Author Archives: mike

How to Share Sensitive Information Securely over the Internet

At some point, most of our communications shifted from analog to digital: letters and phone calls became emails, texts, and video calls. With analog methods, we could generally assume that our private communications would remain private. Few people were going to steam open a letter or wiretap a phone line. The Internet changed that—digital communications, if not properly protected, can be intercepted in bulk far more easily.

Not all everyday communications require strict privacy. Most of us prefer privacy, of course—few people want their dinner plans published for the world to see—but there are typically no consequences of exposure greater than mild embarrassment (McDonald’s again?). But even ordinary people regularly need to share information that could damage their relationships, finances, or careers if it fell into the wrong hands.

Passwords are the most obvious example because their entire point is secrecy. But other sensitive data includes credit card details, bank account numbers, tax documents, retirement planning materials, and health-related information. When you need to share such data, how do you do it securely?

Data at Rest and in Transit

Before exploring specific solutions, you need to think about how information is protected when it’s in transit between systems and when it’s stored somewhere:

In transit: To prevent eavesdropping, focus on communication channels that are encrypted between you and the destination:

  • Between your app and a server: Nearly all Internet-enabled apps, including all Web browsers, use SSL/TLS to protect their connections to servers. A lock icon in a Web browser’s address bar indicates HTTPS encryption, or you can look for https at the start of a website’s URL.
  • End-to-end encryption: Even better is end-to-end encryption, which ensures that not even the service provider can decrypt your traffic. iMessage (blue-bubble conversations), WhatsApp, and Signal provide end-to-end encryption protection (though WhatsApp archives are readable by other Meta apps). SMS messages are not encrypted at all, and RCS conversations only support encryption with the latest Apple and Google updates, plus carrier support. Both SMS and RCS appear as green-bubble conversations.

At rest: Stored data—whether on your computer, at remote email servers, or in the cloud—needs protection too. Two approaches help:

  • Per-file encryption: Encrypt data before sending so even if an attacker figures out how to access the file, it can’t be decrypted without a password. Send the password through a completely different communication channel (called “out-of-band”)—for example, share an encrypted file via email but send the password via Messages.
  • Time- or access-expiring links: Send a link to the information that expires after a short period or after a limited number of views, thereby shrinking the window during which a breach could occur.

Choosing the Right Solution

The best approach for any given communication depends on four factors:

  • Audience: What are your recipients’ technical capabilities? Messages is easy and secure, but only Apple users can access it. Email reaches everyone but offers less protection. A password-protected PDF is probably easier for less-technical users than an encrypted disk image.
  • Content type: Sharing a password differs from sharing a document, which in turn is different from sharing a collection of files.
  • Importance: How problematic would it be if the sensitive information you’re sharing fell into the wrong hands? There’s a world of difference between the password for a club discussion forum and the credentials to your retirement account.
  • Persistence: Does your recipient need to glance at something only once, or do they need to retain a copy permanently?

Eight Secure Sharing Methods

With all that in mind, here are eight secure methods of sharing information that you can employ in different situations:

  1. Use a secure portal when available: Doctors, lawyers, accountants, and other professionals who regularly receive sensitive information often use secure customer portals or services like DocuSign for sending messages, documents, and files. Use whatever system they provide unless you have good reason to doubt their IT competence.
  2. iMessage, Signal, or WhatsApp: For quick sharing of sensitive information, these end-to-end encrypted messaging services work well. They’re particularly useful for sending information that isn’t useful on its own—for instance, send a login URL and username via email but the password separately via Messages.
  3. Self-destructing links: Services like 1ty.me and One-Time Secret generate encrypted links that contain text. Once the recipient views the link, the server deletes the data, and the link self-destructs. If the recipient reports the link was already used, you know it was compromised. Be aware that some email systems automatically scan links, which could trigger premature self-destruction.
  4. Password manager sharing: 1Password, Bitwarden, and some other password managers (but not Apple’s Passwords) offer secure sharing features that make it easy to share credentials with someone who needs to access a particular account. You can create links with expiration dates, limit access to specific email addresses, and cause links to self-destruct after being viewed once.
  5. Password-protected PDF: For documents that could be printed, create a password-protected PDF. From nearly any app, choose File > Print, click the PDF menu at the bottom, and choose Save As PDF. In the Save dialog that appears, click Security Options, select “Require password to open document,” and enter a strong password (online services can remove weak passwords). Share the file however you like, but send the password through a different channel, preferably via an expiring link.
  6. Password-protected disk image: For Mac users sharing files that can’t easily become PDFs, or for sharing collections of files, create a password-protected disk image. In Disk Utility, create a new compressed disk image (File > New Image > Image from Folder), choose an encryption option (256-bit for more sensitive information), and enter a strong password. Again, share the password separately, ideally via an expiring link.
  7. Password-protected Zip archive: A password-protected Zip archive serves the same purpose and may be easier for Windows users to extract. Apps like Keka and BetterZip can create these. For the fastest approach, open Terminal, type zip -er ~/Desktop/filename.zip (with a space at the end), drag in the files you want to compress, press Return, and enter your desired password when prompted.
  8. Time-expiring cloud storage links: Some cloud storage services offer links that expire after a specified time. Dropbox Professional supports this feature, enabling you to share files while ensuring that links become useless in the event of a breach.

