Hello and welcome to Connected episode 536. Today is January 22nd, 2025. The episode is made possible by our sponsor, Ecamm. My name is Stephen Hackett and I have the pleasure of being joined by our keynote chairman, Mike Hurley.
Hello, thank you, Stephen. And I, as keynote chairman, have the pleasure of introducing to the show annual chairman Federico Vatici. Hi, Federico. Oh, hello, fellow chairman. How are you? And hello also, the other one, Stephen. Yes, Stephen. Co-host Stephen. Yes, co-host Stephen. Yes. So on last week's pro show...
which you can get by going to getconnectedpro.co and you can sign up, support the show. You get longer ad-free episodes of the show each and every week. Me and Federico were way too excited about the possibility of a Nintendo Switch reveal. It didn't go the way that we expected, but it did happen. So Nintendo put that out and I thought we could start off today's episode by some vibes. Steven, are you at all aware of what happened in any possible way? Yeah, no, I watched the video. I noticed it was two minutes and 22 seconds long.
You guys catch that? Huh? I actually didn't. I knew it was like two minutes, but I didn't know it was 2.22. Very clever. That's fun. No, it looks great. Bigger. I'm excited for bigger Joy-Cons because the current Joy-Cons are like little, they're for children. Yeah. I hope they fixed the...
Drift? The Drift issue? I don't know if they did. Yeah, they did. We assume they did. They made a big point in the video showing the Joy-Cons spinning around. That would suggest to me, and I'm sure Federico would agree, that that is some kind of hint to them having done what needs to be done, which is something called Hall Effect. It's a different type of technology for sticks. The assumption is that they would have handled that. Honestly, Nintendo always does weird stuff.
I 100% expect they would have fixed this because this was a problem for them in the long term. They had to do a lot of replacements and stuff. My original Joy-Cons, one of them died and I got in touch with their support. Anyways, it's the whole thing. So bigger, hopefully more powerful. There's like a mouse mode or something. That's rumored, right? Because they had that shot where the Joy-Con, which is magnetic now, it looks like, which is awesome. I hate the little track thing you have to slide in and out. Some sort of cursor.
mode or something that looks interesting that is the expectation what that means if anything we don't know right like will you play call of duty like that way who knows you know maybe what do you think federico about like the mouse thing i do think it's real and happening and a way for nintendo to to have a an interesting answer to the steam deck in terms of
Here's another environment where indie developers can port their PC games to a handheld. This handheld, so the Steam Deck has a touchpad. And it's maybe you and I, you know, the games that we usually play, we don't rely on the touchpad a lot, but there's other types of games. And obviously there's a Civilization 7 coming out this year that absolutely benefit from Pointer.
And I think it's interesting to see Nintendo sort of going after that part of the Steam Deck without a touchpad, but by saying, well, the Joy-Con is now a mouse. And obviously, in addition to that, I'm sure there'll be some weird Nintendo gimmick, like a new Mario Paint or something that takes advantage of a cursor. Yeah. So it's a podcast assistant to a kind of funny games cast, and they were given their predictions over the last few days or whatever. And one of the things that...
One of the hosts said, what if Mario Paint is a part of Mario Maker 3? Which I thought was a really interesting thing to do, to combine that idea together. If this is the weird thing they've done, great. Because it's not going to affect me at all if I don't want it.
There are a bunch of weird things Nintendo could intend to do and adding in this support, isn't it? And like, you know, it's not a problem. The magnet thing, I'm really intrigued to see what that experience is like of actually attaching and detaching the Joy-Con. But yeah, I think pretty much anything could be better than the way that you currently have to do it with that like really impossible tiny button.
that's on the back of them. And you can, if you have children in your household, you will discover that it's possible to jam a Joy-Con on the wrong way around to a restaurant. You don't need to have children to do that. You could also have someone who did that on the first day, which was me. And potentially new Mario Kart, finally. No, not potentially. That's a new Mario Kart. There's no potential. I'm excited because my Switch, my kids play several things on it. It's hooked up to the TV like 98% of the time. But I sometimes, you know.
Dad draws a bath and plays Mario Kart. No, I'm just kidding. Not in the bath. But you know, sometimes I'll play Mario Kart. So I'm excited for a new one. Everyone likes Mario Kart and that's why they showed it in the trailer. You know what I mean? Everybody loves Mario Kart and they're going to make a new one, which is going to be amazing because it is actually the first new Mario Kart in such a long time. Since the Wii U, right? I mean, since the Wii U. It's like an insane amount of time since the new one. So I expect big things from that.
So yeah, I'm really excited about this. The only thing that's a downer for me is that it's not coming until way later in the year. I'd hoped that this thing was going to come in March, but it's probably June or July. That's a bummer. I'm bummed out about that. Excited about the rest. I suspect there'll be one under the Christmas tree this year at my house. Oh, yeah. I mean, do it. Federico, you have solved email.
What's going on? Well, no. No, I mean, no in the sense of like Federico. It really is thanks to Mike. Hello. And so I got this text from my fellow chairman. Wow. A few days ago. Saying, hey, have you ever played around with this? Because I was talking to a friend and...
They've been really happy with it, and they've been doing some incredible things with this app. So this app is called Shortwave. I was familiar with Shortwave. I think I tried it when it first came out. It was like this Gmail-only client. And it was like, at the time, if I recall correctly, it sort of looked like a modern version of... Do you guys remember Google Inbox?
That old... Yeah, it kind of looked like that. So that was a couple of years ago, I think, when Shortwave came out. And I kind of lost touch with it. It now seems that over the past few years, they have sort of become a more business-oriented product. And they are going very heavily, very all-in on AI integrations. And so I thought, well...
