iCloud is, when you think about it, kind of a thankless service. At its best you don’t notice it—everything, in the unofficial mantra of Apple dating back decades, just works. Your data is in sync across all your devices, changes update immediately, and you never get a single error message.
The thing is, like a lot of Apple tech, it’s a black box. Data goes in, data goes out. What happens in the middle…well, shrug. You just put your faith in the fact that what’s working will keep working.
But as anybody who’s ever tried to troubleshoot iCloud problems can tell you, when it goes wrong, trying to fix it is an exercise in frustration—as I learned recently, in a particularly spectacular fashion.
Intermittently cloudy
This is a bad news error message.
At about 9am Eastern this past Monday, my connection to iCloud went kaput. I first noticed the issue on my MacBook Air: my iCloud mail wasn’t being fetched, messages that I read or deleted were popping up again, and I couldn’t access files in my iCloud Drive.
At first blush, my other devices seemed to be fine, leading me to conclude that there was some specific issue with iCloud on the MacBook. I chalked it up to some weirdness with having reinstalled the final version of Sonoma atop the beta, and started off on the usual troubleshooting steps: quitting apps, restarting, and then the big guns—logging out of iCloud.
That’s the point where things went truly amiss. While I was nominally able to log back into iCloud, most of my data wasn’t actually syncing back. A dialog box told me that I needed to verify my account in order to re-establish end-to-end encryption for sensitive information like my keychain and health data, but clicking the prompted button did…absolutely nothing.
As a very busy September turns over into October, we’ve got an episode packed with follow-up: Tim Cook takes another European vacation, the Vision Pro product roadmap recedes, Apple considers its search-engine strategy, and we review macOS Sonoma.
A new iPhone SE will probably arrive some day, unlike some other potential Apple products I could mention (cough, car and low-cost Vision Pro). Meanwhile Jony Ive is keeping busy hastening the robot apocalypse.
SE what I did there?
If you don’t have the bank for an iPhone 15, let alone an iPhone 15 Pro, don’t fret. A new iPhone SE is on the horizon. Wayyy over there between the land and the sky.
The new SE, which isn’t expected until 2025, will reportedly have the same form factor as the iPhone 14, but will feature an action button and, of course, USB-C connectivity. It would be the first SE with Face ID rather than Touch ID and is reportedly being used to test Apple’s own 5G modem.
Speaking of more consumer-friendly smartphones, Samsung recently leaked details of its new Galaxy S23 FE which, despite what you may think, is not the one with a high-density floppy drive. In this case, the “FE” stands for “Fan Edition”.
No, not because it has a fan in it.
I don’t think.
Lest you think “At least ‘FE’ stands for something. ‘SE’ doesn’t stand for anything!”, not so. Phil Schiller has previously indicated that “SE” stands for “Special Edition”. So there you go. As the codename for Apple’s end-run-around-Qualcomm modem is “Sinope”, let’s just hope “SE” doesn’t stand for “Sinope Explosions”.
Not seeing it
You may one day be able to get a fourth-generation iPhone SE, but it’s looking less likely that two other rumored Apple products will make it to market any time in the near future.
According to Ming-Chi Kuo, “The development of the Apple Car seems to have lost all visibility at the moment.” I’m not an automotive expert but I think losing visibility is definitely not something you want in a car. Kuo says that Apple will have to “adopt an acquisition strategy” if it hopes to ship anything in the foreseeable future. Possibly a good time to make an offer to a narcissist distracted by money-losing vanity projects?
The car’s not the only Apple product Kuo has bad news about. He further believes Apple may have canceled plans to ship a low-cost Vision Pro, which previous rumors suggested could have launched in 2025.
Christmas 2025 is officially ruined.
If you’re feeling disappointed by this news, look at it this way: it’s probably saving you something like $103,000.
As reported by The Information, Ive has been in talks with Altman about building a new AI device. It’s unclear at this point what the purpose of this device will be or what it will look like…
Picture a black rectangle, with a glowing red circle set in it. What could go wrong? As long as you don’t get between it and a power outlet, you should be fine.
…but sources familiar with the conversations say that they want to create a “new hardware for the age of AI.”
Ive is, of course, legendary for his beautiful designs. But the latter part of his tenure at Apple—marked by iOS 7, butterfly keyboards and a “NO MORE PORTS OF ANY KIND” mentality—would indicate he was somewhat less focused on usability. That could be a perfect match for a device that has a mind of its own.