There’s no one-size-fits-all solution for securely sharing sensitive information. Match your approach to the sensitivity of the data, your recipient’s capabilities, and how long they need access.

(Featured image by iStock.com/metamorworks)

Control Center Is Improved—and Highly Customizable—in macOS 26 Tahoe

Control Center debuted on the iPhone over a decade ago in iOS 7 and made its way to the Mac in 2020 with macOS 11 Big Sur. However, through macOS 15 Sequoia, Mac users who wanted to tweak Control Center for their needs were limited to turning specific controls on or off. With macOS 26 Tahoe, Apple completely overhauled Control Center, enabling users to remove, rearrange, and add controls, including new ones from independent developers.

If you mostly ignore Control Center on your Mac, it’s worth another look in Tahoe. The big win of Control Center is that it provides quick access to numerous controls without occupying valuable space in the menu bar, a limitation that MacBook users regularly encounter. Now that you can personalize Control Center, it’s much more useful than before.

Before we explain how to customize Control Center, let’s look at the basics.

Open and Use Control Center

To open Control Center, click its icon at the right side of the menu bar or use its Fn-C keyboard shortcut. It always appears in the top-right corner of the screen (below left). You may notice a colored dot next to the Control Center icon: orange means the microphone is in use, green tells you a camera is in use, purple indicates that system audio is being recorded, and an arrow means an app is using your location.

Some controls, like Dark Mode and Screenshot, are simple buttons that you click to toggle a setting or trigger an action. You’ll also see sliders, such as for Display Brightness and Sound Volume. Many controls, such as Display, open separate panels with additional controls (below right).

Customize Control Center

To begin customizing Control Center, don’t look in System Settings anymore—instead, click the Edit Controls button at the bottom of Control Center. That displays a ⊖ button on each control, adds eight empty single-button slots at the bottom, and opens the Control library.

Once here, you can:

  • Remove existing controls: Click a control’s ⊖ button to remove it from Control Center. You can always put it back later, although the lack of a label in Control Center can make it tricky to find in the Control library, because you may not know what you removed.
  • Resize controls: You can usually resize a control by Control-clicking it and choosing Small, Medium, or Large. Small controls occupy a single slot; medium controls occupy two side-by-side slots; and large controls occupy four slots, either as a 2-by-2 grid or a 4-by-1 line.
  • Rearrange the order: Drag controls in the grid to reorder them. You can move one only to a position where it’ll fit, so you may need to resize other controls to make space.
  • Add new controls: More on this below, but in short, you add new controls from the Control library window that appears to the left of Control Center when you click Edit Controls.

When you’re finished customizing Control Center in these ways, click Done at the bottom of the Control library.

Adding Controls to Control Center

Apple gives you two ways to add controls from the Control library:

  • Drag a control in the main pane to the desired Control Center spot.
  • Hover over the desired control, click the green ⊕ button that appears, and choose Add to Control Center. You can also choose Add to Menu Bar to put the control there for even quicker access.

To discover what controls are available, either scroll through the All Controls collection or select a particular category in the sidebar. You can also search for controls by name.

Nearly all the controls have been added to the library in advance by Apple, but there are two exceptions:

  • Third-party controls: Independent developers can create their own. For instance, Flexibits’ Cardhop provides controls for adding and searching for contacts.
  • Shortcuts: Apple’s automation app, Shortcuts, enables you to open any app from Control Center, run any shortcut, or show a collection of shortcuts. Anything you can create in Shortcuts can be triggered from Control Center. (Don’t be intimidated by Shortcuts; you can ask any AI chatbot to help you develop a shortcut.)