Mike gave me some examples of what their friend had been doing with shortwave. And I took it for a spin. And all this to say, I canceled my superhuman subscription. And I think this product is incredible if you receive a lot of emails. And especially if you like to receive everything at a single address, but require better organizations.
the different kinds of messages that you get. So the idea here is that like in Superhuman, in shortwave, you can create multiple split inboxes. The feature is literally the same. You can take advantage of Gmail's own default organization. So you can have emails fall under like promotions, updates, finance, those sort of like default categories. Or...
you can make your own splits like in Superhuman. And a split can be based on any kind of possible like filter or search query or label. Like you can make a split out of anything you want. What I think is interesting is that this shortwave still carries over like some of the legacy of the old Google Inbox app in that you can choose to have some emails.
be bundled together and appear as a small bundle in the main inbox. So for example, I have all of my emails about something that I purchased. I automatically labeled them, and I'll get to this in a minute, I automatically labeled them as transactions. Those transactions emails appear when a new one comes in as a small bundle.
in my inbox called transactions which is very similar to what google inbox used to do and to what other i i think back in back in the day i think when i was using hay many years ago um yeah um i think that there was also a feature there uh so this is still supported here the ai stuff is the best i have found to date uh both in terms of
The stuff that I don't necessarily really care about a lot, which is like there's a feature, there's actually a collection of features to write emails in your style because this service can be trained optionally if you want on your data and learn how to write emails like you, which is not something that I necessarily want or need. But if you do want that. But if you do want it, I tested it.
sort of eerie how accurate it is like it picked up my style correctly and you can refine like if you see something that like okay this sort of kind of sounds like me but there's a sidebar where you can talk to the LLM and you can say no actually make it sound shorter and so you can tweak it with natural language and of all the
this kind of similar products that I've tried, this one is the best. I am more interested in the AI enhancements in terms of search and inbox organization. And this is where I think Shortway really got me. So the search, I actually sent you a few minutes ago an example. We were talking in the pro show about wallpapers. And I recalled that I had purchased over the past couple of years,
a series of wallpaper packs from Gumroad. But I couldn't remember off the top of my head what were they actually called, what the name of the different creators on Gumroad was. So I asked in the AI sidebar of Shortwave, can you find the wallpaper packs that I bought from Gumroad? Like a natural language query. And he found...
a list of all the transactions for the wallpapers, extracted the names of the wallpapers, the names of the creators, and it linked me back to each email for those purchases so that I could also redownload them again. And this is just... That's great, man. It's incredible. You can go much deeper with this in the sense of like, I have been able to ask stuff like,
Can you look at emails that... Oh, actually, John. John is also checking this out. John sent me an incredible example today that I'm going to read you. John asked, find messages received in the last 30 days about new and updated apps from individual developers. Messages may include links to TestFlight and promo codes and have links to press kits or links to the same. Do not include any messages that have an unsubscribed link in them.
And the AI responded with a list of indie apps that we were recently sent with details for each app and a link back to the original email message. I did something like, a couple of days ago, I asked, can you look in my email for Club Mac Stories support requests that I haven't answered? And each one of those, can you make it a to-do for me? And it worked.
This to-do functionality, unfortunately, is proprietary to shortwave. So it's tasks within shortwave. I wish that there was some kind of like to-doist integration, but there's not. But there's two more things I want to mention. The other AI feature that I think is like my favorite so far in any product of this kind is AI filters.
Obviously, I'm really into like smart searches, filtering criteria for all kinds of productivity apps. But usually you got to learn the syntax. Gmail does have a syntax that you can learn. And it's a pretty complex one. And I don't want to learn it. So instead, I am using... There's this feature where you can write your own AI prompt. And when a new message comes in...
So shortwave is going to match it against the AI prompt. And if there's a match, it's going to do something. And in my case, it's applying labels. For example, I have a filter called shipped.
And this is what it does. Include emails that are shipping notifications for physical products or goods that have been shipped to me. These emails may be in Italian or English. Include emails for all stages of the shipping process, from the initial shipment to tracking number to the item being delivered. Never include receipts about the initial transactions. I only want shipping confirmations and updates. Now whenever I get shipped something, and the emails may be formatted in a whole bunch of different ways, right?
they may be in two different languages, it's going to be consistently tagged for me. Because that's not really something you can do with Google. You can't get Google to do that because it needs the... If everything came from one email address that you could do with Amazon, you could maybe do it with Shopify, but you can't guarantee every purchase you make comes from one of those places. I purchased that iPhone case that...
John reviewed on Mac stories today. Like that came from a totally different Shopify store. Like how would I consistently automate this stuff without this kind of AI integration? I wouldn't be able to do that. Lastly, I will mention, and this will be part of a story of an article that I'm working on. On the iPad, this is the best PWA that I've ever tried.
It's the absolute best progressive web app I've ever seen. It even supports PWA push notifications, which is something that I think Apple added like last year. I haven't seen anywhere. So they have done a really good job with their progressive web app. It supports custom keyboard shortcuts, push notifications. Really well done. Because as is the case, and this is something that I will...
explore more deeply in my story, there's this clear divide now between the functionalities and the UIs of native iPad apps compared to what you can get by using the web app counterpart instead. So yeah, thank you, Mike, for the recommendation. Pleasure. The pitch that this friend of mine gave for why they like this app, which I just thought I would share, was like they...
Basically, they asked the AI, give me an itemized list of every action item for my kid's school and put any calendar events on my calendar. And it just went, boom, did it all. And he was like, I'm in. So I heard it too. I was like, I love the sound of this. I mean, my problem is, as it always is, some of my email.
is not Gmail. Like one email account that I use a lot is not a Gmail account. It's my iCloud account. And like they just don't support iCloud. And so it's like, well, which is usually the way these things go. But I'm happy that these tools exist in these ways. I think this is email. Email to me feels like a prime candidate for AI. Not the doing of it, but the handling of it. Yeah.
The idea that the entire world can just send you stuff, anybody can get into your inbox. That is just a wild system that we have accepted as a species. And something that can help you manage that is perfect. That is how we get to a better living with email life. So I think tools like this sound fantastic to me. Yeah, pretty good.
It's expensive, but it looks like all of this email business-oriented AI power tools are expensive. You're on the bleeding edge, right? And so you've got to pay for it. And eventually, if it works out, it won't be so expensive anymore. Yeah. Well, I'm happy you like it. I'm very keen to see how it goes to you over the long term. Yeah, me too.
