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Make Sure to Back Up iPhone Photos on Your Mac

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If your iPhone were to be stolen or suffer an unfortunate accident, would you lose all your precious photos? Those using iCloud Photos are probably shaking their heads smugly, thinking that all those baby and vacation photos are backed up securely in iCloud. iCloud Photos does indeed store a copy of all your photos, but you shouldn’t assume that everything in it is completely protected. Although it’s extremely unlikely that Apple’s systems would fail so that you’d lose anything, the contents of your iCloud account aren’t as safe as would be ideal.

An Aside to Explain Why iCloud Isn’t Perfectly Secure

Recently, Wall Street Journal reporters Joanna Stern and Nicole Nguyen covered a troubling form of crime aimed at iPhone users in an article (paywalled) and accompanying video. Thieves hang out in bars, looking for users who tap in their passcodes instead of using Face ID or Touch ID. Once they’ve learned someone’s passcode with surreptitious shoulder surfing, they grab the iPhone and run. As soon as they’re clear, they use the passcode to change the user’s Apple ID password and enable or reset a recovery key, which prevents the user from employing Find My to locate and lock the iPhone. Worse, with the passcode, they can make purchases with Apple Pay, access all passwords in iCloud Keychain, and use other information on the iPhone to facilitate identity theft. It’s a disaster.

But it gets worse, as the reporters detail in a new Wall Street Journal article (paywalled) and video. By enabling a recovery key, the thief disables Apple’s normal account recovery process for resetting the Apple ID password. In other words, if this were to happen to you, along with all the financial losses and headaches, you would lose access to your iCloud account, possibly forever, and with it, all your photos in iCloud. With luck, Apple will block this attack soon.

For now, follow this commonsense advice to reduce the chances of being victimized:

  • Pay attention to your iPhone’s physical security in public.
  • Always use Face ID or Touch ID in public.
  • If you must enter your passcode in public, conceal it from anyone nearby.
  • Never share your passcode beyond highly trusted family members.

Backing Up Your iPhone Photos

As with so many other modern ills, good backups go a long way toward minimizing the pain of problems. They won’t prevent someone from stealing your iPhone or locking you out of your account, but if that were to happen, at least you won’t lose all your photos!

There are two possible backup scenarios. Using iCloud Photos and downloading originals to your Mac is easiest but requires that you pay Apple for more storage if you have more than a handful of photos. If you don’t use iCloud Photos, you can just back up your iPhone to your Mac or, better yet, import images into Photos on the Mac and then sync them back. It’s more work and fussier, but doesn’t cost anything.

  • iCloud Photos: When using iCloud Photos, the trick to protecting your pictures is to sync the originals with your Mac. In Photos > Settings/Preferences > iCloud, select Download Originals to this Mac. The only downside of this approach is that you need enough disk space on your Mac to hold them all; if that’s not the case, you may need to move your system Photos Library to an external hard drive.
  • iPhone-only photos: If you aren’t using iCloud Photos, the best approach is to connect your iPhone to your Mac using a USB-to-Lightning cable or Wi-Fi and then import new snapshots into Photos on your Mac manually (select the iPhone in the Photos sidebar). It’s helpful to remove the original photos from the iPhone with the Delete Items checkbox after importing so you can manage them solely on the Mac.

    Then you can sync all the photos (or just desired ones, if your iPhone is low on space) back to your iPhone using the Finder. First, select the iPhone in a Finder window’s sidebar. Then click Photos in the button bar at the top, and select “Sync photos to your device from Photos” along with “All photos and albums” and “Include videos” in the options below. Finally, click Apply or Sync.

    Technically speaking, backing up your iPhone to your Mac without syncing to Photos also backs up your photos, but the only way to get them back is to restore a backup onto an iPhone. It’s much better to have all the photos accessible in Photos too.

Either way, once the photos are on your Mac, you should back up all your data using Time Machine, an Internet service like Backblaze, or a third-party app like Carbon Copy Cloner or SuperDuper. If you’re concerned about the quality of your backups for preserving photos, contact us for advice.

(Featured image by iStock.com/metamorworks)

Social Media: With new reports of iPhone theft victims being locked out of their iCloud accounts, it’s all the more important that you copy your iPhone photos to a Mac and then back up that Mac.