Don’t worry about messing up Control Center while you’re experimenting with different controls. You can always reset it in System Settings > Menu Bar by scrolling to the bottom and clicking Reset Control Center.

One final tip. A little control may appear at the top of Control Center at times. It’s a privacy notification that tells you whether an app has used your location recently (like Weather), used the camera (like FaceTime), recorded your screen (like Screenshot), or engaged in some other activity Apple thinks you might want to know about. Click it to learn a little more.

(Featured image based on an original by iStock.com/guteksk7)

Understanding AI Today: No Longer Just a Chatbot

When ChatGPT launched in late 2022, using it was simple: you typed a prompt, and it generated text in response. That text came from a statistical model trained on data available at the time. If you asked ChatGPT about anything that had happened more recently, it either couldn’t help or would confidently make stuff up.

The chat interface that today’s AI systems still rely on has become more of a control panel than the system itself. What happens after you press Return may involve Web searches, file analysis, code execution, connected accounts, and even digital-world actions—all orchestrated behind the scenes. You need to understand what’s happening behind the chat box to evaluate the accuracy, quality, and utility of the answers that appear there.

Under the Hood of an AI System

The capabilities of a modern AI system include:

  • Models generate text, analyze images, and work through problems. This is the traditional “AI” part, but it has improved hugely through better training techniques, longer conversations and documents, and extended reasoning time. Cutoff dates for training models remain an issue—some AIs think macOS 26 is still in beta.
  • Retrieval pulls information from the Web, uploaded documents, or connected data sources. When an AI cites a source, it’s usually because retrieval happened. However, it’s still essential to check cited sources carefully because the URLs may be broken, and even when pages exist, they may not support the claims.
  • Tools handle tasks the model can’t do on its own, such as analyzing numeric data, running code, creating visualizations, or searching databases. For many types of requests, the AI will write a script or call a tool to handle the work, dramatically increasing the likelihood that the results will be correct and making it easier to refine them.
  • Connectors link AI systems to external platforms such as email, calendars, file storage, and Internet-hosted applications. They’re necessary so a system can work on personalized data (“Give me a timeline of the deliverables on the MacDavis project from our email conversations.”) and to connect with business data.
  • Actions let AI systems do things in the digital world: send messages, create events, modify files, and interact with other software. Here is where AI stops merely advising and starts affecting real systems, so the safeguards need to be much stronger.

These capabilities don’t always appear together. A simple chatbot exchange may rely only on the model’s training. A research request may add retrieval and tools so the AI can search current sources, summarize what it finds, and run calculations or create charts. A workplace copilot may add connectors to email, calendars, cloud storage, customer records, or internal databases. A full-fledged agent adds actions, enabling the system to operate on your behalf.

It’s important to understand all the possibilities because each layer changes both what the AI can do and how much you should trust it. A model-only answer calls for skepticism (and perhaps a search). A search-based answer needs source checking. A tool-generated answer requires checking the inputs, method, and results. A connector-based answer warrants attention to the source of the data (and whether the permissions are too broad). And an action deserves a preview, an approval process, and ideally a way to undo mistakes.

What This Means for Trust, Privacy, and Control

This evolution from chatbot to assistant generally yields better results, but it also comes with new risks:

  • Privacy isn’t just about what you type. It’s about what files you upload, what accounts you connect, and what the AI system can access. Putting confidential data into an AI could be problematic in numerous ways, not least regulatory compliance.
  • Accuracy varies by task. Responses drawn purely from training data may be outdated or flat-out wrong, while search-informed answers reflect current sources. Asking an AI to “Confirm with a search” is a good way to get it to reassess what it has written with current information.
  • Actions have consequences. When AI can send email, modify files, change settings, or interact with business systems, mistakes can have outsized impacts. This is why we strongly recommend caution about OpenClaw-style agents: giving any AI broad access to email, messaging, calendars, files, and applications creates security and reliability risks. Always preview any action—or AI-generated script you’re running externally—whose results could be difficult or impossible to reverse.
  • Confidence isn’t correctness. AI outputs can sound polished and authoritative even when they contain errors, outdated information, or subtle misunderstandings of your intent. Any AI-generated work that informs decisions or will be seen by others deserves human review. Just as you wouldn’t base anything important on the work of a summer intern without checking first, you don’t want AI-generated work to go out if you can’t stand behind it.