I’ve always said that if you’re going to make a humanity-killing artificial intelligence then it should at least come in a pretty box.
[John Moltz is a Six Colors contributor. You can find him on Mastodon at Mastodon.social/@moltz and he sells items with references you might get on Cotton Bureau.]
And thus was Tim Cook finally brought low—not by Apple’s anti-union practices, nor by his continued willingness to do business with a charming individual like Elon Musk, nor even by Apple’s questionable relationships with the Chinese government.
But by an iPhone case.
The tapestry of Cook’s descent is woven finely, with threads coalescing from across his tenure. As the history books tell us, the beginning of the end for Tim Cook’s regime at Apple, those many years ago, was precipitated by what seemed the most reasonable of initiatives: replacing leather goods with a more environmentally sustainable material. After all, who ever got in trouble for not slaughtering a sacred cow?
The problem, however, lay in the new material. An attempt to ape the feel of premium suede, it proved vulnerable to scratches, easily stained, and less durable than the animal-based material it had supplanted.
All of that would have been bad enough, but the subsequent revelation that the so-called fabric was nothing more than cut-up patches of Eddy Cue’s suits shook the Apple community to its very core.
Cook was barraged with emails, day and night, from irate customers across the world insisting that he return the fine Corinthian leather to its rightful place among Apple cases and watchbands. Attempts to placate them, to explain the environmental impact of animal products, fell on deaf ears, even after two further sketches starring Octavia Spencer followed by a thirteen-episode miniseries on Apple TV+, One Tough Mother Nature. The merest mention of the case’s material—soon banned from utterance in Apple Park’s halls—evinced the most Tim Apple of reactions.
The only refuge for the CEO was the barren moonscape afforded to him by his nightly forays with the Vision Pro. So complete was his solitude, that Cook surprised everyone when he opted to have the company’s future development in the product line halted, so that he would not be disturbed in his “lunar sanctuary.”
Soon he took to spending more and more time there, donning the spatial computer in meetings while his deputies looked on in dismay and attempted to cover for him. “Tim is just very personally invested in the future of AR,” Craig Federighi assured befuddled project leads, even as they found themselves pinned by the dead-eyed stare of Cook’s simulated gaze.
Even Apple’s storied PR handlers couldn’t spin this debacle forever. It wasn’t long before discontented murmurs of replacement began to crescendo amongst the rank and file. But even before any action could be taken, Cook simply…vanished. One morning, at 4:30am, his assistant entered his office to find it vacant but for a set of chic eyeglasses, neatly folded on the desk.
What became of Cook is still unknown to this day, but there are those who say that if you stroll amongst Apple Park’s orchard in the dead of night and listen carefully, you can still hear an anguished voice crying “FineWooooovennnnnnn.”
[Dan Moren is the East Coast Bureau Chief of Six Colors, as well as an author, podcaster, and two-time Jeopardy! champion. You can find him on Mastodon at @dmoren@zeppelin.flights or reach him by email at dan@sixcolors.com. His next novel, the sci-fi adventure Eternity's Tomb, will be released in November 2026.]
My thanks to Kolide for sponsoring Six Colors this week.
Getting OS updates installed on end user devices should be easy, but of course it isn’t. Forcing restarts without user approval will lead to data loss (and angry users), but most users don’t install updates themselves!
OS updates are the single most common issue Kolide’s customers want them to
solve. Kolide reaches out to users directly with instructions on how to get their devices into compliance. The user chooses when to restart, but if they don’t fix the problem by a predetermined deadline, they’re unable to authenticate with Okta.
Apple updated almost every system app in watchOS 10. Unfortunately, the redesign of the Timer app is a serious regression, according to Iconfactory developer Craig Hockenberry:
The new visual appearance and functionality of watchOS 10 is a welcome change. There was clearly a lot of design and engineering effort put into this new interface and the improvements are tangible for most apps.
Unfortunately, the app that I use the most on the Apple Watch has lost much of its usability, both in functionality and accessibility.
Using plenty of examples and use cases, Hockenberry masterfully chronicles all the ways the new app fails him and, presumably, many other users. The details matter.
