We’ll all know soon enough, but kudos to Bloomberg’s Mark Gurman for breaking some new details 12 hours before Apple’s event begins:

Its device, called the iPhone Duo, will start at $2,000… The entry-level version will include 256 gigabytes of storage, with Apple offering higher-capacity versions that will take the price all the way up to roughly $3,000…. There will be a magnetic hinge system and support for the Apple Pencil stylus.

The Duo will go on sale as early as October and come in white and dark blue.

iPhone Duo is a good name. Not only does it make sense — two screens! — but it references an old Apple product name, and keeps iPhone Ultra in reserve for future use.

I’ve been wondering about Apple Pencil support on the iPhone for some time now. This product does sort of make sense for it, given the larger canvas of an interior screen.

The starting price seems high in practical terms, but also actually quite aggressive given the current out-of-control state of affairs for tech gadget costs. (Obviously the better configurations will escalate rapidly in price, as is Apple’s tradition.)

Gurman also suggests this device won’t ship as quickly as the new iPhone Pro models—again, not too much of a surprise, as that’s what happened with the iPhone X. And as for the colors, well, dark blue is certainly more interesting than another Space Gray. I do wonder why the Color Czar has decided that black is out as a color, but fashion does what it wants.

Anyway, happy Christmas Eve (and Christmas morning) everyone. See you back here after all is revealed.

Go to the linked site.

Read on Six Colors.

You might be interested in knowing how to embrace Apple Passwords with a bear hug, leaving behind your current password manager. If you tried Apple’s Passwords app in the past and were disappointed, you should probably give it another try. The improvements Apple has made in the last couple of releases have brought it to what I consider parity with the most important useful features of well-designed third-party password managers.

Despite that, Passwords is focused on—no surprise—passwords and password-like items: website logins, passkeys, and Time-based One-Time Passwords (TOTPs). Many password managers include a junk drawer of other kinds of structured material you can store that doesn’t map directly to Apple’s Passwords structure. If you’re mostly using a third-party system for password-esque stuff and use all Apple devices or Apple and a Windows PC, a migration is straightforward. Otherwise, it can be hairier and could involve rethinking how you store assorted data.

You can use iCloud Passwords with Windows (and then use Microsoft Edge, Firefox, or Google Chrome). You can also use browsers other than Safari on a Mac with an iCloud Passwords plug-in or extension. However, if you or people you currently shared information with use Android, Linux/Unix, or ChromeOS, this migration won’t work for you: those platforms aren’t supported, and there’s no web app for iCloud Passwords.

Because Joe Kissell and I have written entire books that help with different components involved in a password manager migration, I’ll include references throughout to appropriate Take Control series books. For a general grounding in passwords, for example, I recommend reading Joe Kissell’s Take Control of Your Passwords, updated earlier this year.

Map the data connections

As I noted, Passwords is best at passwords (and passkeys and TOTPs), and filling them in on webpages and in apps. If you care mostly about this, you’re in luck, as you can easily migrate data of these kinds:

• Website and app logins: Account logins move to Passwords.
• Loose passwords: Ones that have no direct connection to an app or site, like a bank card PIN, also move to Passwords.
• TOTPs: These confirmation codes can be migrated. However, there’s a technical detail with how they may be stored by third parties (or Apple) that can prevent the migration and might require using a backup code; see details below.
• Passkeys: The password “industry” finally developed and rolled out a secure copying system that Apple supports that will let you move passkeys among password managers. This requires migrating on an iPhone or iPad; you can’t move these on a Mac.

Two other categories of fill-in entries that aren’t managed in Passwords can be handled—and you may already be using—in Wallet and Safari:

• Payment cards: Payment cards need to move to Wallet & Apple Pay. You have to enter these manually as AutoFill Cards, unless you’ve already done so or added the card to Apple Pay. It’s a little complicated, as I explain.
• Identities: Apple supports filling in personal or business address information through Safari using AutoFill.

(You can see Safari’s evolution on the Mac at Safari: Settings: AutoFill: your personal contact now links to Contacts, user name and passwords to Passwords, and credit cards to Wallet & Apple Pay.)

Where you will be left hanging by Apple:

• Miscellaneous secure items and attachments: If you store Social Security numbers and other account information that is distinct from a password, but you want to have available to fill in at particular websites or by searching Passwords, you can create these as entries in Passwords. In some cases, you may want to create entries in Notes (with additional security, described later).
• Structured data: You may have bank accounts, passports, driver licenses, memberships, software licenses, or other structured information stored in a password manager. That is a trickier needle to thread, as Passwords offers no support beyond a Note field.

For both of these, you might want to migrate to… a password manager. But wait! This would be one you use solely for secure storage of these miscellaneous structured or less-classifiable items, not for field-oriented secrets and accounts you want to fill in.

There’s one more important migration issue:

• Shared vaults and items: If you use a password manager that supports secure storage areas with other people—like vaults in 1Password, Dashlane, or LastPass, for example—Passwords provides something akin, though not precisely the same: Shared Groups. Because of the above provisos, many non-password items shared via a third-party manager will need to be migrated to Notes or another secured shared item-storage-based space.

Three big things that may derail the whole migration for you:

• Tags/labels: Some people make use of metadata organizational systems, like tags. These don’t transfer to Passwords at all!
• Extra data: Much like the paper card catalogs of yore had book information plus tons of annotation, accumulated over time, you may have used password manager features to add extensive notes, additional fields, include attachments, and create richly detailed records. All that will be gone, like tears in rain. True, Passwords has a Notes field, but it lacks structure, rich text, and Markdown support. If you move to another, more focused password manager, you may be able to retain this.
• Access after you’re gone: Non-Apple password managers have recovery kits that could allow a relative or other party who has that information to gain access to stored, synced data. Apple’s Legacy Contacts system, which allows an executor or other authorized person to access your data when you’re gone, excludes iCloud Keychain: no passwords, passkeys, Wi-Fi passwords, or other data. However, Legacy Contacts must be activated; until it is, it’s possible for someone who retains access to one or more of your devices to view your passwords and other data in Passwords. (See Joe Kissell’s Take Control of Your Digital Legacy, or my Take Control of Your Apple Account.

