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(Podcast) Upgrade 626: Unprecedented Weirdness

2026-06-30 05:39:58

Apple raised prices! Is this a shocking move, or were Apple products just sneakily affordable before? (And can it be both?) We also parse Mark Gurman’s reports on Apple skipping over may M6 chips to go directly to M7.

Go to the podcast page.

My credit card number? Sure! It’s 4242 4242 4242 4242

2026-06-30 01:00:37

Glenn Fleishman, art by Shafer Brown

We live in a modern, jet-set, hyper-fast world! When we want to buy something online, boom, zoom, we use our fingerprint or face to approve the transaction, so we can grab the next Segway outta here! We don’t have time to enter a credit card! And can we trust a webpage form? Pfeh!

All right, calm down, 1950s inner voice, it’s not that bad. Most of our transactions involving a payment card or other sensitive data can be safely handled over a secure web connection. Apple Pay in Safari is the highest standard, of course, because the payment process involves encrypted elements, and your card number isn’t disclosed to the merchant. The Wallet app in iOS and the Wallet features in iPadOS and macOS further let us automate the entry of numbers and identifiers on pages we trust.

That’s all for automated commerce. What about other scenarios where you need to provide information to someone, often a friend or a local business, in order to transfer money or conduct a transaction? How can you be sure no one else is snooping in?

Make a call

Voice is still one of the most secure means of providing data. The landline wired and cellular wireless networks may be fertile ground for government agencies, but if you need to read a credit-card number or provide a PIN, a call is often the safest way to do so. By voice, you can always have the other person verify details that you believe only they know, or you can verify details to them for the same.

Old-fashioned candlestick style dial-telephone in front of a framed
One ringy-dingy. (Photo by Jez Timms on Unsplash)

Because we live in a cyberpunk dystopian future, I do have to add a proviso. AI-generated voices have been convincing for a couple of years now—long enough that you shouldn’t trust an incoming call from someone you think you know, and certainly not from a bank, credit-card company, or other financial institution. I mean, I wrote “How To Avoid AI Voice Impersonation and Similar Scams” in January 2024! I assume the state-of-the-art scam is even better.

(The biggest takeaway is analog, too. Set a family password that you demand from a family member who calls asking for money or to do some weird phone or computer set of instructions.1)

Unless recorded, voice calls also lack persistence, making them impossible to recover later. A real-time Bob needs to be either between Alice and Carol or doing an AI impression of Alice or Carol.

Use secure messaging

I could make the argument that using secure messaging carries even less risk than a voice call if you’ve had an ongoing messaging conversation with someone, so you know it’s really them. Are unsecured text messages being intercepted willy-nilly?2 No, but there is also something about sending plain text all over the cellular networks that gives me the willies, nillies aside.

Composite figure showing text in Messages app to reveal RCS and iMessage encrypted status
Look for a lock and the label Encrypted for RCS; iMessage is always encrypted, or it won’t work. (Lower image: Apple)

Secure messaging systems include:

  • iMessage: While iMessage has seen exploits, they’re government-grade ones. Its secure end-to-end infrastructure is creaky, but unbroken. There’s an extra detail I’ll mention below.
  • RCS with encryption: Between Apple Messages on iOS 26.5 or later and an Android device with RCS encryption support, you have a similar level of end-to-end protection. Make sure you see RCS encryption in the text field, or it’s just plain text. You can also use RCS encryption between two capable Android devices—as if!
  • Signal: The Signal app and ecosystem have the best end-to-end encryption, as it implements some of the most modern approaches to protecting older messages and current conversations available so far.

The extra note on iMessage is complicated. Briefly, if you use Messages in iCloud, an encryption key to retrieve those messages is included in an iCloud-based iPhone or iPad backup. With access to your Apple Account, someone could potentially retrieve your stored messages. However, if you enable iCloud’s Advanced Data Protection, the backup is encrypted and requires endpoint decryption using one of your devices, protecting the Messages in iCloud encryption key. This should be a worry only if someone manages to obtain your Apple Account, can activate a second factor, and the information you passed via Messages is so sensitive that someone would hunt to uncover it.