For individuals, how you react to these risks mostly comes down to verification and restraint: check important sources, review important outputs, and don’t let AI take irreversible actions without approval. For organizations, the same principles must become policy because employees may already be using AI tools with company data without IT’s knowledge. To get ahead of the issue, organizations should:

  • Audit what’s already happening. Talk with employees to find out what they’re already using, inventory online apps with embedded AI features, and check browser extensions, which often fly under the radar.
  • Classify workflows by risk. Not all workflows need the same level of attention. Low-stakes tasks like brainstorming and text editing can proceed with commonsense guidelines. High-stakes outputs—client communications, financial analysis, security configurations—need human review before they go live.
  • Evaluate tools carefully. Before approving any AI tool for general use, understand what data it accesses, whether it trains on your inputs, what actions it can take, and what logging is available. Most paid tools won’t train on your data, or can at least be configured not to, but the more important your data, the deeper your research should go.
  • Create clear policies and train employees. Define which tools are approved, what data can be entered into AI systems, when human review is required, and what’s prohibited. Employees need practical guidance on how to apply the policies to their actual workflows. Don’t assume that an email or two is sufficient—training is essential.

The biggest mistake people make about AI today is underestimating both its risks and rewards because they’re still thinking about ChatGPT from 2023. The chat box may look the same, but it now sits in front of systems that are vastly more powerful, meaning that it’s more important than ever to consider when to trust them, when to verify them, and when to keep them at arm’s length.

(Featured image by iStock.com/tadamichi)

Drag Documents to Apps in the macOS App Switcher

You undoubtedly know about pressing Command-Tab to bring up the macOS App Switcher and mousing to the app you want to switch to. Keyboard jockeys probably even know to keep holding Command down while pressing Tab or right-arrow to cycle to the right (press Shift-Tab, the grave accent/tilde key, or left-arrow to cycle to the left), before releasing the Command key to switch. But did you know you can start dragging something—say a document from the Finder—with your right hand, press Command-Tab with your left hand, and then drop the document on an app in the App Switcher to open it? Go ahead, give it a try!

(Featured image generated by Adam Engst with ChatGPT)

Apple Raises Prices on Macs and iPads, but not iPhones or Apple Watches… Yet

There’s no way to put a positive spin on this: Apple has raised prices across most of its product lineup, with increases averaging 20% on Macs, iPads, HomePods, the Apple TV, and even the Vision Pro. The iPhone and Apple Watch remain unaffected… for now.

The price hikes took effect on June 25. In a statement to the press, Apple blamed the AI industry’s insatiable appetite for memory chips, which has caused prices for memory and storage to increase up to sixfold:

The consumer electronics industry is facing an unprecedented challenge. The rapid expansion of AI data centers has created an extraordinary surge in demand for memory and storage. We have never seen a component price increase this much, this quickly. We have shielded our customers from these increases so far, but we have now reached a point where we need to begin raising prices on a number of products.

Apple’s price increases vary widely. The base model of the Apple TV 4K took the biggest percentage hit, jumping from $129 to $199—a 54% increase that’s particularly puzzling given the device has only 64 GB of storage and 4 GB of memory. It may be setting a new price floor for the next-generation Apple TV. At the other end of the percentage increase spectrum, the Vision Pro rose just 6%, from $3,499 to $3,699.

Mac and iPad Price Changes

The Mac lineup saw significant increases at both the low and high ends:

  • MacBook Neo: $599 → $699 (+17%)
  • MacBook Air (13-inch): $1,099 → $1,299 (+18%)
  • MacBook Pro (14-inch base): $1,699 → $1,999 (+18%)
  • Mac mini (M4): $599 → $799 (+33%)
  • Mac Studio (M3 Ultra): $3,999 → $5,299 (+33%)

The $1,300 increase for the M3 Ultra model of the Mac Studio is the largest absolute dollar jump in the lineup—a reflection of just how much high-memory configurations are affected by the shortage.

iPads saw increases of 15–30%, with the base iPad hit hardest:

  • iPad: $349 → $449 (+29%)
  • iPad mini: $499 → $599 (+20%)
  • iPad Air (11-inch): $599 → $749 (+25%)
  • iPad Air (13-inch): $799 → $949 (+19%)
  • iPad Pro (11-inch): $999 → $1,199 (+20%)
  • iPad Pro (13-inch): $1,299 → $1,499 (+15%)

Base prices tell only part of the story. Memory and storage upgrade prices also jumped dramatically, with the 64 GB and 128 GB memory upgrades for M5 Max models of the MacBook Pro doubling in price.