How Often Should Macs Be Replaced?

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It’s a question as old as the personal computer. When should you replace your current Mac with a new model that’s faster and more capable? If money were no object, the answer would be easy—whenever you feel like it. For the rest of us, and particularly for organizations with multiple Macs and limited budgets, the question is harder to answer. But answer it we must because most of us can’t do our jobs without a Mac.

Let’s first look at some of the things that might encourage you to upgrade:

  • Performance and resale value: Many companies and large organizations swap out their Macs every 3 to 5 years. That’s considered the sweet spot where performance starts to decline, but resale value remains relatively high. Plus, Macs of that age start to have more problems that may require repair, resulting in lost productivity due to downtime.
  • Hardware limitations: At some point, you might feel your Mac is too slow—you’re seeing the spinning beachball frequently, or tasks are taking too long to complete. Another common concern crops up when you frequently have to shuffle files around to deal with low disk space on the startup drive. Or perhaps the battery life of a Mac laptop isn’t always sufficient for your needs—losing hours of productivity while on an airplane without seat power can be problematic.
  • macOS support: Although there’s no requirement that you run the latest version of macOS, being unable to upgrade is a hint that your Mac is getting older. Apple provides security updates for the two versions of macOS before the current one, so if your Mac can’t stay within that update circle, it will become more vulnerable to security exploits.
  • Physical damage: Macs are fairly durable, which often keeps them running even when the screen is cracked, a key sticks sometimes, or the case has been dented. The more damage your Mac has, the more likely it is that something else will go wrong, potentially at an inconvenient time.
  • General flakiness: It’s hard to quantify this, but an older Mac might start to feel slow, crash more often, or act weirdly. Sometimes those problems can be resolved by reinstalling macOS and apps from scratch, but that’s a lot of work and far from guaranteed.
  • Repair support: Apple guarantees that it will provide parts and service for all products within 5 years of when Apple last distributed them for sale. After that, Apple considers the products “vintage” for the next 2 years and will repair them subject to parts availability. Apple considers products pulled from the market more than 7 years before to be “obsolete” and won’t repair them apart from Mac laptops that are eligible for an additional battery-only repair period.
  • Shiny new Mac: Sometimes, it’s easy to delay a new Mac purchase because none of the Macs seem quite right. At other times, however, the exact Mac you want will be released just when you need it, making for an easy decision.

With those variables in mind, let us offer recommendations for different audiences:

  • Large-fleet organizations: It’s probably not worth the time to consider the needs of every employee in the context of what Mac they have. Instead, create a policy for replacing Macs on a 3- to-5-year schedule you can build into your annual budget. When it’s time to replace a particular Mac, swap it out for a comparable new model and send the old one to a resale organization.
  • Small-fleet organizations: For companies and nonprofits with a smaller number of Macs and a smaller budget, stick with the same 3- to 5-year schedule, but instead of automatically replacing each Mac as its number comes up, use it as an opportunity to evaluate the user’s needs and then either replace the Mac or set the next evaluation date. You may end up replacing Macs slightly less often, perhaps every 4 to 6 years. It’s also more likely that old Macs will be handed down rather than resold.
  • Creatives and freelancers: If you live and die by the work you can accomplish on your Mac, pay regular attention to whether your Mac is meeting your needs. You’ll probably start to notice issues in 3 to 5 years, and as soon as you do, start watching Apple’s releases to see what new Mac might be the best replacement. Also, consider saving a small amount per month with the idea that you’ll have enough to buy your new Mac about the time the old one noticeably starts to cut into your productivity.
  • Home users: As long as the Mac meets your needs and can run a version of macOS that’s receiving security updates, there’s no harm in continuing to use it for 8 years or more. However, if it starts to need hardware repairs and repeated consultant visits, that’s an indication that you should spend the money on a new Mac instead. Once it can no longer run a supported version of macOS, it’s time for a replacement.
  • Fixed budgets: We get it—sometimes there’s no money for a new Mac. Assuming you can accomplish what you need to do and avoid sketchy parts of the Internet, go ahead and run your current Mac into the ground. It could last 10 years or more. And when it comes time to replace it, there’s no shame in looking to the used market—all those Macs that others are replacing often come up for sale at bargain prices.

