Apple as a consumer AI leader.
Next Week:
WWDC coverage and real-world reactions to whatever Apple actually delivers!