Why iPhones and Apple Watches Were Spared

Apple left the prices for the iPhone, Apple Watch, AirPods, and Studio Display unchanged. The Studio Displays and AirPods likely escaped because they use minimal memory. The iPhone and Apple Watch are a different story—Apple may be willing to accept lower margins on its flagship products, betting that stable prices will drive enough additional sales to offset reduced profit per unit.

There’s also the timing factor. New iPhone and Apple Watch models are expected in September, and rumors suggest Apple will introduce only high-end (and higher margin) iPhone 18 models then, with more affordable models held until early 2027. That makes buying a current-generation iPhone now potentially the better deal—new models will almost certainly debut at higher prices.

Apple Isn’t Alone

The memory crisis has hit the entire consumer electronics industry. Microsoft raised prices on all Surface PCs. Samsung is raising prices on its Galaxy smartphones. Lenovo, HP, and Dell have all raised laptop prices.

The culprit is the industry’s rapid expansion into AI. Data centers are consuming memory and storage at a pace the industry wasn’t equipped to handle. Memory chip suppliers like Micron, Samsung, and SK Hynix have directed production toward AI chipmakers like Nvidia, who are willing to pay top dollar, leaving consumer electronics to compete for whatever remains. Industry observers expect the shortage to persist through at least 2027 due to the time required to build manufacturing capacity.

What Should You Do?

If you need a Mac or iPad, some retailers may not have updated prices yet, but that won’t last. Similarly, you could look for a refurbished Mac from Apple or a certified pre-owned Mac from retailers like OWC, but those prices have largely increased as well.

For the iPhone and Apple Watch, the calculus is unusual: normally, we’d encourage waiting for September’s new models, but this year, buying now at current prices may save you some money.

Ultimately, the only options may be to bite the bullet and pay current prices, buy a less-expensive model or configuration, or hold on to your existing hardware in the hopes that prices come back down.

(Featured image generated by Adam Engst with ChatGPT)

Use Fake Contacts to Improve Dictation Accuracy

Apple’s Dictation feature is a great way to avoid slow typing on the iPhone and iPad, and it can be welcome on the Mac as well. But it struggles with proper nouns—it guesses wildly at unfamiliar names and often fails to capitalize common words that are part of a name (so you get “New York Public library”). Apple doesn’t provide a user-editable dictionary, but there’s a workaround solution: create entries in Contacts. When you create a fake contact for a troublesome word or phrase, Dictation learns to recognize it correctly across all your Apple devices. Put the word or phrase in the First Name field and add an emoji like 🙉 in the Last Name field so these fake contacts sort to the bottom of your Contacts list and don’t clutter the display. For stubborn words, you may need to train Dictation by dictating a few practice sentences in Notes and correcting mistakes when iOS offers alternatives. This trick works for place names, organization names, technical terms, or any word that Dictation consistently gets wrong.

(Featured image by iStock.com/Jacob Wackerhausen)

When Should You Upgrade Your Apple Devices?

The simple answer to “When should you upgrade?” is when your device no longer does what you need, or when you want something new. But that’s not helpful if you’re trying to make an informed decision—is there a sweet spot when it makes more sense to upgrade rather than squeeze another year out of your current device?

The answer is yes, and the specifics depend on the type of device, whether it’s used for work or personal tasks, and how central it is to your daily life. Here’s our advice, including recommended timeframes and the warning signs that suggest it’s time to upgrade.

Mac Upgrade Cycles

Macs boast impressive longevity, particularly those with Apple silicon. With proper care, a Mac can easily remain productive for 5–7 years, though business environments typically benefit from shorter replacement cycles. Apple provides security updates for the current macOS version and the two previous versions, giving you roughly 2 years of security updates after a Mac loses support for the newest macOS.

For business use, we recommend a 3–5 year replacement cycle. Research shows that hardware problems increase after this point, performance lags compared to current machines, and resale value drops. The loss of productivity from slow performance and downtime outweighs the cost of a new Mac. If you don’t already have one, make an inventory of all your Macs, including purchase dates, and use it to create a replacement schedule. Also consider shuffling Macs around—an employee doing video work might get annual upgrades to the most powerful Mac available, with their old machines handed down to others.