So it sounds like a lot of people don’t like Apple’s new FineWoven material, which is used in the company’s new iPhone 15 cases instead of leather.
FineWoven has variously been described as plasticy, tacky (usually in the materials/stickiness sense), and cheap feeling. I received a (mulberry) FineWoven case this week and clapped it onto an iPhone 15 Pro. No one should be more surprised than me to find that… get ready…
I didn’t hate it.
At first.
In my brain, I’m a lovable contrarian, always happy to talk about price and accessibility when the rest of the world is going all wobbly for a new camera system, titanium or ProMotion. I relish the space I inhabit. But I did not expect to have an opinion, contrarian or otherwise, about FineWoven.
Here is where I confess that I care about cases. My phone has two; a leather wallet case from Tucah and the Smartish Gripmunk for when I’m at home.
That’s right. I switch when I get home, just like Mr. Rogers and his sweater. Judge me if you must.
But I don’t usually buy Apple cases, because there’s no full-on wallet style, and the price for the bumper styles is too high for my taste—FineWoven definitely included. My two third-party cases equal the approximate cost of one FineWoven.
And so, when an iPhone 15 Pro accompanied by a FineWoven case came skidding into my life this week, I opened the case package first. Because drama!
Don’t expect FineWoven to feel or look like leather. It does not. But putting the case on my phone did not result in instant outrage or palpitations. It was, like the name says, fine. The sides feel good to hold—smooth, but not too slippery.
The back is a bit of another story. Dragging my nails across the material yielded a sort of rhythmic squeakiness that I suppose I meant to be reminiscent of suede. (The case did not become scratched when I did this.) This surface does seem like a potential dirt magnet, but in the day I’ve been carrying it around, the dirt seems to have remained at bay. I have not dropped it from great heights, or given it to a family pet to gnaw. My first impression of FineWoven durability, except the part that’s colored by some of the most scorching product reviews I’ve ever read, has been: It’s fine.
Some users have reported problems with the connector cutouts at the bottom of the new cases. Sure enough, the first non-Apple USB-C cable I plugged into the phone fell right out. When I took the case off, everything was great again, just as it had been with a new Apple cable that shipped with the iPhone 15 Pro. Whatever my take on the aesthetics of the case, a bad connector cutout is a stone-cold deal breaker, even though I also have a couple of MagSafe pucks in service.
My advice to any who resisted the pull of first-day ordering, and might want to go FineWoven, is to view and touch them in person before you buy one. Look at the (surely well handled) ones in an Apple Store. Roll one around on your palm. And by all means, watch the YouTube videos where people torture a $60 case, rather than the phone it’s meant to protect.
And even if you like the case, consider waiting a few weeks or months for a new supply with better connector cutouts. Fortunately, there are a lot of less expensive cases out there, though they may not provide FineWoven’s eco bonafides, and certainly don’t have the branded appeal of an Apple logo.
One of the biggest imprints Steve Jobs and Jony Ive left on Apple’s design process is a certain kind of product idealism. At its best, Apple is striving to take ridiculously complex products, fusions of cutting-edge computer hardware design and eye-wateringly enormous software code bases, and make them simple.
It’s a philosophy that has led Apple to build wildly successful products that its customers love. And there’s one new iPhone 15 feature that perfectly illustrates why Apple’s idealism can take it to very interesting places.
Our favorite (or least-favorite) features in macOS Sonoma, our harrowing AppleCare stories, the cases we do or don’t have on our phones, and whether we upgraded to an iPhone 15.
macOS Sonoma is an update that feels small--but in all the best ways. Upgrading it won't change how you look at your Mac, at least not at first. This means that if you're desperate for change to longstanding features of macOS, you will not find what you're looking for in macOS Sonoma. I suspect, however, that most Mac users just want incremental improvements without disruptive changes. Slow and steady wins the race.
To be sure, Apple is tinkering quite a bit around the edges, but mostly in the sense of minor features getting a facelift or new quality-of-life features that span across its platforms. If all the effort expended getting visionOS ready to ship has meant that things are quieter than usual around these parts, so be it. macOS Sonoma will make portions of your Mac experience better (with some really nice detail work on Apple's part!) without breaking the stuff you count on. That's my kind of update.