I'm still using MimeStream. Again, Gmail only, so Mike doesn't help you. But I'm still really happy with it. And they have said that the iOS app is coming along. He had an update on Massadon the other day. But there was also reporting that the categorization stuff that's, for some reason, only on the iPhone and iOS 18 is going to come to the iPad and Mac. And Mike, I know you've talked about it. Are you actively using that feature?
Yes. And how has it been? In the past, I kind of just don't like that stuff, but how's it going? I think it is. I mean, people seem really mad about it, and I don't understand. I just think it is, like, fine, and that's all I need. I just want emails from people.
in my inbox and then everything else somewhere else i don't care where it goes just get it out right like yeah they have like these three categories it doesn't really bother me like just just get it out now the feature that i don't think is implemented very well is apple's attempt at trying to surface important emails like that is a separate thing they're doing that is bad like they've not done a very good job of that feature because on two occasions now i've had like spam scam emails
highlighted to me as an important thing that i need to know about wow like you got to change your netflix password but it turns out it didn't come from netflix so it's like no it's fine you know click on that it's cool not not awesome really because like that that does not that is not a good pattern because you are like people trust their trust apple in that scenario so like a different person if they got that would be less likely to check if it was spam or not
So that is an unfortunate scenario. But the categorization works well for me. And I want it on my iPad and on my Mac. Because at this point, the only thing I am still using Spark for is just to have some element of categorization. You know, newsletters go into a newsletter. Transactions go into a transactions. And that's the end of it. And so once they bring it, I'm done with Spark. Okay. I'm glad we could talk about email. Feelings about email. Love email.
Do you? No, but I love talking about it. I hate it, but I love talking about it. It is evergreen podcast content. Yep. This episode of Connected is made possible by Ecamm. Ecamm Live is the leading video production and live streaming studio built for the Mac. But it doesn't stop there because Ecamm is great at simplifying your workflows.
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That's ecamm.com slash connected. E-C-A-M-M. Ecamm.com slash connected for a whole month of Ecamm Live for free. Go there now and check it out. Our thanks to Ecamm for their support of the show. iOS 18.3 incredibly has reached release candidate. It's like, oh. What is even in it? There's, I think, two features.
There was kind of nothing. And then right at the end, they put a bunch of stuff in or changed some things. Basically, the biggest two things in iOS 18.3 are Apple intelligence related, but no features. So first off, iOS 18.3 enables Apple intelligence by default at upgrade, which is an incredible decision. Like just a I don't even know why decision.
It's no longer opt-in. It is still classed as a beta. And if you don't want it, you have to go into settings and disable it. So you're told it's happening. You're allowed to customize it in the way that you want to. Maybe you can skip it. I don't know. I have not done an update from a non-Apple intelligence device. But it's part of the, hey, you've upgraded. You now have these features. So it's like...
Kind of how features get added to the operating system, right? Typically, you don't like opt in. You're not like, oh, I want to opt into the new home app. No, you just get the new home app, right? So they're doing that. But Apple Intelligence, that's a stretch. I mean, especially because it is still a beta. I mean, especially when iOS 18.3 disables some things.
News and entertainment apps will no longer have notification summaries, and they've also italicized the notification summaries, which I hate. I think it looks so bad, but they've done it. But at least you can't not notice it. You do notice it, but yeah, they've done that. They've also added two features to visual intelligence, which is everyone's favorite feature. So if you use visual intelligence now, you can add an event to the calendar app.
So you've seen a poster and you're like, oh yeah, I want to go to that. You can also more easily identify animals and plants, which again, so if you don't necessarily have to ask what is that dog like they did in the ad, it should just now show you what kind of dog it is. That video still cracks me up. Ask the person holding the other end of the leash what the dog is. All of these two features, they are steps in the right direction for this feature, right? These are things.
that it should do. So great, they're adding them. The idea of visual intelligence is more interesting to me than the actual implementation of it so far, but it's like, we'll see where that goes. But yeah, iOS 18.3 doesn't have anything new in it. So I guess now we look towards iOS 18.4 as a potential for the rest of Apple intelligence, right? Personal context,
App Intents. This is all supposed to be a part of iOS 18. There's probably some other stuff I don't remember. There is none of that in .3. And I expect, you know, if this comes out maybe this week or next week, then maybe the week after, the .4 beta will come out and it will have, I would expect at least something. But really, iOS 18.3 is a release where Apple has kind of had to take a step back.
from something in Apple Intelligence, which is the way that the notification summaries are working because people are getting real mad. And a lot of news organizations are very upset, I think for good reason, because it's making them look like fools. And so now they're going in and they're changing it. So weird release. It's just like a bug fix release, which is usually not a problem for a 0.3 or whatever, but...
There are still a bunch of features left and we're five months away from WWDC. There's a lot to go. So good, good work. Good luck over there, I should say. Good work too. Yeah. So there we go. I'm super excited to install it. Can't wait. Can't wait to do it. I have a story. I'm so excited for this. There are so many notes in Notion and I've not read any of them. It's almost a thousand words for the things.
I don't want to know. I don't know what happened. I want to know now. It's like a blog post in here. Yes. Stephen's blogging inside of Notion. I was live tweeting as it was happening just into Notion. Okay. So last, was it last episode? A couple episodes ago? Yes. We spoke about tech things we wanted to do in the new year, right? Sure. New year's resolution. My resolution's 5K.
Sorry. I think you mean a yearly theme. Yeah, my yearly theme is 5K. It doesn't have the same ring to it, does it? So one of the things that I spoke about was file management. And I mentioned that we were bumping up against the two terabytes that we have on iCloud. So we have an iCloud family, my wife and I.
We have three kids. Two of those kids have iPhones. Third kid has an iPad that is basically just a video game and a math homework machine. And so we've got a shared photo library. The shared photo library has just crossed one terabyte in size, which is wild. And then, of course, the kids have their own and device backups, all that sort of stuff. It's like, well, I need to address this.
I said this and lots of people, and I appreciate the feedback, said, hey, you don't have to go to six terabytes. There's this option where you can upgrade and add an additional two terabytes. So you'd be at four terabytes total for an additional $9.99 a month, as opposed to the $29.99 a month, the six terabyte cost. This is literally what I wanted to do a few days ago. Oh my God.