Consider upgrading a Mac when:

  • It no longer receives security updates: Once security updates stop, the Mac becomes increasingly vulnerable to attack. Intel-based Macs are coming due here—macOS 26 Tahoe is the last version to support them, so security updates will end in 2028.
  • Its battery no longer holds a reasonable charge: For MacBooks, battery degradation often drives upgrade decisions. Although Apple will replace the battery for $149–$249, it’s usually more effective to upgrade the entire MacBook.
  • Performance hampers productivity: If apps launch slowly, you see the spinning beach ball regularly, or you find yourself waiting on the computer throughout the day, a newer Mac will increase your productivity.
  • Storage is perpetually low: Running low on storage can reduce performance, block software updates, and force distracting cleanups. If you can’t offload files to external or cloud storage, consider upgrading to a Mac with more capacity.

For personal Macs, you can extend the replacement cycle to 5–7 years or even more as long as the Mac meets your needs and continues to receive security updates.

iPhone Upgrade Cycles

Despite the rough treatment they often receive, iPhones are remarkably durable, with many users keeping them for 4–5 years without significant issues. Apple typically supports iPhones with software updates for 5–6 years after release, making them the longest-supported smartphones on the market.

For business use, we recommend a 3-year replacement cycle. That ensures employees always have devices that support the latest security features and iOS capabilities, including Apple Intelligence, which requires an iPhone 15 Pro or later. A 3-year cycle also means better resale or trade-in value—iPhones depreciate more gracefully than most technology, but that advantage diminishes after the third year.

For personal use, replace your iPhone when:

  • Battery health drops below 80%: Check in Settings > Battery > Battery Health. Below 80%, you’ll notice significant performance throttling and shortened battery life. Replacing the battery for $69–$119 through Apple—it’s best to avoid third-party replacements—can extend a phone’s life by another 2–3 years if everything else works well.
  • It no longer receives iOS updates: Once security updates stop, it’s worth considering replacing it. Typically, Apple releases updates only for the current version of iOS, but this year, it has been providing iOS 18 security fixes for the iPhone XR and XS models, and even released a few critical security updates as far back as iOS 15 and iOS 16.
  • Storage is consistently full: If you’ve enabled Optimize iPhone Storage (Settings > Apps > Photos), turned on Offload Unused Apps (Settings > Apps > App Store), and are still frequently managing storage to make room for new photos, videos, and iOS updates, it’s time to upgrade.
  • The camera no longer meets your needs: Camera improvements have been substantial year over year. If photography matters to you and your iPhone is more than 3–4 years old, a new model will deliver noticeably better results.

iPad Upgrade Cycles

iPads have a longer practical lifespan than Macs or iPhones. It’s not unusual for an iPad to remain useful for 6–7 years, particularly for basic tasks like Web browsing, email, video streaming, and reading.

The upgrade trigger for iPads is usually one of three things:

  • Battery life has declined noticeably: iPads from 2024 and later (starting with the M4 iPad Pro, M2 iPad Air, A17 Pro iPad mini, and A16 iPad) display battery health in Settings > Battery > Battery Health. For older iPads, you can check battery health using Mac apps like coconutBattery or iMazing. If capacity has dropped below 80% or the iPad no longer holds a charge through a typical session, it’s time to upgrade. Apple offers iPad battery replacement for $99–$199, but upgrading may make more financial sense.
  • Performance becomes frustrating: iPads used for demanding tasks like video editing, illustration, or running multiple apps will show their age faster than those used for content consumption.
  • Software support ends: Apple supports iPads for roughly 5–6 years. Once updates stop, security risks increase.

For business use with demanding workflows, a 3–5 year cycle makes sense. For general business use (email, documents, presentations), an older iPad will probably work well enough for 5–6 years. Personal iPads used primarily for media consumption can last until software support ends.

Apple Watch Upgrade Cycles

Apple Watch upgrade cycles depend heavily on how you use the device. Battery degradation is the primary limiting factor—most users report noticeable battery decline after 3–4 years of daily use.