We hope this has given you some structure for thinking about replacing Macs, whether you’re worried about the Mac on your desk or all those in the entire design department. And, of course, feel free to contact us for help putting together a replacement schedule.

(Featured image by iStock.com/Prykhodov)

Social Media: When should you replace the Mac on your desk—or your organization’s Macs? There is no single answer, but we run down some variables that play into the decision and make recommendations for different use cases.

You Can Now Upgrade to macOS 13 Ventura When You’re Ready

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When upgrading to a new version of macOS, we err on the side of caution, at least in our recommendations. (We’ve been using macOS 13 Ventura for some time now and often install beta releases on secondary machines for testing purposes.) Upgrading is easy, but if you upgrade too soon, the new macOS version could make key apps inoperable, create workflow interruptions, or cause other negative consequences. On the other hand, waiting too long can cause problems—it’s important to stay in sight of the cutting edge for security reasons and to take advantage of Apple’s advances. Upgrading is not an if question; it’s a when question.

That when could be now. There’s no reason you must upgrade to macOS 13 Ventura right away, but if you want to, you should now be able to do so without undue interruptions. Ventura has been quite stable and has received only three updates since its initial release in October 2022:

  • macOS 13.0.1 provided just unspecified bug fixes and two security fixes.
  • macOS 13.1 introduced the Freeform digital whiteboard app, Advanced Data Protection for iCloud, improved searching for photos in Messages, participant cursors for shared notes in Notes, and the option to play sounds in the Find My app. There were also a couple of bug fixes and important security fixes.
  • macOS 13.2 added support for Security Keys for Apple ID for those who need the utmost security, fixed a few bugs, and blocked more security vulnerabilities.

Apple may have another feature or two up its sleeve for Ventura, and we’ll undoubtedly see more updates to address bugs and newfound security vulnerabilities, but there’s no significant reason to wait any longer.

That said, you can continue to delay as long as you’re running macOS 11 Big Sur or macOS 12 Monterey and are staying up to date with Apple’s security releases. (Both have received important updates recently.) Earlier versions of macOS no longer receive security fixes, rendering them more vulnerable to attack. Reasons to delay include:

  • You’re too busy. The upgrade process will take a few hours, and it may take additional time to configure everything properly afterward. When you are ready to upgrade, aim for when a little downtime will be convenient.
  • You’re still using incompatible software. The jump from Big Sur or Monterey to Ventura isn’t a big one, so most modern apps should have been updated to ensure compatibility with Monterey by now. But if you’re still running macOS 10.14 Mojave or earlier with 32-bit apps, you’ll lose access to them if you upgrade. (That first happened with macOS 10.15 Catalina in 2019.) With Mojave no longer receiving security updates, you need to find replacements for those apps and upgrade soon.
  • You need consistent versions for workflow reasons. We’re unaware of any examples here, but it’s not inconceivable that a coworker could be stuck on an older version of macOS and thus older versions of shared productivity apps. If your upgrade would force you to update those apps and introduce compatibility issues when collaborating with that coworker, you may have to wait until your coworker can upgrade as well.

Ventura won’t upend your experience of using a Mac, but it has numerous useful features, large and small. Along with the features mentioned above that shipped in updates, the new iCloud Shared Photo Library enables you to share photos and videos with up to five family members in a separate shared library. Stage Manager provides a new paradigm for window management. Messages lets you edit messages, undo sending, and mark conversations as unread. Similarly, Mail lets you undo sending, schedule messages to send later, and get follow-up reminders for replying. For better videoconferencing quality, Continuity Camera enables you to use your iPhone as a webcam, complete with Desk View for showing what’s on your desk during a call. The Mac finally gets its own Weather app. Perhaps even more important, Ventura shares some of these features with Apple’s other operating systems: iOS 16, iPadOS 16, watchOS 9, and tvOS 16. To take full advantage of those features across all your Apple devices, your Mac must be running Ventura.

However, we want to be upfront about one downside to upgrading to Ventura. Apple replaced System Preferences with System Settings. While we wouldn’t have described System Preferences as having a stellar user interface, it was at least familiar after decades of use. The new System Settings, which tries to mimic the Settings app in iOS and iPadOS, moves numerous settings around and makes some odd and unfortunate design decisions. You may find yourself relying heavily on its search field to find commonly used options.