One last bit of aggravation? Passwords does not yet support removing duplicates!

Plan your migration

As you consider migrating, I urge you to run your old manager and Passwords in parallel.¹ Particularly if you store a lot of different kinds of data in your old manager, you may want to be able to consult it and migrate some of it over time. This can be a pain if you are paying an annual fee and the renewal is coming up soon. Consult the maker’s website to see whether you retain access to your data after a subscription expires and, if that bothers you, in what form.

The place to start is pruning old entries.

First, sort by last modified date. Did I know that nearly 2,200 of my 2,600 entries haven’t been modified since 2022? Some since 2008? I did not. However, you likely don’t want to delete these wholesale, because there may be secrets you can’t recover. Online backup private keys (such as with Backblaze), Bitcoin and other cryptocurrency phrases or keys, or other secrets you set once need to be retained or you lose access forever.

My strategy:

• First, export everything. These exports are unencrypted and must be performed on your Mac. The export won’t include passkeys. (See below for that pathway.) This gives you a revert point. Because there are so many export formats across systems, I refer you to the software documentation to pick the best one. Warning: That file will be unencrypted and is like plutonium. Handle with care. The best plan is to use Disk Utility to create a disk image (APFS, 256-bit AES, Sparse Bundle Image), use a password you know or that is stored in Passwords, and then export directly to that encrypted image. The reason? If you save the file elsewhere, it might be backed up to Time Machine or become accessible in a way you didn’t intend. When unmounted, the drive is as secure as your startup volume. Just don’t forget or lose the password!

• Move all the older entries into a group. You might be able to create a group, tag all entries, or, in the worst case, move to a separate vault. In 1Password, the only strategy I found was to create a new vault called Outdated Entries and move all the older entries there. Warning: When selecting, make sure you aren’t including entries from all vaults, as that might move items you share with others or that others share with you.

• Next, sort by name or title. This lets you scan through entries and identify duplicates. I found a number of items I’d already labeled “outdated,” or that were from services I couldn’t even remember. However, there were also a huge number of passwords and account logins that hadn’t been changed in more than four years—some for more than a decade! (There’s no reason to change uniquely set passwords routinely unless your current one is weak and a site is compromised. Most password managers, including Passwords, let you know about weak and reused passwords.) This process can be mighty tedious, which is why I’d recommend tackling it over time rather than all at once.

When you’re pruned, cleaned up, and otherwise reduced, you can now use the set you’re exporting; it’s time to go to the next step.

Export your secrets

Your best and first choice should be to use your iPhone or iPad; at this time, you can only perform a secure password storage transfer in iOS.² Major password managers support this transfer method, which lets you move passkeys—it’s currently the only way to migrate a passkey.³

Here’s how it appears and works in 1Password:⁴

1. Navigate to the export section of 1Password—that’s Lock (upper-left corner): Settings: Advanced: Start Export.
2. Enter your account name; the app provides a hint. Tap “Approve export.”
3. An explanation screen appears. Tap Continue.
4. Choose the destination. In this case, tap Passwords, then tap Continue.
5. Tap Continue in “Passwords,” and you’re switched to the Passwords app, where you can watch the import in progress.

While this is the best method, you can also export from most apps in CSV (comma-separated values) format, which truncates most information and likely leads to problems. Warning: You will have to re-create your passkeys. You may need to use the desktop version of the password manager to export. In Passwords for Mac, choose File: Import Passwords from File, click Choose File, select the file, and proceed. This doesn’t overwrite entries.

Now, check important accounts:

• Does the regular login work? If not, reset the password. Take this opportunity to upgrade to TOTP or a passkey if either is available.
• Does TOTP or a passkey work for logging in? If not, find a backup code or another method to generate a new TOTP or passkey.

TOTPs have a particular idiosyncrasy. They are seeded with a secret generated by a website. The site displays that code as a QR code, so you rarely need to copy it, though Password and other managers allow you to do so. When migrating an entry with a TOTP, it might appear in its URL format, which is generically like otpauth://totp/user@user.user?secret=SEQUENCE in the Notes field instead of appearing as a TOTP within Passwords. If that’s the case, you can fix it manually:

1. Copy the text after secret=.
2. Tap or click Edit.
3. Tap or click Set Up Code.
4. Paste the secret you copied into the Setup Key field.
5. Tap or click Use Setup Key.
6. Tap or click Done.

If that fails, log into the website in question and use a backup code or other means to re-enroll with TOTP.

Enter credit cards, set up AutoFill, and move to Notes

Before getting started, I strongly recommend enabling Advanced Data Protection in iCloud. ADP improves iCloud security by encrypting nearly all application data—iCloud Drive, Messages, Photos, Notes, etc.—via keys stored only on your devices, just like iCloud Keychain. Without ADP, these kinds of data are encrypted in transit and at rest using only Apple’s encryption secrets, and could be demanded via a government subpoena or someone gaining access to your Apple Account. (Note that contacts, events, and email remain encrypted at rest, not end-to-end, because of the need for compatibility with third-party software.)

Follow the steps in the link to enable. You can also still access this information via iCloud.com through a process that enables a temporary end-to-end session. (For more about ADP, see Joe Kissell’s Take Control of iCloud or my recently updated for the 27 releases, Take Control of Securing Your Apple Devices.)