Okay, so you're adding two terabytes on top of your current two terabytes for four terabytes total. And it was how much a month? Like $20 a month? An extra $10 a month. Okay. On top. On top. Six terabytes is $30 a month, which is a little more than twice the cost. So it's like, great. I'll just add two terabytes. I'll just kick the can down the road. And maybe by the time we hit four terabytes, you know, maybe...
One of the kids will be off and they'll be, you know, out of the iCloud family doing their own thing. So I go to settings. Do kids ever leave the iCloud family? I feel like they don't. I mean, maybe eventually. It's like when they leave the cell phone plan. You know, like, I don't know. First time parent of teenagers. Do they need their own family for that? Maybe. I don't know. You'll find out. Let us know. Also, I find it a little frustrating that you can only have six people in an iCloud family plan. Oh. So that's important.
I'm going to come back to that. Just stick that behind your ear like a pencil. Or a piece of gum. Cigarette. Whatever. So go to settings. I do not have this option. I see two terabytes and I see six terabytes. This upgrade options. And I'm going to put a screenshot in the show notes that our friend Casey Liss, he was listening to the show and sent me this.
I was like, oh, just hit this button. I was like, yeah, I don't have that button. That's the problem. And I figured, well, you know, probably something weird going on. I'll deal with it later on. But then over the weekend, I don't know what happened. Actually, I do know what happened. My wife and one of our kids was out of town and we hit the two terabyte limit because like they were out of town doing a bunch of video stuff. That's so good. Hit the limit.
I'm like, well, I don't have time to deal with this today. I'll do the six terabytes. I'll do this temporarily. And then when I get some time, I will deal with it. So this is moving up to the six terabyte monthly plan. Yeah. So now I have six terabytes total. It's way more than I need. It's more than I want to pay for. Mike, I put a URL to the image in the Notion for you.
And I was like, well, I'll just, I'll deal with it later. So it turns out later was only one day because I ended up having some free time on Monday. I was like, well, I'll just chat with AppleCare and they'll fix it for me. So contact Apple support via online chat. They initially said that upgrading like this wasn't possible, that it was two terabytes or six terabytes. There was no upgrade option.
So I had the screenshot from Casey. I dropped it in the chat. I said, hey, I get that, but it does seem to be an option. You know, this is from a friend of mine. And so I don't understand like why I don't have it. They asked if I had family sharing on, which I confirmed. And they said, well, you can purchase an additional two terabytes on another person in your iCloud family. And that space will be basically donated into the family pool.
I was like, great, that's not what Casey did, but, you know, if it works, it works. Why can't you do that? Well, just hold on to that too. I mean, I'm just on this ride with you, by the way. Put that behind your other ear. You're getting, Mark will have so many ears by the end of this. I know. I'm just, you know, we're on this ride of use, you know, so I'm like upset on your behalf. So I grabbed Mary's MacBook Pro and I buy two terabytes of space as her. Now, the space does not show up.
in the iCloud family. So you're doing this while you're still in the active chat with the representative? And at this point, I start live tweeting into Notion. Because like, oh, this is something that's happening here. So I asked the person, hey, there's not, I don't see any UI to like donate this space to the family. Nor was that a term that I was familiar with. And remember, dear listener, I do this for a living.
Apple tech support. Yeah. I mean, I'm on a podcast called Mac Power Users. I'm not unfamiliar with how these things work. Did you say that to the person at Apple? I did not. I don't think you know who you're dealing with here. Did you know I used to be a genius? I'm a Mac Power User. I could fix this if it was mobile me. That's how old my shirts are. At this point, I hear boop boop, and the chat has just switched to a new person.
The person didn't tell me they were sending me somewhere else. Just a new person comes up. Well, it's because you've become a problem. Yes, I think. They've escalated you. I have been escalated. They verify my identity with a push notification because this person is going to look at my account and see what's going on. They see the six terabytes and say, oh, I can just downgrade you to four.
I was like, great. Maybe the UI isn't showing up for me for some reason. Now I have looked at my phone and my Mac at this point. I was like, great. If you can just fix it, that's fine. And if I ever need to go above four, then I'll just go to six on my own. And then the chat goes quiet for a little while. Like, okay, there, you know, I'm sure they're helping more than one person at once. It's Monday. It's a holiday. They're probably, you know, busy, whatever. And they say, hey, to do this, I need you to log in and downgrade.
All the way down to the free five gigabyte plan. This is terrible. Because the way iCloud billing works is you have the amount of space you pay for until the next billing cycle. So you'll have your six terabytes or whatever until, you know, the 18th or whatever, the 19th, whatever it was. And then they say, is there anything else I can help you with today? I'm like.
whoa, we didn't solve anything. We're not done. All you've done is you've downgraded me from six terabytes to five gigabytes. And I'm pretty sure that's going to be a problem in, you know, 24 days or whatever. Yeah, but is there anything else that they can help with, you know, while we're at it? Yeah, one of my HomePods is buzzing. Can you help with that? And so I'm just like, no, this is not fixed. Like, we haven't done anything. So then...
They say, let me explain it to you. And then they say, I'll be right back. And I'm just like, on hold again. It's like, checking my email, you know? And then they say, hey, we need to escalate this to a senior advisor. Can they call you? I'm like, yes, absolutely. You know, here's my phone number. What is this chain of command here? I don't know. This is absurd, right? Like, you're done. Okay, no, I'm not.
Well, then somebody else has to step in. Yeah. It's very strange. So here we are. Can they call you? I'm like, great. And then the person, the chat person says, they can call you right now if that's going to be. He's like, yes, great. I'm at my desk. Like, let's do it. The phone calls. It always makes me laugh because AppleCare in the US, a lot of it's in Austin, Texas, and their area code is 512. And so I just kind of get a little chuckle. You know, it's like, because I have a website.