Consider upgrading your Apple Watch when:

  • The battery no longer lasts a full day: Check your battery’s condition on the watch in Settings > Battery > Battery Health. If maximum capacity has dropped below 80% or you’re charging midday to make it to bedtime, the battery has degraded significantly. Battery replacements cost $79–$99 from Apple, but given the watch’s age at that point, upgrading usually makes more sense.
  • Performance feels sluggish: Newer watchOS versions can bog down older hardware. If apps take a long time to launch, Siri responds slowly, or the interface stutters, a newer watch will feel dramatically faster.
  • New health features matter to you: Apple regularly adds meaningful health capabilities. Recent additions like sleep apnea detection may be worth upgrading for.

For most users, a 4–5 year upgrade cycle is reasonable. If you rely on your Apple Watch for health monitoring or use it heavily for workouts, you might prefer a 3–4 year cycle to ensure accurate sensors and reliable battery life.

Other Apple Devices

What about the other items in Apple’s product lineup?

  • Apple TV: Most people can keep an Apple TV for 5–7 years without issue. The only real reason to replace an Apple TV HD or 4K is if performance has become sluggish or you want specific new features like Thread support for smart home devices.
  • AirPods: Battery degradation is unavoidable in devices this small. Most users find that AirPods need replacement after 2–3 years as battery life diminishes. Battery replacement costs $49–$79 from Apple, but the economics and new features usually favor replacement.
  • HomePod: HomePods have long useful lives with little reason to upgrade. Replace a HomePod only if it stops working or if you want features exclusive to newer models, like sound recognition for smoke alarms.
  • AirTags: You can replace the CR2032 batteries in AirTags, so the main reason to replace an AirTag is if it’s lost or physically damaged. Apple released a second-generation AirTag with improved range, but if your current AirTags are working fine, there’s no compelling reason to upgrade.
  • Vision Pro: There’s now an M5-based Vision Pro, but it’s a modest update—if you have the original M2-based model, there’s no reason to upgrade. If you have a Vision Pro, enjoy it—you’re still pretty much on the bleeding edge.

If you’re unsure whether it’s time to upgrade a specific device, we’re happy to help you evaluate your options.

(Featured image generated by Adam Engst with ChatGPT)

Not Sure If You’re Presentable for a Video Call? Try Hand Mirror

Since the pandemic, video calls have become a fact of life for many of us, so much so that it’s now possible to sit down for a meeting without thinking about whether you’ve changed out of your pajamas or brushed your hair. (No judgment; we’ve all done it.) To ensure that you’re presentable before you connect, use the Mac app Hand Mirror. It adds an icon to your menu bar that, when clicked, shows you what your webcam sees. Hand Mirror is free, but you can pay $6.99 for Hand Mirror Plus, which adds features like snapshots, a mic check, quick access to reaction icons, different window types, and more.

(Featured image by iStock.com/Tatsiana Volkava)

How AI Vulnerability Detection Changes Software Security

The latest generation of AI models has fundamentally changed how quickly security vulnerabilities can be found in software, for both defenders and attackers. Understanding what’s happening helps explain why we keep emphasizing the importance of keeping your devices updated.

In April 2026, AI company Anthropic announced Mythos Preview, an AI model with unprecedented capabilities for finding security flaws in software. Unlike previous AI-assisted security tools that often produced false positives and created more work for human evaluators, Mythos proved that it can discover true vulnerabilities that have evaded detection for decades—including a 27-year-old bug in OpenBSD, an operating system famous for its security.

Alongside Mythos, Anthropic launched Project Glasswing, a collaborative effort with approximately 50 partners—including Apple, Microsoft, Google, Amazon, and numerous financial institutions—to identify and fix vulnerabilities in critical software before similar AI-powered capabilities fall into the hands of malicious actors. As Firefox engineers said when reporting on their use of Mythos, “The current moment is a perilous one, but also full of opportunity. Let’s work together to secure the internet.”

Why This Matters

The security implications are significant. Within a month of Project Glasswing’s launch, Anthropic reported that partners collectively found more than 10,000 high- or critical-severity vulnerabilities in their software. Several partners reported that their bug-finding rate increased by more than tenfold.

Firefox developer Mozilla published compelling evidence of Mythos’s capabilities, noting that it identified and fixed 271 vulnerabilities in Firefox 150—over 10 times as many as they found in Firefox 148 with the previous-generation Claude Opus 4.6. Of those 271 bugs, 180 were rated high-severity, meaning they could be exploited through normal user behavior, such as browsing a Web page. (The chart below shows higher numbers because it includes bugs from other sources and other versions.)