Now, work through these categories:

• Payment cards: Use Settings: Wallet & Apple Pay on an iPhone or iPad, or System Settings: Wallet & Apple Pay on a Mac. Tap or click AutoFill cards and authentication. Now you can tap or click Add Card to provide the card details. This lets you fill in the card anywhere there’s a form field or wherever you can tap or Control-click/right-click in a field and bring up AutoFill as a menu item. AutoFill cards sync across your devices when Wallet sync is active in iCloud (Settings/System Settings: Your Name: iCloud: See All). For more on working with Wallet and payment cards, see my book Take Control of Apple Wallet. This information is secured end-to-end.

• Identity filling: A different kind of AutoFill, for identity information, is found in Settings: Apps: Safari: AutoFill or Safari: Settings: AutoFill. Enable Use Contact Info on an iPhone or iPad, or check “Using information from my contacts” on a Mac. Now you can tap the entry next to My Info on an iPhone or iPad, or click Edit to the right of the checkbox label. This lets you pick an entry—you probably already did—and populate it with all the things you’d want to fill in on a form, including multiple addresses. Safari doesn’t protect identity information with ADP. However, the type of address and other information you would use are likely the least important to protect in what would be a very unlikely break-in to an Apple Account or one of your devices.

• Fill in Notes: As I noted earlier, the structured entry style of third-party password managers doesn’t mesh well with either Passwords or Notes. Passwords has a single Notes field, which may be enough for some entries, but not the more detailed ones I describe. The Notes app is structured around entries, but it’s not well designed for hundreds or thousands, and it lacks inherent field data or structure. Judge what you’re storing in your old password manager to figure out if Notes could work. With ADP enabled, it offers strong security. For migrating structured data intact, read on!

Migrate structured data

If you’re looking to move structured entries, I suggest checking out Strongbox, but not for passwords, passkeys, TOTPs, and the like. Its developer offers a free syncing version (for iPhone, iPad, Mac, and Apple Watch) with everything you need except Touch ID/Face ID unlocking. That requires the Pro flavor at $24.99 per year, which includes several other features.⁵

Strongbox, unlike some managers, allows you to sync via a file under your control or through its secure syncing service, depending on your preference. This lets you keep your, er, digital strongbox under your personal control, if that matters to you. It can import from all major password manager export formats.

In testing, it preserved my 1Password structured data extremely well. This included tags. It also arranged my vaults into what it calls groups, letting me retain a sense of what I was sharing with others.

The one complication is that if you want to use one of the migration processes above to copy your items into Passwords, you have to do one of two things after performing your migration:

• In your old manager, delete all passwords, passkeys, and TOTPs. This is dangerous in my accounting, as it reduces your ability to have a parallel working solution, and you could accidentally delete secrets you need to keep.
• Import everything into Strongbox, then select all the passwords, passkeys, and TOTPs from Strongbox, and empty the trash. This gives you two copies of everything: Passwords and old password manager for secrets; Strongbox and old password manager for structured data.

When you’re ready to abandon your old password manager, maybe weeks or months from the migration, you can retain a securely stored backup copy or perhaps retain access depending on the product, while not using it actively or paying renewal fees.

Working in groups

Sharing your passwords and other secrets with other people remains Passwords’ weakest aspect, because Apple offers only Shared Groups. Each entry can be stored only in your personal Passwords storage or in Shared Groups. Otherwise, you have to duplicate an entry, which can cause such entries to drift out of sync.

In the Passwords app, select any entry, then click or tap the Group pop-up menu. You can then choose an existing group or create a new one. When you make your choice, the password, passkey, or other item is now exclusively found in the Shared Groups section, not copied! Passwords doesn’t offer a copy or duplicate feature, so you have to re-create the entry if you want to share it with two or more groups that aren’t a complete overlap of the same people.

It may be easier to understand from a family perspective. Let’s say you have items you share only with your spouse, others with your children, and some with both. You can’t create a “spouse” group and a “children” group. You need to have one for your spouse, one for your children, and one for the whole family. This is where there’s real room for improvement by Apple.

The password rhymes with orange

I know this is a whole rigmarole, but I’m actually impressed that it’s finally doable in a reasonable manner. A couple of years ago, it was not. It was possible a year ago, but I wouldn’t have recommended it. Now, if you’re careful with each step, maintain a backup, and keep your old manager running in parallel as you complete the migration, you should be able to achieve success.

This article was updated on Sept. 10th to add missing details about fixing a broken TOTP import.

[Got a question for the column? You can email glenn@sixcolors.com or use /glenn in our subscriber-only Discord community.]

General Motors has been saying for a few years now that it’s going to get rid of CarPlay and Android Auto on its EVs because, well, reasons.

Well, well, well… maybe not. Ian Wright of CarBuzz writes:

The Cadillac configurator is up for several 2027 models, and we spotted that the Lyriq still shows CarPlay and Android Auto being standard. The Lyriq is Cadillac’s first all-electric vehicle and a tech-forward vehicle that we think is becoming one of the best luxury EVs available. So, it piqued our interest that the GM brand was still including the things it was supposed to be phasing out, and we reached out to Cadillac for comment.

“Cadillac is continuing to evolve its infotainment strategy across the EV portfolio, based on customer feedback, while also prioritizing the native, in-vehicle experience,” a Cadillac representative told CarBuzz. And, the language is telling. The plan was to start the phasing out of phone projection with the 2024 Chevrolet Blazer EV, with CEO Mary Barra saying: “We made a decision to prioritize our EV vehicles during this timeframe, and as we go forward, we’ll continue across the portfolio.”