Avoid using SMS or MMS text messages (unencrypted plain text), unencrypted RCS (in-transit/at-rest encryption), or other messaging systems where you’re not sure how they handle data protection. WhatsApp can be used if you either have backups disabled or have enabled end-to-end encrypted backups.

Don’t use most collaborative tools

I know that I spend a lot of time in shared documents, whether Google Docs, Notes, Pages, or more esoteric apps or web apps. Most lack the highest level of protection. Shared Pages and Numbers files on iCloud Drive, as well as Google Docs, are encrypted in transit and at rest, and granting shared access is relatively easy (very easy in Google Docs). For iCloud Drive documents, this is true even with Advanced Data Protection enabled.

I’d be dubious about pasting my driver’s license or credit-card information into any of them that are shared with someone else. Ditto, don’t take a picture of your payment card or driver’s license and share it via a Shared Album in Photos, as it has the same issue.

There are two notable (heh) exceptions: if you and the other party or parties to a shared Notes entry or an iCloud Shared Photo Library all have Advanced Data Protection enabled, end-to-end encryption is used.

Consider the risk

As with all decisions around privacy, consider how at risk you and your data are, including voice as data. In most cases, ensuring a baseline level of encryption can be enough. Even when the app or server can “see” your unscrambled information, the transport between your device and the server and another person’s device is encrypted. Someone would have to break into the server to sniff data. If stored on the server, the baseline state would be encrypted at rest; however, the server operator would manage those encryption keys.

For peace of mind, if not strictly necessary, I’d encourage you to consider using end-to-end encryption when you can. It’s so easily available. For someone to crack your connection, they would need to obtain one of your devices and be able to unlock it. Otherwise, the path between you and someone else is effectively impregnable.

For further reading

I cover message security extensively in my book Take Control of FaceTime and Messages, which I recently updated to include the beta release of RCS encryption for Apple-to-Android communication.

For more on Wallet, I wrote an entire book on that seemingly simple app and set of features, Take Control of Apple Wallet. The book arose from the frustrations of finding where things in Wallet (and outside Wallet but related to it) lived.

On the security side of things, Take Control of Securing Your Apple Devices includes detailed advice on the ins and outs of physical security: how to ensure someone with access to your hardware can’t reach your data.

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


  1. This will also deter family members from asking you for money if you don’t give them the password. 
  2. If so, who is Willy? 

(Sponsor) Mojave Paint

2026-06-27 02:00:49

My thanks to Mojave Paint for sponsoring Six Colors this week. Mojave Paint is a new macOS image editor for power users that will feel really familiar (in the best possible way). If you use layers, masks, channels, selections, adjustments and filters all in the same editing session, Mojave Paint might be for you.

There’s so much you can do with Mojave Paint. Make pixel art. Clean up document scans. Design a flyer. Create App Store screenshots. Crop and resize photos. Do some basic photo retouching. Remove a background.

Mojave Paint is powerful, but it’s also got a simple, uncluttered UI reminiscent of the best software of the 1990s. Yes, it’s retro—but it’s also practical, since hard-edged 1x pixel graphics are high contrast and communicate precision.

Mojave Paint is available in the Mac App Store as a free download. That’s the limited version, but it’s only $9.99 to fully unlock all the features.

Level Lock founders and engineers kicked by parent company ↦

2026-06-27 02:00:46

Smart home reporter Jennifer Pattison Tuohy at The Verge reports that parent company Assa Abloy has folded Level, which it acquired in 2024, into its Kwikset brand and removed the company’s founders:

The Verge obtained exclusive details from a person familiar with the restructuring who requested anonymity as they were part of the layoffs. They shared an audio recording of a meeting in which Peter Boriskin, CTO for Assa Abloy North America, and Kimberly Cummins, head of North American HR, informed the staff that their positions had been eliminated, effective immediately, as “a part of a larger restructuring of the Level business.” A LinkedIn post from a now-former employee corroborates the layoffs.