Before You Upgrade

Once you’ve decided to upgrade to Ventura, you have three main tasks:

  • Update apps: Make sure all your apps are as up-to-date as possible. If you regularly put off updates, now’s the time to let them complete so you have Ventura-compatible versions.
  • Clear space: Ventura needs about 25 GB of free space to upgrade, and the Ventura installer itself is about 12 GB, so we recommend making sure you have at least 37 GB free. Don’t cut this close—you should always have at least 10–20% free space for virtual memory, cache files, and breathing room. Check by choosing About This Mac from the Apple menu and then clicking Storage.
  • Make a backup: Never, ever install an update to macOS without ensuring that you have at least one current backup first. In an ideal world, you’d have an updated Time Machine backup, a bootable duplicate, and an Internet backup. That way, if something goes wrong, you can easily restore.

Upgrading

After completing the above-listed tasks, ensure you don’t need your Mac for a few hours. There’s no telling exactly how long the upgrade will take, so never start an upgrade if you need the Mac soon.

Initiating the upgrade is just a matter of opening System Preferences > Software Update, clicking the Upgrade Now button, and following the instructions. If you’d like more handholding, check out Joe Kissell’s ebook Take Control of Ventura.

After You Upgrade

Part of the reason to set aside plenty of time for your Ventura upgrade is that there are usually cleanup tasks afterward. We can’t predict precisely what you’ll run into, depending on what version of macOS you’re running now and what apps you use, but here are a few situations we’ve noticed in the past:

  • macOS may need to update its authentication situation by asking for your Apple ID password, your Mac’s password, and if you have another Mac, its password too. Don’t worry that your Mac has been compromised by malware—it’s fine.
  • Some apps may have to ask for various permissions even though you previously granted them. Again, that’s fine and won’t happen again.
  • If you use your Apple Watch to unlock your Mac and apps (and you should, it’s great!), you may need to re-enable that in System Settings > Touch ID & Password (it’s an example of something that moved; previously, it was in System Preferences > Security & Privacy > General).
  • If you use Gmail, Google Calendar, or other Google services, you may need to log in to your Google account again.
  • Websites that usually remember your login state may require that you log in again. If you’re using a password manager like 1Password, that’s easy.
  • You may have to re-enable text message forwarding to your Mac. You do this on your iPhone in Settings > Messages > Text Message Forwarding.

With all that housekeeping done, it’s time to check out all the new features in Ventura!

(Featured image by Apple)

Social Media: Should you upgrade to macOS 13 Ventura? There’s no need to install it today, but we think it’s now safe for those who want to take advantage of the new features and integration with Apple’s other operating systems. Details here:

Apple Is Driving the iPhone to eSIM: Here’s What You Need to Know

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Perhaps the most surprising change in the iPhone 14 line, at least in the United States, was the shift from using removable SIM cards to eSIM.

SIM cards—SIM stands for Subscriber Identity Module—have been a fixture in the mobile phone world for many years because they provide the unique identification necessary to connect a subscriber and a plan with a phone. Because SIM cards are removable, you can use them to transfer an existing plan to a new phone, switch carriers, or enable temporary service while traveling—all by inserting the appropriate SIM card.

But SIM cards are small, fussy, and require physical interaction, so the industry came up with eSIM, or embedded SIM, where a programmable SIM is integrated into the circuitry of the phone. With eSIM, you can also activate a plan, transfer a plan to a new phone, or change carriers, typically without interacting with customer service. You also don’t have to acquire a physical SIM, figure out how to open your phone’s SIM tray, or insert the tiny SIM card in the correct orientation without dropping or damaging it. Plus, without a SIM slot and tray, iPhones have one less spot where water could get in and one less moving part that could break, and Apple doesn’t have to provide a SIM tool that you’ll likely lose (and replace with a paperclip).

Apple’s eSIM Transition

eSIM support is widespread among US carriers but less so internationally, which is why models of the iPhone 14 sold outside the US retain the SIM tray. The main place where lack of eSIM support is likely to be an issue—at least for the near future—is international travel. Historically, it was easy to purchase a pre-paid SIM card for a local carrier in the airport upon arriving, but that will no longer work for a US iPhone 14. The iPhone is sufficiently popular that international carriers are adding eSIM support, but it’s still possible to travel to a country where you can’t get local service with an iPhone 14 due to the lack of a SIM tray. Apple maintains a list of international carriers that support eSIM in various ways, including with pre-paid plans for travelers, and offers advice on how to use eSIM when traveling. (eSIM isn’t available at all in mainland China, but Apple’s list includes worldwide service providers that sell pre-paid data plans you can use when traveling in China and other countries without eSIM support.)