Wright does a good job at spotting the weasel words in the new Cadillac statement. Three years after a bold pronouncement that GM wasn’t interested in listening to its customers and giving them what they wanted, here comes an “evolve[d] infotainment strategy… based on customer feedback.”

Translation: Oh, people actually do want CarPlay, so we probably should let them have it, or they’re not going to want to buy our cars.

This isn’t how this story needed to go, but if GM wants to silently walk back its stupid pronouncement from 2023, it’s still a win for anyone in the market for a new car.

Go to the linked site.

Read on Six Colors.

A possible replacement for Mac OS arrives in the form of a company founded by a charismatic former Apple executive—but not the one you’re thinking of.

Go to the podcast page.

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The deed is done! John Ternus is now CEO of Apple!

Memomento mori

[extreme TV infomercial announcer voice] Do you suffer from insomnia, sleeplessness, or the condition known as “Snooze Deficiency Syndrome”? Do you lie awake staring at the ceiling, unable to lull yourself to unconsciousness, despite lately really preferring it to consciousness? Well, don’t worry! Apple’s outgoing CEO has you covered!

“Read Tim Cook’s full memo to Apple employees on his last day as CEO”

Today is my last day as CEO of Apple.

Story checks out so far.

This is a moment I always knew would come one day…

BREAKING: FORMER APPLE CEO HAD FIRM GRASP OF THE LINEAR NATURE OF TIME.

…and yet it is still hard to believe it has arrived and I am writing these words.

[sound of 170,000 Apple employees closing an email and going back to whatever it was they were doing before]

If you’re not asleep yet, don’t worry. It goes on like that for kinda a while without saying much of anything. Again, though, if you’re not asleep by the end, don’t worry. Because Apple’s incoming CEO also has you covered.

“Read John Ternus’s full memo to Apple employees on his first day as CEO”

Hang on, I gotta get a cup of coffee before we read this because I’m already pretty groggy.

OK, here we go.

I’m honored to be stepping into this role at what is truly the greatest company in the world…

The greatest company in the world, the greatest network in the world, the greatest phone in the world…

Man, after reading these I feel like I really owe Stan Sigman an apology. Too late for that, I guess.

Ternus’s memo at least has the benefit of being less than half the length of Cook’s, sort of like taking 2 mg of melatonin and then, when it’s not quite working, taking another 1 mg to finally shove you off the cliff and into Morpheus’s welcoming embrace.

Ask your doctor if reading Apple CEO memos is right for you.

Et tu, Phil?

Tim Cook and John Ternus weren’t the only Apple executives updating LinkedIn this week. (“You have been endorsed for ‘Pablum’.”)

“Phil Schiller steps down from leading the App Store and Apple events”

So, developers, please make sure to update your email templates for where to send your angry missives about long App Store review times.

Despite the change:

…Schiller will remain an Apple Fellow and work on “unspecified initiatives.”

“Unspecified initiatives”?! Is that what the kids are calling it these days?

Meanwhile, while his name may still be Luca, he no longer works on the second floor. Or whatever floor he used to work on.

“Ex-Apple CFO Luca Maestri Winding Down His Time at the Company”

After years of counting Apple’s money, Maestri is reportedly looking forward to spending more time with his family money.

With these transitions, don’t be surprised if John Ternus shows up at your door saying “I’m putting a team together! We’re looking for someone with your particular skillset. Are you in?!”

I mean, it’s probably not gonna happen, but it might.

The price may or may not be right

Big week next week as… well, you know what’s gonna happen.

Sometimes I don’t know why we go through this charade of me pretending to present these things as “news” when you probably already know them. It’s ridiculous. I mean, what is even the point of anything?!

Sorry.

Anyway, if you’re wondering how much change you have to find in your couch and the couches of everyone else in your cul-de-sac and every cul-de-sac in the nation in order to get a foldable iPhone, the Apple rumor mill has got you, fam.

“iPhone Ultra’s Very High Price and Features Revealed in New Report”

Awesome! OK! Lay it on us! Here we go! Give us those dirty deets!

TrendForce estimated that the foldable iPhone will have a starting price of $2,099 to $2,299…

Oh, c’mon! I could have done that! That’s like saying “It will be dollars, unless you’re in a country that uses a different currency.”

I’m going to go ahead and predict that it’s going to be on the high end of that for sure and possibly higher, as Samsung’s most recent foldable starts at $1,999 and this is Apple we’re talking about—and not only that but Apple in an era of unprecedentedly high prices for technology (thanks, AI!).

Thus, my couches will remain un-raided as I will not be buying this device. My child’s inheritance is secure.

Our thoughts on the Dyson CameraJet toothbrush, features or products we’d like to see return in the Ternus era, travel devices we brought but never used, and whether we’ve encountered AI-generated food menus.

Go to the podcast page.

It’s the year of Lex on the desktop, mobile and everywhere else.

Go to the podcast page.

Apple’s homegrown next-generating operating system fails to launch, leaving the company in dire straits and searching for a lifeline from outside the company.

Go to the podcast page.

A few months ago I added a “Report a Typo” feature to Six Colors. The goal was to give people a simple place to go — sixcolors.com/typo — if they found a mistake on the website. That Google form inserts the information into a Google Sheet, and a script attached to the Google Sheet kicks off a simple automation that sends me a notification in a couple different places.

This works pretty well. I’m using a very simple Google Apps script to fire off a webhook when there’s a new form submission. The webhook is running on Make.com, which we use for a bunch of simple web automations, but that’s an implementation detail. Make.com posts an item in a private Discord channel and also crafts a custom push notification to my phone using Pushover.