Those digits. Do you ever tell them that? I did not. I should have said, look. Hi, I'm a Mac Power user and my website. Have you heard of Performa Month? That was me. That was a big deal. I know it was a big deal around the water cooler. It was. That was me. I did that. So get on the phone. And I should say, all these people, very nice. My problem has not been solved, but like.
Except the one who told you to downgrade to five years. Except that person. That person had balance in their heart. That person hated you. How can I wreck this dude's iCloud account? They were like, oh yeah, this is the Mac Power users guy. Yeah, I'll show him. Put your photos back on Dropbox, you know? So the person on the phone said that having two terabytes and upgrading to two more terabytes
is not a feature that's supported and that they don't know what image I saw, but it's not possible. The plans are two terabytes and six terabytes. I'm like, well, I know that's not true, but at this point, my, uh, nerd overhead timer and timery has been running for two hours. Like, like I can't, like, I just, I'll set it back to two terabytes. I'm going to upgrade it from five gigs. I'm going to set it to two terabytes.
Um, cause I still have the six until the end of the month. And like, I will call Apple care in a couple of days and like sort it out. So I was told the guy was like, Oh, okay, thanks. I'll just do six terabytes. Like just to get off the phone. And that guy was pretty short with me. And I, that was reflected in my feedback that I gave, you know, they send you like a thing. I don't want to get anybody in trouble, but like he was just rushing me off the phone. So.
I was like, well, I'll deal with this in the future. We have information that you believe to be incorrect as well. Yes. That I know is incorrect. Because my email and mentions have been full all week of people telling me, just go to four terabytes. Which, again, I appreciate. Somebody emailed me with steps how to do it. Awesome. Thank you. So I hang up the phone. And at this point, I'm a little mad. I'm a little upset. And then I had my brain wave, gentlemen.
It was like lightning struck my brain is how this felt. Okay. The plus two terabyte option is only available if you have Apple one, which I do, right? I don't pay just for iCloud. I pay for Apple ones because news plus Apple TV plus fitness, all that stuff. Right. But I use a separate Apple ID for purchases than I do for iCloud.
I feel like at this point, all my blame has moved to you. There's more Apple blame coming. Okay. My Apple One is owned by that account, not my iCloud account. And that account is not part of my iCloud family. Stephen, what was the problem?
why is that why would you do that because at some point i changed the apple id i was using but all my purchases were like lots of people do this like it's very common you walk me through that one more time so my my i'm calling it legacy apple id just like just so we can talk about this um i also renamed it legacy steven so i could tell the difference between the two of them now that is with an old mac.com email address
that I didn't want to use anymore. This was when I was using iCloud for my email. And so I signed up in the mobile me era for a different email address. And you couldn't, you know, you've never been able to move purchases. And that was before iCloud family sharing, right? This is in the mobile me days. And so I, then at that moment in 2011, past even made a mistake where he said, I'll use.
My new Apple ID for all my syncing stuff, but an Apple, up until this very specific feature, supports you logging in with a separate Apple ID for purchases. It's right built into system settings until this day. You can have your Apple ID and you can have a purchase ID. We'll call it the old .Mac one. Yeah, legacy, Stephen. Legacy Apple ID. Legacy. And the MobileMe one is what you have used as essentially what is now your Apple account. Yes. Okay. But I've still been...
Purchasing things logged in as my old Apple ID. My whole family has. And I never brought that account into my iCloud family setup for two reasons. One, I wasn't sure that it wasn't going to break anything. It's like, oh gosh, if I bring this in, what's going to happen? So I've been nervous about that. How did you pay for Apple One then? I don't understand that part. The second reason is that
iCloud family sharing only has six spots and we have five people in our household. My wife and I, we have three children. I've kind of held that six spot open if like we need to bring one of our parents for some reason into it or, you know, somebody else. Like I've just kind of had it there open. And thirdly, I have, other than having to sign in to do different accounts, like one in iCloud settings, one in the app store settings.
This has not caused a problem until now. It has worked perfectly for over 10 years. Since 2011, Stephen made this decision. It's been fine. It's a little annoying when you set up a new device because you have to sign in with two Apple IDs, but it's supported. It works. But not if you want to upgrade because adding an additional
Two terabytes to your account is only supported if you have Apple One. And I technically don't because my store account does, not my iCloud account. So the thing that I'm just, I'm a little lost on, right? Sure. Yeah, this is confusing. And like, you know, people have already hung up the show, but it is confusing. The old Apple ID pays for Apple One. It's not in your family. How are you an Apple One subscriber?
It's a different person. Because I'm signed in to all the media apps. Like in system settings, if you go to settings on your phone or your Mac or whatever, there are two places to put an Apple ID. You have your Apple account and then you have media and purchases. Media and purchases was signed into my legacy account and that gave me access to all the Apple One stuff. What about your family? Same thing. They're signed in.
as their individual accounts, and then my legacy Apple ID for their purchases in media. Oh, so you're doing a really weird family sharing setup, aren't you? Probably. And I'm sure there are other people who do this, but yes, it's definitely not ideal. In theory, the kids have their own, and they can't buy anything without a push notification, and you allow it. That's how family sharing is supposed to work, but that's not how it's working in your house, right? It's working because they hand me their phone and I...
do it they they have like they have to get you to do it so they're there they have apple one because the iphone essentially thinks you're logged in yeah not because there's a family thing right that's okay and honestly because it's been working i was like i just never have to deal with this like and you didn't maybe didn't think about it when this whole process began it did not cross my mind nor this is my complaint with apple
nor did it cross the mind of any of the three people, including the senior advisor I spoke to. You must be one of the 20 people in the world that's still doing this, though. Come on. If you're still doing this, let us know. I still have these separate accounts. There you go. Yeah, but you've also done the wrong thing in asking our listeners to contact us about this. Sure. Right. Okay.
Everyone that does this is listening to this show right now. Ask on the pen addict next week and see what those people say. They won't even know what I'm talking about. We could have gotten to the bottom of this if any of those people had said, do you use a separate Apple ID for iCloud and purchasing? But they didn't. And maybe to your point, because most people don't do it. But this was my thought. I was like, oh, I bet.