Apple has been moving toward eSIM for several years, starting with the iPhone XS, iPhone XS Max, and iPhone XR in 2018. Those iPhones—and every model up to the iPhone 14—had both a SIM tray and eSIM, which enabled the use of two separate cellular plans, each with its own phone number. With the iPhone 13, Apple enabled Dual SIM support with eSIM alone, and some carriers started giving customers the option to activate their primary service with eSIM, leaving the SIM tray or the second eSIM available for a second plan. Apple says you can store and switch among up to eight or more eSIMs, two of which can be active at any time, but it’s unclear how that works—an update to iOS might be necessary.

Cellular-capable iPads have had eSIM support since the seventh-generation iPad, fifth-generation iPad mini, third-generation iPad Air, first-generation 11-inch iPad Pro, and third-generation 12.9-inch iPad Pro.

How to Activate an eSIM

Precisely how you activate an account with eSIM varies by carrier and your situation, but Apple describes three basic options:

  • eSIM Carrier Activation: Some carriers can assign a new eSIM to your iPhone, making it easy to switch to a new iPhone or enable an eSIM-based plan after setup. eSIM Carrier Activation involves following a few simple onscreen instructions where you basically acknowledge that activation is happening. Make sure you can place a phone call afterward, and if you’re switching from a SIM card, remove it and restart your iPhone.
  • eSIM Quick Transfer: If you’re transferring a SIM or eSIM from an old iPhone to a new one and you have both at hand, you may be able to use eSIM Quick Transfer. It will provide instructions during setup, or you can initiate it after setup with Settings > Cellular > Add Cellular Plan and either selecting a plan from a list or tapping Transfer From Another Device. You can also convert a physical SIM to an eSIM on the same phone if your carrier supports eSIM Quick Transfer; check to see if Settings > Cellular has a Convert to eSIM option. If so, tap it and follow the instructions.
  • Scan a QR code or use a carrier app: Carriers that don’t support eSIM Carrier Activation or eSIM Quick Transfer initiate setup by providing either a QR code you can scan—during setup or afterward—or a custom app. Either way, follow the iPhone’s instructions to complete the setup.

Although we’ve become accustomed to swapping SIM cards in and out of our iPhones such that eSIM feels new and confusing, it should be a better overall solution that’s easier to set up, less error-prone, and more secure. There may be some short-term annoyance for US iPhone 14 owners who travel internationally, but we anticipate that will dissipate over time as international carriers start supporting eSIM.

(Featured image by iStock.com/fz750)

Social Media: Apple has gone all-in on eSIM, eliminating the SIM tray from iPhone 14 models sold in the US. What’s eSIM? Glad you asked—read on for the details of the technology and why it’s better than SIM cards.

When Should You Upgrade to macOS 13 Ventura, iOS 16, iPadOS 16, watchOS 9, and tvOS 16?

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September is here, which means that Apple will soon start releasing major upgrades for all its operating systems. Note that we say “start.” Apple will release iOS 16 and watchOS 9 alongside new iPhones and Apple Watch models in September. However, Apple has now acknowledged that iPadOS 16 will ship later in the fall—perhaps in October—as version 16.1, likely in conjunction with iOS 16.1 and possibly alongside macOS 13 Ventura. tvOS 16 isn’t interesting enough to worry about much either way.

Apple previewed these releases at its Worldwide Developers Conference in June, and many people have been testing the public betas since. Once Apple judges each of its operating systems to be ready for public consumption, the question arises—when should you upgrade?

Note that we say when and not if. There’s no harm in delaying a major operating system upgrade until Apple has sanded off rough edges that slipped through testing. But waiting too long puts you at risk from security vulnerabilities, increases compatibility annoyances, and prevents you from taking advantage of new features. Plus, when you buy a new Mac, iPhone, or iPad after these operating systems have shipped, you’ll get the latest version, which could pose problems for your existing apps or compatibility with older hardware or workflows. It’s best to be prepared if you have to replace a device unexpectedly.