However, the moment I turned this feature on, I discovered the problem with asking people to report errors or typos: Some people see any open channel of communication as an open channel for any sort of communication. I immediately started getting more “this is more a comment than a question” items about articles than actual typo submissions. Commentary included personal preferences for writing style, web design, political references (real or imagined), and much more.

I’m going to make an admission: This sort of feedback is maddening. I want to be alerted about mistakes on the site so I can fix them promptly, but I am not interested in receiving push notifications regarding your opinion of the professionalism and appropriateness of my writing style.

Unfortunately, it’s an open form. There’s nothing to be done. Or is there?

This is a challenge that can’t really be solved by looking for a bunch of keywords. You need wholesale sentiment analysis of the entire submission. This is—brace yourself—actually a good use of a large language model.

I solved this problem by using a plug-in within Make.com that lets me get a reply back from a cloud LLM that uses a simple model with an API cost of pennies per use, but you could also just use Shortcuts to build a version of this automation that runs on a Mac (Tahoe or Golden Gate) using Apple’s built-in models. It works just fine in Shortcuts on my Mac, via the Use Model action. (See screenshot above.)

Here’s the prompt I’m currently using:

Your task is binary classification.

Input: a user-submitted comment about an article, claiming to report an error.

Output: one token only: ALLOW or REJECT.

Definition of ALLOW:
A concrete, objective, verifiable issue in the article. This includes:
* factual mistakes
* spelling, grammar, formatting mistakes
* broken or incorrect links
* wrong names, dates, numbers
* technical inaccuracies
* omissions of material consequences of a feature or change (e.g., failing to mention that a feature deletes stored Wi-Fi passwords)

Definition of REJECT:
Anything subjective. This includes:
* political disagreement
* tone or style complaints
* metaphor or comparison preferences
* ‘you should have covered X more’
* speculation about motives
* emotional reactions or rants
* admissions that it’s not actually a mistake

Classification rules:
1. If the comment identifies a specific factual, technical, or materially consequential issue in the article, return ALLOW.
2. If the issue would meaningfully affect reader understanding or use of a product/feature, treat it as an omission and return ALLOW.
3. If the comment is opinion, taste, politics, vibe, personal criticism, or preference, return REJECT.
4. If there is no concrete, verifiable claim about the article being wrong or incomplete, return REJECT.
5. If it’s off-topic or spam, return REJECT.
6. If it’s a short but simple phrase like “there not their” or “r/sheild/shield”, those are nerdier folks reporting typos and that’s fine, ALLOW.

Respond with exactly one of these two tokens: ALLOW or REJECT. No explanation.

Submission: [[insert report text here]]

This has worked surprisingly well. And, yes, all messages are logged in the original Google Sheet, so I can occasionally check to monitor the quality of the filtering and make sure that the system isn’t failing to pass on actual mistakes.

Artificial Intelligence takes center stage in a few of the apps enjoying this week’s spotlight — and not the kind of AI that’s going to have you rolling your eyes or organizing a protest march against the nearest data center. No, these are actually useful AI features that take some of the busy work of daily life out of your hands so you can concentrate on other things.

AI or no, we’re always looking for top macOS and iOS apps to feature here. If you’ve got something that fits that description, drop us a line at apps@sixcolors.com with a brief outline of the whats, whys, and wherefores.

Now on to this week’s selection…

Sortio

The folders on my Mac are a mess, but who has the time to make sure that everything is filed away in its proper place? AI does, according to the makers of Sortio, a macOS utility that promises to do the hard work of organization on your behalf.

Sortio taps into AI to look at file names and metadata to help it figure out where to put each file. You can also opt to let the utility read the file, sending a 4KB excerpt to your AI provider of choice for even more detailed sorting. (Sortio also offers an offline mode that uses Ollama or LM Studio to keep its activity on your Mac.) You can further refine sorting by telling Sortio to organize things by file type, project, date, and whether the file is for work or personal use..

I took Sortio for a spin, having it go through the folder of articles I’ve written but haven’t bothered to organize for myself. Sortio was smart enough to take my submissions to Awful Announcing and separate them into their own folder. Not every search is that precise — a separate sorting session had Sortio tagging an offer letter from an old employer named Purch as a financial document — but there are edit buttons to correct mislabeled and misfiled material.

You can try out Sortio for free, which gives you enough of an allowance to sort through a few thousand files to get a flavor for how the app performs. After that, you’ll need to buy a license, with the $14.99/month Pro license suitable for most individual users. There are team and enterprise options as well, and paying for an annual license lowers your monthly rate.

AskPlay

AI isn’t just for organizing your folders; it can also generate a playlist for you based on specific artists, songs or moods you’re hoping to hear. At least, that’s the idea behind AskPlay, an app that lives in your menu bar and lets you type or speak plain-English instructions on the type of music you want to listen to.

You’re going to need a few things besides AskPlay and its $1.99/month subscription to make the app work. For starters, AskPlay works exclusively with Apple Music, so you’ll also need to subscribe to Apple’s streaming service. In addition, you’ll need to provide an API key from an AI provider, with AskPlay supporting OpenAI, Anthropic, and OpenRouter.

Those requirements are likely to limit AskPlay’s appeal to some users, but having tried out the app on my Mac, I am impressed by the results. I told AskPlay I wanted to hear songs written by Stephen Sondheim, and it dutifully produced a playlist not just from cast soundtracks but also numbers by vocalists from their own albums. That said, there were a few misfires — the playlist included a song from Tick, Tick… Boom!, a Jonathan Larson musical that only refers to Sondheim, as well as a rap song that shares a title with something Sondheim wrote. Other requests like “play upbeat songs from the ’80s” proved more successful.

An AskPlay feature I appreciate was the ability to augment playlists. After generating a playlist of Merle Haggard songs, I had the app add Johnny Cash music to the queue. Then I told AskPlay to “add more songs like these,” which brought Waylon Jennings, George Jones, and more to the party.