Because I do this, I, for some reason, and I think it's probably a bug on Apple's part, or maybe they just don't want people to do it this way anymore. I am forbidden from this sweet two terabyte fruit. I cannot have it. So I'm like, look, I'm going to add Legacy Steven to the family. Oh my word. Legacy Steven. Legacy Steven.
That Apple ID, I changed the icon. It's my little 16-bit version of me, but on a gray background instead of the blue one. So I can like tell them apart visually. And I literally named him Legacy Steven. So it looks like you're dead, basically. Yeah. Who now can never be in my iCloud family because I took the last spot. Sorry, dad. And I guess no more kids, you know. Oh, that was already dealt with. So I add Legacy Steven. I do this by, I have a MacBook Air that I use for testing.
And so I just made a new account on that and signed that into that legacy ID like fully so it could get the invite to join the family. So I did that. It took a while for it to show up, but it did, you know, maybe an hour later. I later found a support document that I put in the show notes, but I can't find it again. That says family sharing changes may take up to 30 minutes to go into effect.
What is that? Why is that the case? But added Legacy Steven to the family. And this is when things get real weird. Upon doing that, my iCloud account now has eight terabytes of storage. It now has my six plus Mary's two that the first person had me buy. I don't know why that is.
Maybe you have to wait for the billing cycle to end, for the two terabytes to go away? Yeah, so I set it back to two terabytes, and I think next month it'll roll off, and then I can go to four terabytes. I have a task to remind me to do that next month. Although I will also get the very scary email of like, you're out of iCloud space. It was a real fun notification to get over a weekend. So now I'm in this situation. Okay, Legacy Steven is in the family. I enable all the shared purchase stuff.
So, at this point, I'm going to do it right from here on out. So, I sign out of that Apple ID everywhere. Everyone now is using their same Apple ID for purchasing and for the media stuff. And that actually went pretty well. It wasn't until that evening that any of the shared stuff worked. So, I went into the TV app.
and tried to play something out of that Legacy account, and it gave me an error. So everybody else's devices now, they're not signed into Legacy Steven anymore? Right. Legacy Steven has been deprecated. Well, I mean, he's still there, right? He's still there. He's still hanging around. And his stuff is shared into the family. Yeah. So the other thing I did at this point was, because I wasn't sure what the Apple I would do,
So I moved the Apple one purchase to my, I got account instead of the legacy one. I did not make legacy Steven, a parent or a guardian. I just made it. He's just like a regular family member. So you should, you should have asked, uh, OTJ for advice, you know, OTJ with this fake kid. Yeah. Yeah. Serenity, uh, had one for a long time too, that she made like in her eye more days, like, and you can't get rid of them.
really weird um so moving forward what is going to happen uh in a month i will hopefully be able to upgrade and have just four terabytes of iCloud space and not six or eight that i currently have which is really funny when you log into iCloud the little thing of like how much storage space you're taking mine is so funny looking because most of it's just empty um i moved the apple one over so it will expire for legacy steven and
my, you know, normal Apple ID will pick that up. And I'm also doing that with the regular, with my app subscriptions. I had a handful of app subscriptions. I'm going to let them expire and then move them over to my main account. So at the, at the end of all of this in like a year, uh, when all my, cause one of my, I forget what it was. I just had like one of my main app subscriptions. Maybe it was carrot weather, just renewed like three days before. So like in a year, all of that will be moved over. And then legacy Steven will just have our,
up to this point, media purchases, which is mostly, you know, movies and TV shows and stuff. Yeah. And that does now work. That'd be apps in there. That'd be a bunch of apps in there. A bunch of apps are in there, but I could download them. Like it all seems to be working the way it's supposed to. That all did not work the first day. It took more than 30 minutes for it to sort of settle down. But, you know, I also made a lot of changes to my accounts kind of all at once. A side effect of this.
Is this totally broke? And I probably should have seen it coming. It totally broke my music library on my devices. Yeah. No. And it seems to just be my devices. And so I'm not like tooling around on Mary's phone. Her music seems OK, but I'm pretty sure that her.
is her thing is just apple music i don't think she has any i think we like set her up a new library at some point mine has a bunch of purchase stuff from that old account and the music app is real mad about playing that now even though in theory the content should be shared it doesn't seem to work is content shared like that like music movies and tv shows are and music is listed in apple's support documents as something content that can be shared so but it doesn't seem to be working
So I was like, well, that's weird. For hours on and off, it would show loading your cloud library. This may take several minutes in the music app. It took several days. Do you remember you had to do those authorizations? Do you remember that? Yeah, you still have to do that, actually. So I wonder if maybe music, there is something weird with music. Maybe, because music, remember, is iTunes.
Yes, exactly. Yeah. I wonder if music is different to movies and TV in that way. I don't know. And Zach points out, is this pre-iTunes Plus, which is the DRM-free music? It very well could be. Man, we're learning a lot about the past today. Things I haven't thought about for a very, very long time. iTunes Plus. Yeah. Yeah. And so what I did was I took my music folder, put it on my desktop.
I was like, look, I'm just gonna, I'm just gonna rebuild it. Like, I don't think I'll ever find all the bugs in this. And so I set up a new music library. And because I had my, I had all my music downloaded locally on my Mac. So I have all the folders. So I know everything that I had. And I'm just like, you know, a little bit at a time working my way through that. I have some music that, you know, is not in.
apple music that like you know like you know i bought it off band camp or something and so i'm just dragging those in as local files and letting it sync and it seems to be working music on the mac is really buggy like trying to add a bunch of music in bulk and it just it just like gives up it's like oh no these are duplicate files or the network is offline it's like neither of those things are true you have a new music library folder and i'm browsing the internet like it's not down but i'm slowly digging my way out but it's a mess
It's a real mess. Do you wish you would have just done the six term? I mean, so what I told Mary is like, this is saving us. I mean, if this works, it'll save us like $240 a year or whatever. I've spent more money than that in my own time by now. So that's rough. That's the way. But I mean, it is ultimately going to fix my like split Apple ID thing, but I shouldn't have had to fix it. Like Apple should have this set up where I could just do it.