As an owner and daily user of three Level locks, this news is certainly worrying. An Assa Abloy spokesperson told The Verge that the company will “continue to develop and sell the Level Lock platform and hardware” but given that the majority of the engineering team seems to also be out, there are certainly questions around it.

On the upside, all of Level’s products now support Matter, which means that at least basic functionality ought to continue working for some time to come. But this is still potentially a disappointing move for a unique product.

Go to the linked site.

Read on Six Colors.

Apple should free the macOS icons from squircle jail ↦

2026-06-27 01:59:15

Rogue Amoeba’s Paul Kafasis is encouraged by the interface improvements Apple is making in macOS 27, but points out that there’s still one huge issue from last year that needs to be resolved, namely forcing all Mac icons to be trapped inside a single, uniform shape:

Apple’s prohibition on shapes is a step backward for both usability and creativity in app icons. Icons are now harder to distinguish because they’re no longer allowed to be distinctive. But there’s no technical reason for it. Apple could, and should, once again allow icons to take on a wide variety of shapes.

It’s clear that some people within Apple recognize that the transition to Liquid Glass introduced mistakes. They also appear to have the authority to fix those mistakes. Refinements to Apple’s own icons in Golden Gate are a welcome course correction, as is the much-celebrated Liquid Glass opacity slider. It’s time to correct the mistake of banning icon shapes as well.

Kafasis makes the important point that uniform shapes make it more difficult for users, especially those with vision issues including color deficiency, to differentiate between icons. He also references an argument from TidBITS’s Adam Engst that the uniformity sabotages Apple’s own clear and tinted icon formats.

Apple, let the Mac app icons be free.

Go to the linked site.

Read on Six Colors.

Report: Apple changes chip and OLED MacBook Pro release plans

2026-06-27 01:51:11

Diverse group around white table indoors with brick wall and glass doors, holding cameras, phones, and laptops including Apple devices, documenting an event.
An Apple laptop media event.

Perhaps lost a bit amid the Apple price hikes of Thursday was this surprising bit of news from Bloomberg’s Mark Gurman regarding the future of Apple silicon Macs:

[Apple] plans to debut a base M6 processor as early as this year for entry-level Macs, according to people with knowledge of the matter. But in a first, the company will skip higher-end versions of that chip, said the people, who asked not to be identified because the plans are private.

Apple instead aims to introduce its next Pro and Max chips with more advanced computing and graphics power in 2027 as part of a new M7 generation, according to the people.

According to Gurman, Apple has decided to shift gears in order to fast-track the tech in the M7 chips, which is better suited to “meet growing demand for on-device AI capabilities and more graphics-intensive software.” In other words, Apple looked at its chip roadmap and felt it didn’t want to wait for M7 and didn’t want to bother shipping M6 Pro and Max.

As weird as this seems, I’m actually encouraged by Apple’s willingness to change its chip and product plans in order to better serve the technical needs of its customers. If Apple has a chance to push its advantage when it comes to on-device AI processing, it should do so, even if it means ripping up plans and calling an audible.

Of course, this decision has knock-on effects. For example, Gurman’s been reporting for ages about Apple’s forthcoming MacBook Pro models with OLED touchscreens—but the chips they were meant to ship with, the M6 Pro and M6 Max, have just been cancelled! So… now what?

On Friday, Gurman let the other shoe drop, reporting that Apple will release those systems with M5 chips “between late this year and early next year”, with M7 to follow:

Apple is already conducting advanced testing of the follow-up models with M7 Pro and M7 Max chips, according to the people. Those laptop models are planned for as early as the end of 2027. Apple is also planning a Mac Studio refresh with M7 Max and M7 Ultra chips in 2028.

Releasing new models with familiar chips is probably not ideal, but if the alternative is delaying the OLED MacBook Pro until late 2027, I can see why Apple would choose to go ahead and roll out a new and improved MacBook Pro powered by the M5 Pro and M5 Max. The laptop is apparently just about ready, so there’s no sense waiting. The weirdness of it launching with an old chip is just collateral damage from Apple’s larger decision to be more aggressive when it comes to its high-end chip plans.