AskPlay seems built for a very specific kind of user, but if you like thematic playlists and already subscribe to the services that make this app tick, it brings another dimension to your listening experience. In addition to working on the Mac, AskPlay is available for a range of Apple devices including the iPhone, iPad and Vision Pro.

Pocket Screen

I don’t know about you, but my workflow often requires me to jump from one window to another to perform a task — and that can often break up my workflow. I’m thinking of when I’m writing something and need to refer to notes I’ve taken in another application or a PDF I have loaded up in Preview. Jumping between apps takes me out of the flow of writing, not to mention that accurately transcribing what’s in one app to the other can occasionally be a hit-or-miss proposition.

Pocket Screen addresses some of that dilemma by creating a floating window of one app that you can keep in view when you’re working on something else. Think of Pocket Screen as a picture-in-picture feature, but for productivity. You can capture a PDF, webpage, video, chat or other kind of information and keep it close at hand in a resizable window that you can move around your desktop. The app supports up to two simultaneous views, according to its developer.

You can freely use Pocket Screen for 10-minute sessions, but true productivity mavens will likely want to unlock the app for unlimited use. That’s a one-time payment of $9.99 to remove any restrictions.

Filtre

Filtre is a Safari extension for anyone whose browsing on the Mac, iPhone, or iPad takes you to places and topics they’d just as soon not read about.

Enter keywords into Filtre, and the extension blocks articles, posts and comments that include anything you consider verboten. For instance, I typed in variations of the Washington Nationals name into Filtre to avoid being spoiled on the result of a baseball game. When I visited ESPN in Safari on my Mac, all references to the Nationals and their in-progress game had been removed from view. (A pause button accessible from the Filtre Extension in Safari’s toolbar lets you restore any filtered-out content if you prefer.)

Filtre comes from the maker of Noir, a Dark Mode-enabling extension that Six Colors has profiled before, so we’re clearly talking about someone who knows their way around Safari extensions. You can try out Filtre free for a week before the extension’s $1.49/month subscription kicks in.

LogZero

You’ve got lots of ways to track everything from calories to moods on your iPhone. LogZero offers to do it all in one place. More significantly, though, LogZero promises to keep all that logged data for your eyes only, with data never leaving your device and everything stored within the app encrypted.

LogZero is a one-stop app for keeping tabs on food intake, meditation breaks, exercise, to-dos, and medications. You can also chart your mood and weight. If that sounds like a lot to keep track of, you can toggle off the items you’re not interested in logging, and they’ll disappear from the interface.

It’s worth downloading the free iOS app to see if it fits your tracking needs, though a paid subscription gives you access to more analytics features plus personalization controls. A monthly subscription costs $5, while the annual rate is $35.

It’s time for another Apple event draft! But before we predict what Apple will introduce next week, we need to send off the Tim Cook Era and discuss a somewhat surprising announcement of new chips and new Macs!

Go to the podcast page.

Today Tim Cook is stepping down as Apple CEO and Phil Schiller is scaling back his involvement in the company’s events and his supervision of the App Store.

I thought I’d find the oldest Tim Cook photo in my Photos library (what, do you not have numerous Apple executives in your People view?) and it’s from October 2008:

This was from the post-event Q&A session, back when that was a thing!

In the video of this event you’ll see that Tim Cook, then Apple’s COO, is asked by Steve Jobs to present “the state of the Mac.” If you’re used to Cook being more of an emcee for presentations by others in a pre-baked video, you may be amused to see him working hard to present Apple’s Mac lineup to an in-person crowd of media people. (There’s also a Jony Ive live presentation!)

The big product from this event: the unibody MacBook Pro, including an all-button multitouch trackpad.

Happy trails to Tim and Phil, though it sure sounds like they’re still going to be haunting the corridors of Apple Park for years to come.

I know there’s no connection between my local area network and our house’s plumbing system, but when the faucet started running uncontrollably literally seconds after I fixed a network outage, I had to wonder: did we have a poltergeist? The jury is still out. But I can tell you that my hour of fruitless examination of router settings is to your benefit: you won’t have to do this when it happens to you.

The weakest TP-Link

As a guy known for Wi-Fi since the early 2000s, you might think my house is ablaze with wireless signals.¹ Yes, it is: we have six Wi-Fi access points and gateways in a relatively small house by modern standards (about 1,200 sq. ft. on the main floor and 800 in the finished basement). But we also have Ethernet strung through the house to connect most of them, with powerline networking adapters where that doesn’t work due to the ancient and mysterious innards of the walls. The innards’ outsides are covered with heavy, old plaster, which absorbs some of the power of the Wi-Fi signals—hence the large number of emitters.

Normally, this works fine. We have four TP-Link routers, some purchased a while back, and a Netgear Nighthawk as our primary base station, which distributes network addresses and is connected to the fiber-optic ISP router.² When something goes wrong, it’s usually an issue with a router crashing, even though its various green lights remain in a happy state.

This time, something was more deeply wrong. The TP-Link routers showed orange Internet connection lights, which in this case meant they were connected via LAN to the Netgear, but they couldn’t reach the Internet. Perversely, I seemed to be able to connect from my iPhone and my office Mac, which has both Ethernet and Wi-Fi connections active.³

TP-Link has one of the most irritating admin approaches for its routers of nearly any networked product I’ve ever used. You can connect directly, but it’s difficult to store the device’s password because it uses a potentially changing local IP address on your LAN. There’s also a centralized system where you can use an app called Tether or a TP-Link website to log in remotely to a router, even when you’re on the same LAN, rather than finding its local address. Tether also scans the local network, letting you connect even when Internet access is disrupted.