Free the widgets
iOS 14 introduced a new form of attractive informational widget to the iPhone, and iOS 15 extended it to the iPad. macOS Big Sur introduced widgets to the Mac, but in the least visible way, trapped in the Notification Center sidebar.
With Sonoma (and iOS and iPadOS), widgets can now be interactive, but more importantly for the Mac, they can now go where no Apple widget--not even Dashboard widgets, back in the day1--has gone before. In macOS Sonoma, widgets can live in Notification Center or on the Desktop.
Widgets live on the Desktop, stuck to it like a bunch of stickers, rather than floating in some sort of weird interstitial layer. As a result, Widgets can never float above your windows. If your windows are covering up the Desktop, the only way to see widgets is to move, close, or hide those windows. (I've been giving the Reveal Desktop command--accessible via function key or by spreading your fingers out on a trackpad--a real workout.) To make it a little easier, Apple has also imported a convention from Stage Manager, in which clicking on the Desktop hides everything but the Desktop. It makes sense, I suppose, but I hate it--my years of bringing Finder forward by clicking on the Desktop make it a nonstarter--and thankfully, Apple has given users the option to turn that gesture off when they're not in Stage Manager.
The "stuck to the Desktop" approach is simple, and I think that's why Apple chose it, but I'm a little disappointed that there's no way to float a widget or the entire widget layer above Mac windows, even temporarily. If you want to work with a widget (they're interactive now, after all) while looking at content in a standard window, you'll need to rearrange or hide windows, which is probably more work than it's worth.
Widgets can dynamically shift between color and monochrome--or you can choose to keep them in either style all the time.
Apple has also chosen by default to have widgets become desaturated of color--and therefore be a bit less obnoxious--when the Desktop/Finder isn't selected. It definitely reduces the distraction, though widgets are also a lot less pretty when they're desaturated. Fortunately, if you don't mind the distraction, you can set widgets to display in full color all of the time. I chose this setting and got used to color widgets pretty quickly. (If you prefer the monochromatic look, you can also choose for widgets to remain monochromatic all the time.)
You can even choose settings for iPhone widgets.
Of course, one of the other big limitations of widgets on macOS has been that they require a corresponding macOS app--and some iPhone and iPad apps with cool widgets never make their way to macOS. To counteract this problem, Apple has added a feature that lets iPhone widgets run on the Mac. If your iPhone is on the same network as your Mac or within AirDrop distance, its apps will be available on the Mac. (They obviously won't work if the iPhone leaves the house.)
It's a pretty cool idea, and when it works, it feels like magic. I added a widget I built for my iPhone using Simon Støvring's Scriptable app, which isn't available on the Mac, and it worked, miraculously.
Unfortunately, iOS 17's entire widget architecture feels a little bit shaky right now. Occasionally, widgets just stop updating or go completely blank, especially if there's been an update in the App Store (or, for beta users, via TestFlight). I've restarted my iPhone more in the last few months than I had in the previous few years, all because it was the only way to get my widgets to start updating again. And when an iPhone widget turned into a zombie on iOS, it vanished entirely from my Mac's Desktop. It's frustrating, and Apple needs to get this issue fixed.
Apple provides widget guides, but you can put them anywhere you want.
I'm impressed with the work Apple has put into how you arrange widgets on the Desktop. It's essentially free-form; you can put widgets anywhere. But when the widget you're dragging gets close to other widgets, it will snap into alignment with those widgets.
At first, I thought the entire Desktop was a grid, but that's not what's happening--Apple's just making it easy for adjacent widgets to look properly aligned. (Items that live on the Desktop can't be lost under widgets, either--as you drag a widget around, all the other items on your Desktop get out of the way.)
These touches say a lot about Apple's priorities. The company wants widgets on the Mac desktop to not look messy, and it's done a lot of extra work to make that so.
While it's nice to have widgets on the Mac, the fact is that they're imports from iOS and iPadOS and, as a result, don't quite fit right. All widgets feel a bit too large, especially if you're trying to use them on a laptop display--the appropriate scale for iOS just seems a bit wrong for macOS.
Then there's the entire concept of the "interactive widget," which is a real winner on iOS 17 but mostly a nonsequitur on macOS. Yes, your to-do list app now comes with a widget that displays items you can check off... but on the Mac, why not just have your to-do app open to do that task? The Mac is such an able multitasker, and its multi-window interface is so powerful that this feature is blunted quite a bit. This is not to say that there aren't use cases for interactive widgets on the Mac... it's just that they're a lot less exciting.