And maybe it would have worked if Legacy Steven had been in the family, but at that point, I was just kind of committed to, let me just actually rip the Band-Aid off. But this was no help to Apple, and if I had not had this idea strike me, who knows where I would be. But there you go. That's been the last couple days of my life, and it's real fun. What a disaster. Mm-hmm.
This is rough. I feel bad for you. There's a thing that came up yesterday. I was seeing my mom yesterday, and she's showing me her phone, and she's like, it keeps telling me that I'm running out of space in my iCloud, and I don't know what to do about it. I convinced my mom that she should pay 99 pence per month. This was a while back.
iCloud storage, right? She was on the five gigabyte free. And then I had to convince her to pay 99 pounds a month to get the 50 gigabyte. And now she's getting to the top of that. And I'm like, look, you should go up to 299. It's like four times the amount of space. It will be ages until you hit this. She's like, can't I just delete stuff? And I'm like, yeah, but then you've deleted stuff. Like, I don't recommend this. And so I ended up convincing her to do that. But this is just me adding on to this whole thing of like,
All of this is bad, right? Like the way in which Apple does iCloud backup, like every part of it is bad. You should have way more flexibility about the storage that you want, like what you're dealing with. Just to be able to add stuff, that should be easy. Even though maybe it is, unless you're Steven. But today in 2025, starting at five gigabytes for free and then 50 gigabytes and then going up to 200.
The tiers are madness. 5 gigabytes, 50 gigabytes, 200 gigabytes, 2 terabytes, 6 terabytes, 12 terabytes. That's the jumping. It's like, Apple, come on, man. Let's do something different here. Let's start with free at 50 gigabytes and then work out the rest from there. This system is just like, it's so bad. It's so bad.
But that was the only thing that I wanted to add on. I did have the thought, I have a family plan with me, and I had the thought of like, do I want to put my mom on my family plan? And I was just sort of like, this feels like it's going to cause me more problems. And I don't know what problems they are, but I don't want to be responsible for whatever they are. And so I was like, mom just paid two pound a month. And I convinced her to do it, and she's done it. Yeah, I mean, unfortunately, that is the answer, is to pay Apple.
for storage that i mean five gigabytes is ridiculous for free like i had that thought again like when i hit the button which i felt wrong it's like okay i'm gonna hit the button because the person told me to maybe they know something i don't know turns out that wasn't true it's uh it's really ridiculous and the pricing and the spacing is weird like going from two terabytes to six terabytes you can go up to 12 i think um with some steps in between you know if you have everything if the stars align for you
But it feels pretty punitive. And they have done some things I want to give them credit for. If you buy a new phone, you temporarily get into iCloud space to back it up to move to a new phone. But then it goes away. Like, you should get a set amount of storage for a year or two years when you buy a device. And beyond that, the prices should be cheaper and the spacing of the things being a bit more even. Like, you said 50 to 200. 200 gigabytes to 2 terabytes.
It's a 10X jump. Like, what are we doing? Why is there not a 500 gig? Like, I don't, I would not, you know, for all of Apple's price laddering, or there's an iPad at this and an iPad at that and iPhone costs this and $7 more, you get this iPhone. Like, do it with your cloud storage too. So people can just increment up as they need to. And it's really frustrating that it's so convoluted.
And it was really frustrating doing all of this, not only because of the Apple ID and the Apple, excuse me, Apple account stuff. I've been using the wrong term the whole show. So much of this stuff is so buggy, especially on the Mac where I was doing most of this because I was just at my desk. Like you go click like an iCloud thing and a sheet would come up in system settings and there'd be no CSS in it. It was like all like plain text or you want to be able to scroll in the window or you try it on the phone and the phone freezes.
So much of this stuff, why does it take 30 minutes for sharing to take place? And even for me, it was hours later before content started being available. Like so much of this stuff is broken and it's really frustrating when you're trying to get something done in a system that's already confusing and convoluted and again, punitive with their pricing. And then to add on like the buttons just don't work sometimes. It was really, really frustrating. Yeah, I assume it was built on a set of...
Old technology. It's set on really old stuff. With a front end built in SwiftUI. It's a real good combination, really. RoyalRainbow asks, can we get Legacy Steven on the show next week? I'm pretty sure we always have Legacy Steven on the show. I think that's the one we talk to. Maybe. There's a different Steven that's out there in the world.
doing stuff well legacy steven knows everything about mobile me that's true dot mac right and that's the one you bring to the show but like when you're out there buying smoothies and shaking hands with the people that's that's the new steven new and improved steven yeah fresh fresh steven i had i had a smoothie with somebody this morning
That's what I'm saying. I know what you're doing. And I know you're not telling that person about MobileMe. No. You're bringing that to this show. It is funny that, you know, MobileMe's cursedness has followed me all the way into 2025. Was MobileMe, that was the one that was really bad? Yeah. Like it launched really bad and like everything was a disaster? Mm-hmm. Yeah. And then they rebranded it to iCloud, right? Yeah. Rebuilt from the ground up. Or whatever. Not for you. Not for me.
So if you don't know about me, I'll put something in the show notes about it. It's a fun time. Anyways, that's my story. Thank you for listening. Congrats. Thank you. What a story. Yeah. Were you talking to this support person through iMessage? No, it was on the web. See, I had to do a thing recently. I don't remember what it was, but I had to cancel an order or something.
And I was talking through iMessage. Yeah, the retail stuff seems to use iMessage because I had an issue with like, I had an issue with an order where like the credit card got declined and they're like, chat with us. And so I did it and it was over iMessage. But this is, I don't know, like, is it, maybe it's because I was on a Mac. So it was like, oh, let's open a Safari window. But it didn't look like iMessage. It just looked like sort of generic, you know, web chat stuff. I guess that was business chat. Is that what that was called?
Yes, and the icons are squares. Yeah, and it's gray, right? Like the actual messages. More people, more companies should use that. I like being able to have these conversations in iMessage rather than trying to keep some like Safari tab open on my iPhone. So I looked at this for us as like a membership support thing.