Without the routers “seeing” the Internet, I couldn’t use the website, and Tether worked erratically. I eventually was able to figure out the IP addresses of two of the four routers, connect via a web browser, and find a working password for one of them. (To reset the password, you have to factory reset the router. That’s for a future day.)

But I remained baffled. My ISP gateway was up. My Mac could reach the Internet. The Netgear router seemed to be routing my Mac’s traffic to the Internet. Some of the devices on our network were also connected to the rest of the world. Had my TP-Link routers been compromised? Was something more sophisticated going on? Nope.

It’s coming from inside your smart house

Some of you may be yelling at me from the safe distance of your phone or computer. “Glenn, Glenn, why didn’t you check DNS?” The circulatory system of the Internet may be the IP-addressed traffic that passes over the series of tubes that make up the network. But DNS is the helpful labeling system, like an editorial cartoon that uses captions like “taxes” and “fat cats” to mark characters in an illustration. DNS turns human-readable domain names into the underlying numbers required for connections.

Surely DNS was working? My iPhone, Mac, and other devices were resolving addresses, or turning them from names into numbers. Then I found a clue in Network Time Protocol (NTP), a somewhat obscure bit of plumbing that also makes things tick. When I went to Advanced: Administration: NTP Settings on the Netgear, the last time it had been able to grab the current time and date was hours earlier. That seemed problematic.

Digging more deeply, literally, I found that the dig Unix command couldn’t pull up IP addresses from the Netgear router. On a LAN in which you’re using DHCP to handle local address assignment, your router may require that you enter Internet IP addresses for one or two DNS servers, or it might retrieve them automatically from your ISP. When a device on your network requests an address, the DHCP server assigns an address and tells the device to use the router address for DNS resolution. The router relays your requests to the real DNS server.

I tried dig @10.0.0.1 apple.com (use the router to return the IP address for apple.com) via Terminal on my Mac, and it timed out. I then tried the same lookup using my ISP’s DNS servers. Same timeout. The Mac had no problem with domain lookups, however, nor did my iPhone.

Now comes the time to insert a head-slapping emoji. Some time ago, and I can’t recall how long ago, I set my Netgear router to use my ISP’s primary and secondary DNS addresses. I know many people have switched to Google, Quad9, Cloudflare, or other free, public DNS servers to improve lookup speeds, which, at one point, would have helped speed up network operations tremendously because ISPs invested so little in their DNS operations.

However, using public DNS can cause issues in particular cases. For one, it can confuse content delivery networks (CDNs), which try to guess the closest server to you topologically based on your DNS lookup request to their servers. When that works, you’re getting the shortest path and likely faster throughput. Public DNS can misdirect CDNs, resulting in severe slowdowns in data transfers for big files and with streaming. Much of that has been resolved, but not all of it. I had had some issues, so I reverted from one of the public DNS services to my ISP’s servers. (This has largely been solved now.)

So what happened? My ISP, CenturyLink, must have had a DNS failure. I couldn’t get replies from its DNS servers when I checked (directly or via my router). I found postings later from other CenturyLink customers around the same time, but no public message from the company.

Why did my Mac and iPhone keep resolving? My Mac’s Ethernet connection had a manually set DNS server that was an alternate one provided by my ISP, one that apparently continued to work. I can’t explain the iPhone situation, unless it’s possible that iOS will pull DNS over a cellular connection when it fails over Wi-Fi—I don’t know that it does that, but I don’t have another explanation.

I removed my ISP’s DNS values, replaced them with 1.1.1.1 (Cloudflare) and 8.8.8.8 (Google), clicked Apply, and an hour of my time suddenly was marked on my internal spreadsheet as “wasted.”

Where I went wrong

I’m always trying to learn from my mistakes, particularly because I turn mistakes into opportunities to write columns like this one to save time for you, dear reader. In this case, I was led astray by the half-working network and the fact that, seemingly, only one brand of router in one configuration was failing. I should have remembered to start with DNS—and I will in the future.

If you’ve read this long, I’m sure you’re dying to know about the faucet. I had just finished fixing the network, walked to the freezer, grabbed a fruit-only frozen treat, and was walking across the kitchen when a small stream of water came out of the faucet. I tested the taps. I put the frozen delight back into the freezer, turned off the taps while my spouse was on speaker so we could figure out which tap’s cartridge decided at that moment to give up the ghost, and ordered a replacement. This was another kind of DNS failure: do not spout!

For further reading

While this column may have given you less confidence in me than you had before you read it, I share much more information about Wi-Fi, networking, and troubleshooting in my book Take Control of Wi-Fi Networking and Security.

[Got a question for the column? You can email glenn@sixcolors.com or use /glenn in our subscriber-only Discord community.]

Joe Lemire of Sports Business Journal has a detailed story about how MLB came to hire Jason Weingradt, the developer behind the amazing baseball app Mosaic:

By drawing on public application programming interfaces (APIs) from the league and other sources, Weingradt built an app in TestFlight — Apple’s home for products still in beta — and shared his new creation, Mosaic, by posting on Threads and tagging #buildinpublic to solicit early adopter feedback….

That very same day, MLB Executive Vice President Kenny Gersh received a Slack message from colleagues alerting him to Mosaic and asking if the league’s legal team should get involved. While of course not wanting just any developer to profit from baseball’s IP, Gersh appreciated that this was a controlled environment that required an MLB.tv subscription to access premium features, so he replied, “Not ideal, but it’s not a huge problem yet. Maybe we’ll hire.”

They hired. I know there’s a lot of skepticism out there about whether the big organization will just crush the Little App That Could. To me, it says a lot about MLB’s tech brain trust that they embraced Weingradt and that he’s still dropping incredibly impressive new features into the app on a regular basis.