Mozilla’s results are remarkable for both their volume and their quality. Firefox engineers reported finding bugs that had remained undiscovered through many years of traditional security testing.

How Apple Fits In

Apple is a founding partner in Project Glasswing, yet another signal that the company takes security seriously. Apple’s vertical integration—controlling everything from chip design to the operating system to the App Store—gives it a structural advantage in secure design. For instance, Apple’s newest M5 Mac chips and A19 iPhone and iPad chips include Memory Integrity Enforcement (MIE), a hardware-level protection designed specifically to stop memory corruption exploits.

However, even these cutting-edge protections aren’t invulnerable. Security researchers at Calif.io demonstrated the first public macOS kernel memory corruption exploit on M5 silicon in May 2026. Working with Mythos Preview, they built a working privilege escalation exploit in just five days—targeting hardware protections that Apple spent five years developing.

An Arms Race Against Time

The uncomfortable reality is that while Anthropic currently controls access to Mythos, equivalent capabilities will inevitably become more widely available. OpenAI and Google probably already have similarly capable models in development, as do other AI model developers, some of whom may be accessible to or even beholden to hostile entities.

The security dynamics differ depending on whether we’re talking about existing software or new code that hasn’t shipped yet. For new code, defenders have a clear advantage—they can scan for vulnerabilities before release and catch bugs that would never have been found manually.

For existing software already running on billions of devices, the picture is darker. Attackers only need to find one exploitable bug to get in; defenders need to find and fix all of them. Worse, attackers don’t have to test their code to avoid breaking features, schedule a release, or get approval from other departments—they can exploit a vulnerability the moment they find it. As the Zero Day Clock site shows, the window between a vulnerability being discovered and being exploited has dropped precipitously—what once took months now happens in days and is expected to happen in minutes in a year or two.

This transition period—while AI rapidly discovers vulnerabilities in existing code that takes time to patch—is where we’re most at risk. The Zero Day Clock site features a call to action offering 10 suggestions for how the industry—and society—should rethink cybersecurity to stave off this threat.

Keep Installing Updates

For most users, the best defense against AI-powered exploits is nothing new—keep your devices updated—but it’s more important than ever. The fixes in Apple’s updates increasingly include patches for AI-discovered vulnerabilities. Practically speaking, you should:

  • Enable automatic updates: Don’t allow yourself to forget to install updates. On iPhones and iPads, go to Settings > General > Software Update > Automatic Updates. On Macs, go to System Settings > General > Software Update, click the ⓘ button, and turn on all the switches. (If you’re working in an organization with an update policy, check with IT first.)
  • Consider security in hardware upgrades: Although the main reason to upgrade hardware should be functional, keep in mind that a newer device will likely be more secure thanks to improved hardware protections.
  • Replace unsupported devices: Hardware that no longer receives security updates is increasingly risky. This applies not just to your Apple devices but to every piece of gear that can be updated, including network hardware, printers, and smart home devices like cameras and doorbells.

In the long run, the emergence of AI-powered security tools favors defenders—developers will be able to catch many more bugs before shipping. For the near future, however, it’s essential that we keep our devices running the latest and most secure software.

(Featured image by iStock.com/Thinkhubstudio)

Office 2019 for Mac Goes Read-Only on July 13, 2026

If you’re still using Microsoft Office 2019 for Mac, on July 13, 2026, an expiring certificate will cause your copies of Word, Excel, PowerPoint, and Outlook to enter “reduced functionality mode,” meaning you can view and print documents but cannot edit or create new ones. To check if you’re affected, open Word and choose Word > About Microsoft Word (or the equivalent in any other Office app). If it says you’re using Office 2019, you need to act before July 13. Some newer versions are also affected but can be updated—for Office 2021 and Microsoft 365, an update is required for app versions under 16.83, and macOS 12 Monterey or later is required. For Office 2019 users, options include subscribing to Microsoft 365 ($99.99/year), purchasing a one-time license for Office 2024 for $179.99 (Home) or $249.99 (Home & Business with Outlook), or switching to alternatives like Apple’s iWork apps (Pages, Numbers, and Keynote), LibreOffice, or Google Docs. New purchases of Microsoft 365 or Office 2024 require macOS 14 Sonoma or later, so users whose Macs can’t upgrade must use Microsoft 365 on the Web, consider the alternatives, or upgrade their hardware.

(Featured image based on an original by iStock.com/grinvalds)