Given that we don’t know precisely when each operating system will come out, here’s our recommendation for the general upgrade order that we anticipate and how long we suggest waiting after the release appears. Remember, always make a backup before upgrading a Mac, iPhone, or iPad so you can revert if necessary.

iOS 16

It’s usually safe to upgrade iOS fairly quickly because Apple puts significant effort into ensuring that the new iOS version is a good experience for those who buy the new iPhones that come with it. However, because iPhones are so crucial to our everyday lives, it’s worth delaying the upgrade to iOS 16 for a few weeks, just in case. After that, you can install it and enjoy the new features.

You’ll likely enjoy iOS 16’s customizable Lock screen, which lets you specify the font, color, and placement of various options, all of which appear with photos that can shuffle throughout the day. Widgets can now appear on the Lock screen too, providing at-a-glance weather and other info even without unlocking your iPhone. The new dictation capabilities that let you talk, select, and type without switching modes may also be game-changing for some, and dictation will even add punctuation automatically and let you enter emojis with voice commands.

However, some features may not be fully available at the start due to Apple’s tight integration of operating systems. Messages will finally let you edit messages after sending, undo sending, and mark messages as unread—but editing and unsending won’t work for messages sent to people running anything earlier than iOS 16, iPadOS 16, and Ventura. We’re unsure if Apple will enable iCloud Shared Photo Library, which lets you automatically share an entire library of photos with family members or friends, until iPadOS 16 and Ventura are out as well. Similarly, the Continuity Camera feature of iOS 16, which lets you use your iPhone as a webcam for your Mac’s videoconferencing apps, won’t be available until Ventura ships.

watchOS 9

Once you upgrade your iPhone to iOS 16, there’s no reason to delay upgrading your Apple Watch to watchOS 9. You may not even notice the difference since none of the changes are likely to force changes in your usage patterns.

New features include new views and more metrics in the Workout app, including a display of heart rate zones and pace feedback. You can customize workout and recovery intervals, race against previous routes, get running form metrics, and see your running power. Also new is a Medications app that helps you remember to take medications and log them from reminders. And, of course, there are more watch faces.

tvOS 16

We don’t know when Apple will release tvOS 16, but the changes are so minimal that it doesn’t matter much. tvOS 16 will support more Bluetooth gaming controllers, provide full support of the Matter smart home standard, and offer more integration with your other Apple devices, such as with workouts in Apple Fitness+.

Unless something in that list encourages you to upgrade as soon as it’s out, we suggest letting your Apple TV (the fourth-generation model and later) upgrade itself when it gets around to it, assuming you have automatic updates turned on in Settings > Software Updates.

iPadOS 16

iPadOS 16 may not be available until October, but once it ships, our general advice is that it’s fine to update. For the most part, iPadOS is a superset of iOS, so if anything, Apple should have had some time to fix any early bugs that cropped up in iOS 16 before releasing iPadOS 16.

The big new feature in iPadOS 16—if you have an M1-equipped iPad like the latest iPad Air or iPad Pro—is Stage Manager, which brings a structured windowing system to the iPad and Mac. Stage Manager lets you stack up to four apps in an overlapping view, providing additional sets of apps off to the side in a sort of secondary Dock. If you connect your iPad to an external display (along with a keyboard and pointing device), it offers another separate workspace, so you can work more fluidly in multiple apps at once.

If you want to see more on screen, a new display scaling mode shrinks interface elements and content. It may make Stage Manager and Split View more helpful. You’ll also likely enjoy a better search in Mail, plus options to undo sending, schedule sending, follow up on sent messages, and add rich links. (These Mail features are shared with iOS 16 and Ventura.) Last but not least, the iPad finally gets its own Weather app.

macOS 13 Ventura

The hardest upgrade decision revolves around upgrading your Mac to macOS 13 Ventura, and that assumes you can upgrade at all, given that Apple has dropped support for all Macs released before 2017. The main new feature that you might find compelling is Stage Manager, although most longtime Mac users probably already feel comfortable with their window management skills. If you spend a lot of time in video calls, the new Continuity Camera feature that lets you use your iPhone (running iOS 16, natch) as a high-quality webcam with support for Center Stage—which enables the camera to follow you as you move around—may also be attractive. And, of course, you’ll get the new Messages, Mail, and iCloud Shared Photo Library features that Apple added to iOS 16 and iPadOS 16.