Go to the linked site.

Read on Six Colors.

Jason Snell is a journalist, podcaster, and Jeopardy! contestant. The editor-in-chief of Macworld for 17 years, he currently runs the Apple-focused website Six Colors and appears regularly on several podcasts, including MacBreak Weekly and Upgrade. His latest podcast, Designed in California, details the 50-year history of Apple over 50 episodes.

We talked to Snell about some of his favorite apps for streamlining his podcasting and writing workflows.

Continue reading on The Mac App Store ↦

Apple’s Friday Night Baseball made its immersive video debut on the Vision Pro Friday, with numerous live immersive cameras scattered around Yankee Stadium for the night’s game between the Yankees and the Red Sox.

Apple has produced a lot of immersive video, including some sports documentaries and a set of live L.A. Lakers games, and it’s been clear that the makers of all that content have assumed that immersive video should be produced more or less like regular sports content: with lots of quick cuts, despite the fact that quick cuts in immersive video can be disorienting in a way that cuts in standard 16:9, 2-D video aren’t.

There’s no clear agreement about the ideal solution. I didn’t mind the reduced pace of the NBA broadcast, which toggled between cameras under each basket, but Stratechery’s Ben Thompson felt strongly that the best option would’ve been a single camera at mid-court, to completely eliminate the disorienting cuts and replicate being at the game in person.

Apple’s approach with baseball, at least based on Friday’s game, seems to lean toward Thompson’s preferred approach—and it does benefit from it. Each half inning was shown from a single camera on the dugout rail next to the on-deck circle, giving a great view of pitcher and hitter and the infield, as well as the goings on right in front of the dugout in foul territory. The camera switched between innings, so you were always viewing from the perspective of the at-bat team’s dugout.

Making it all work better was Apple’s addition of a “virtual jumbotron” floating in the sky, a scoreboard with graphics and a video feed of the standard 16:9 telecast on Apple TV. It was easy to look up and catch a replay or even get a better view of something happening in the far-off outfield, without getting in the way of my view of the game itself.

In between innings, the broadcast stayed in the park—and this is when it would occasionally switch to a different angle, such as at the outfield fence, behind first base, in the club level behind home plate, or looking down into the dugout. There were also replays—carefully demarcated with animated graphics, to reduce confusion—of key plays from the previous inning from the immersive perspective.

In the end, it felt much more like I was sitting at Yankee Stadium watching the game. Apple’s dedicated commentators tried to point out things you couldn’t see if you were watching a standard telecast, like defensive positioning. The commentary was fine (though I wish it had been a bit less chatty), but I would also have been happy to have the option to listen to natural audio, or just the local radio broadcast.

I do wish there had been a little bit more experimentation in terms of the primary camera angle. (Disclosure: I only watched three innings before needing to leave home to catch a flight.) I would’ve been interested in seeing an inning from behind first or third base, just to get a little bit of a different angle.

Still, I think Apple’s first immersive live baseball production was successful. I saw the Yankee catcher commit interference and then get hit in the arm by a brutal backswing; I saw a wide throw from shortstop almost (but not quite) pull the first baseman off the bag. I saw Yankee manager Aaron Boone constantly spitting a stream of sunflower seeds on the warning track in front of the dugout rail. And most delightfully, every few minutes a train zipped past the stadium out in the outfield, visible in a crack between the stands and the scoreboard.

Will immersive sports amount to anything? I don’t think anyone knows, but this latest experiment suggests that the people producing Apple’s immersive sports are actually learning and experimenting. I’m encouraged, and I’ll tune in next week for sure.

Apple’s overhaul of Siri and its expansion of Apple Intelligence are extensive. Take Control publisher Joe Kissell and I looked at this mountain of changes and opted to research and write an entirely new book, Take Control of Siri AI and Apple Intelligence, to help us get a handle on what’s new and thus pass it along to readers. This title is now available in its 1.0 release, ahead of the version 27 operating systems shipping in September. We also have our books on iOS 27/iPadOS 27 and Golden Gate available in 1.0 versions. All will receive free updates when the production versions ship.

We look at everything related to Siri AI, including the new Siri app and its ability to handle contextually aware conversations, the expansion of Apple Intelligence into new apps, enhancements to accessibility features, and, in particular, Visual Intelligence’s heightened prominence as a camera feature on the iPhone and iPad. We also dive into how Apple’s Private Compute Cloud works and associated privacy issues, particularly around the company’s extension of this on-device processing to Apple-managed hardware at Google Cloud.

Go to the linked site.

Read on Six Colors.

Our Mac upgrade plans in the light of price hikes, YouTube view metric changes, our home internet speeds, and how many apps we have our phone.

Go to the podcast page.

Today Relay launched the public and private feeds of my new podcast, Designed in California. If you’re interested in the history of Apple, check it out. The first few episodes in the feed are episodes we previously released in the Upgrade podcast feed; our first all-new episode debuts next week.

If you’re a Kickstarter backer who pledged at a level where you’ll get the special member feeds, check your messages for information about how to redeem that pledge and get access to the special feeds.

And if you didn’t back the Kickstarter, you can now join us via Relay and get access to entire series of the show all at once, ad free. Next week, members will receive the entirety of our series about Apple’s mid-90s Mac OS crisis that led to the company buying NeXT and bringing back Steve Jobs, which led to the creation of Mac OS X. Those episodes will play out over the next six weeks in the main feed, but members will get all seven episodes, five hours and 15 minutes of content, all at once. (Plus the first of our monthly bonus episodes.)

There’s also a YouTube channel, and Spotify users will find that video version available within Spotify as well.

Go to the linked site.

Read on Six Colors.