Like, oh, you can just text us and we'll fix it. Yeah, but then you're texting Fable all the time. You're texting Kathy. Why would you do that to her? That's a terrible idea. Well, so the back end is not. I looked at it when it first came out. It could be different now. Actually, I would like to know if you first had experience with this from the business side, send us some feedback. I'd love to know how it works today. But when I looked at it the first time, first of all, it was extremely complicated to set up. Now there's probably companies that can do it for you as a service.
But it was on the web on the back end. Like it wasn't coming to a phone. My recollection is that it was like a web dashboard thing. Yeah, surely, surely. But, you know, you can always email us if you have something. Email is fine. I like have a somewhat similar thing right now where, you know, with the new Apple Mail stuff, you can like brand your company. Yeah.
You know, like, so you can, like, be a brand. I have my assistant looking at that for Cortex Brand, and it seems like it is very complicated. Like, she's asking me a lot of questions. I think we did it for Mac Stories. Yeah. I think. Yeah. It's in the process. I think we're waiting for business verification now. But none of this stuff is easy, but I guess it's better to be that than to just, I don't know, have me pretend that I'm Disney or something. You could, I mean, just put it all in your email signature.
You know, with like a picture and like, please consider this email before printing. And a quote. And a quote. Design is not how it looks. Design is how it works. Whoa, I like that one. Same job. You know what device he was talking about when he said that? The cube. Federico, do you have a guess? Okay. It was the iPod. Oh, it was the mouse. The circular mouse? Nope. The blue and white.
power mac g3 it had the door that opened down so you get to all the parts inside and he made a joke about that we have the best access story in the business it's called a door which is a very funny line and he said we believe design it's not just how it looks it's how how it works power mac g3 legacy steven he's here all the time yeah see i told you we definitely we don't need more of that guy we have
We have the perfect amount. We don't need to bring on another Legacy Steven to this show. Okay. I'm going to do the Legacy closing now. Oh, I don't know. People will get mad. No, someone wrote us in. They were mad about the goodbyes being in the wrong order. Yeah, no, I would like to read this piece of feedback. Oh, my God. Okay. I think this feedback is hilarious. Okay. Okay. I take this feedback in the manner in which it, I expect, is written in. It looks like, yes, this comes from Fletcher who says,
I may stop listening to the show if the goodbye isn't in the correct order. The ending is entertaining, but the goodbyes must stay. I like that piece of feedback because, look, I'm with Fletcher. I don't know how to end this show anymore. I love hearing Federico say all.
No, people on the internet take things way too seriously sometimes. Yes, but I don't think that's it. It's a good vibe. I think you are taking it too seriously. I don't believe Fletcher is saying, I believe Fletcher is joking. Maybe Fletcher is being serious and they cannot handle it. No, I'm going to speak over you. I'm not going to go last anymore. Maybe Jim can just re-ranger for us. This is my protest now. Wait, so when we get to the same... I am protesting.
How and what? I don't understand. I am going to say goodbye whenever I feel like it. Okay, but are you going to do the outro? No, I'm doing the outro. Okay. Legacy Steven is. Oh, okay. That's a shame. Hey, y'all. No, more southern. More. Do it more. Do how it really is. Or just go more southern. What I want most is more southern than high voice. I'm going to give you some framing here, right? You prompt me like I'm an LLM. Yeah, this is like a prompt.
You are at Thanksgiving. It is day two of Thanksgiving, and you're surrounded by your cousins who don't appreciate the work that you do. That's true. Your cousins tend to know about the fact that your accent has changed. Consider this as you now give this closing. What you're trying to do is fit in at Thanksgiving around your family whose accents never changed. That's your prompt.
Do I have to fit in like politically? That's up to you. I mean, this outro could get into all. Y'all, we're going to make the closing grade again. We're doing it. I just hit the desk really hard. We'd love to hear y'all's feedback. You want to go connectedfeedback.com.
And if you want to become a member, I can't do it. If you want to become a member. No, you were doing it. It was good. It was good. You're doing it. If you want to become a member and get longer ad-free shows, getconnectedpro.com. It's on the internet. You can find Frederico. There it is. There it is. At maxstories.net. And he is vatici. V-I-T-I.
CCI across social media. He's on the TikTok. Across them socials. All right. You can follow Mike. It's so hard to do. Mike. Mike. Mike. My wife. Mike hosts a bunch of other shows across Relay. You can check out his work. Cortex Brand. It's just hard to do. Brand. This is perfect.
And he's I, Mike, or Mike Hurley. That's forced gun. Stephen, is this cultural appropriation? I live in the South. I'm appropriating my cousins. Do you? Because it doesn't sound like you do. Nor does it sound how I used to sound, I don't think. You can find... I'm done. I'm done with it. You can find my writing... No, come on. Commit. No, commit. Come on. You're so close now.
That's so embarrassing. You can find my writing at 512pixels.net. You just got to slow it down. Yeah, like some molasses. You got molasses in your mouth. And I co-host MPU on Relay. No, no, no. No, you did Relay better before. Relay. It's like relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay. Relay.
iPhone. iPhone. Or your iPad. Just go back far enough. We're not making fun of people. We're making fun of Steven. Yeah. If you want to hear, just go back. It's all on the website. Go relay.fm slash prompt. Just hit one of those and you'll hear it. Federico, if Italians listened to you, would they hear a difference? Oh, what do you mean? Because when I listen to me from then, I can hear how I have become more American.
Oh, no, no, no, no, no. I have a very thick Roman accent. But no, but like if people... Ah, okay. Yeah, but I guess probably what would be the case is if I listened to you then, I would hear a different English...
You've probably done what I've done. I bet you spoke English then in a more Italian way than you do now. That's what I'm looking for. My Italian hasn't changed. Okay, but your English definitely has. Well, that's the hope. Okay, I'd like to thank Ecamm for sponsoring the show this week. Thank you, members. Ecamm. Can't mess. I can't get on to me for that. Learn more about them in the show notes. And until next week, y'all say goodbye. Cheerio. You didn't really do anything except faster.
No, I waited for you because I am not going first. But you didn't speak over me. You just spoke after me, but quickly. It's like you're trying to sneak in a door as it's closing. Bye, y'all.