Widgets are great when it comes to glanceability. It's nice to lay that weather widget on my Desktop and know that I can just peek over in the corner of my screen to see the current temperature and forecast. But even here, the Mac's flexibility blunts the value somewhat: most Macs are laptops, and laptops have limited screen space. Is a big widget from iOS sitting on your Desktop (and requiring window management to reveal it) a better glanceable experience than putting items in the Mac's original glanceable space, the menu bar? Sometimes, the answer will be yes, but it all feels less necessary than on iOS.
There was a bug that let you move Dashboard widgets out of the Dashboard layer and into your regular interface, but it was temporary and unsupported. ↩
Live from Memphis in the aftermath of the Relay FM Podcastathon, Myke and Jason take delivery of new iPhones and Apple Watches. Also, General Motors continues its drive for Apple-like services revenue.
Apple won’t let you gamble on the iPhone, but it seriously considered letting you do the next worst thing. The iPhone 15 Pro Max seems to be selling well but that FineWoven case… eesh.
Taking stock
You loved Apple Cash, you raved about the Apple Card and you adore the Apple Savings Account. But how would you have felt about Apple Stock Trading?
One ability apparently pitched by executives was the ability to invest in Apple shares using spare cash.
Trader, can you spare a dime?
Was this just an elaborate scheme to get people to actually use the Stocks app? Alas, we may never know as this plan was shelved.
When markets worsened last year, Apple and Goldman Sachs shelved the project due to fears over backlash if users lost money in the stock market, and refocused attention on a high-interest savings account for Apple Card users.
Shocking breaking news: sometimes people lose money on the stock market. More on this as information unfolds.
You know, uh, we had a whole Great Depression over that, as I recall. It’s probably a good thing Apple’s plan has been mothballed. You’re not going to have any money to invest after buying an iPhone 15 Pro Max anyway.
Trickle down cameranomics
What an age we live in that we can know how well the iPhone 15 Pro is selling before anyone even gets one. Can you believe we used to have to wait sometimes months to hear how well a particular device was selling? Progress is really amazing.
But it seems the iPhone 15 Pro Max is selling quite well. The economy, it turns out, runs on cameras. Who knew?
Well, Apple knew, apparently. And no one blinked at the fact that you couldn’t get the iPhone 15 Pro Max with 128 GB of storage. I mean, if you’re buying a $1200 smartphone, you’re probably going to want the extra storage anyway. Also, Apple puts the Pro line first on its iPhone web page, so probably a lot of people are just clicking the first thing they see and plopping down $1200, thinking that’s just what iPhones cost these days.
The Verge’s first look at FineWoven doesn’t go so far as to say “Please go back to killing cows” but it definitely lets you know FineWoven is no leather. It does call several cows “real jerks”, though.
OK, not really, but that would have been funny if they had.
Apparently FineWoven cases are more prone to scratches than leather, and here we had all thought we lived in a post-scratch society. It’s a real disappointment. Given that Apple charges a fair amount for these cases, you might want to consider other options if you’re a case person. It will still protect the phone and isn’t that the real point of a case? To take the damage you don’t want the phone to get? You don’t want scratches on the phone, you don’t want scratches on the case, what do you want scratches on?
Let us consider that maybe FineWoven is like early attempts to replace the hamburger. If you were looking for a hamburger in the ‘80s, you were definitely going to be disappointed by a Gardenburger. It took years to create more passable alternatives, like the Beyond Burger and the Impossible Burger and just eating a regular hamburger and then buying some carbon offsets.
Sorry, I wasn’t supposed to type that last one out loud.
Hopefully Apple is able to keep improving the material, because despite what The Verge didn’t actually say, most cows are good people.
[John Moltz is a Six Colors contributor. You can find him on Mastodon at Mastodon.social/@moltz and he sells items with references you might get on Cotton Bureau.]
As I write this I’m sitting at St. Jude, about three hours into our 12-hour podcast telethon in support of St. Jude’s goal of stopping childhood cancer. I’m one of four hosts along with Stephen Hackett, Myke Hurley, and Kathy Campbell.
My thanks to BZG Apps, maker of Unite 5, for sponsoring Six Colors this week.
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