We always encourage caution when upgrading to a new version of macOS. Wait at least a few months before upgrading your primary Mac to Ventura. App compatibility isn’t usually a long-term problem with iOS and iPadOS, but many people rely on older Mac apps that may not work in the latest version of macOS. Even once you’re confident that your apps will work properly in Ventura, there may be workflow or intra-office compatibility concerns if some people upgrade and others don’t. And, of course, unanticipated bugs could crop up at inconvenient times—important work takes place on Macs! Please, do not upgrade to Ventura without checking with us first. With luck, the start of the new year will have brought both the bug fixes and app updates necessary to give the green light.

(Featured image by Apple)

Social Media: Apple is gearing up to release macOS 13 Ventura, iOS 16, iPadOS 16, watchOS 9, and tvOS 16. We take a brief look at the features worth upgrading for and suggest when to upgrade each of your Apple devices.

The Best Characters to Use When Naming Files and Folders

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Back in the early 1980s, DOS filenames couldn’t be more than 8 characters long with a period and a 3-character extension. That was limiting, so when Apple developed the Mac operating system in 1984, it allowed longer names and eliminated the need for an extension, although Mac OS X’s Unix roots meant a return of the filename extension in 2001. Since then, filename restrictions have loosened to the point where it’s easy to think that they no longer exist.

If only that were true! In some ways, the situation has become even cloudier, thanks to additional limitations from file-sharing services like Dropbox, OneDrive, and Box. (Google Drive’s native Web interface reportedly has no naming limitations, but files whose names contain Windows or macOS forbidden characters may not sync via Google Drive’s desktop software.) Plus, people tend to move files between operating systems more than ever before—if you’re sending a file from your Mac to a Windows user through Dropbox, you need to make sure that all three can deal with the filename.

At least length isn’t something that you generally have to think about these days, since both macOS and Windows—and the cloud services—accept filenames up to 255 characters in length. Technically speaking, Windows limits directory paths (the enclosing folder names along with the filename) to 255 characters, but even still, that shouldn’t be difficult to avoid.

What could go wrong if you run afoul of a naming restriction? macOS and Windows may simply not let you type the character—for example, you can’t put a colon in a Mac filename. Putting a period at the start of a Mac or Unix filename will hide the file. Cloud sharing services might rename the file, or you might encounter syncing issues where files don’t appear where they should. Certain characters can also cause trouble when files are used at the command line.

Here are the characters to avoid and the operating systems and services that prohibit them:

  • : (colon): macOS, Windows, Dropbox, OneDrive, Box
  • . (period): macOS (at the start of a name), Dropbox
  • / (forward slash): macOS, Windows, Dropbox, OneDrive, Box
  • (backslash): Windows, Dropbox, OneDrive, Box
  • < (less than): Windows, Dropbox, OneDrive, Box
  • > (greater than): Windows, Dropbox, OneDrive, Box
  • ” (double quote): Windows, Dropbox, OneDrive, Box
  • | (vertical bar or pipe): Windows, Dropbox, OneDrive, Box
  • ? (question mark): Windows, Dropbox, OneDrive, Box
  • * (asterisk): Windows, Dropbox, OneDrive, Box
  • ^ (caret): Windows (using FAT-formatted drives)

In addition, avoid using special characters like the © (copyright) symbol or emoji 🤷🏽‍♂️  in filenames. They might work locally, but all bets are off if you share the files in any way.

A few other recommendations:

  • Avoid unusual punctuation; in particular, note that OneDrive renames filenames containing:
    • , (comma) to ^J
    • # (number sign) to ^N
    • & (ampersand) to ^O
    • ~ (tilde) to ^F
  • Never start or end file or folder names with a space, and avoid spaces in filenames that will be uploaded to a Web or SFTP server.
  • Avoid putting more than one period in a filename, and don’t put a period after a filename extension.
  • Never assume that names are case sensitive—always make sure that similarly named items differ by more than just case.

If all that seems like a lot to keep in mind, here’s the simple rule that will ensure your filenames will work everywhere:

Name files only with uppercase (A-Z) and lowercase (a-z) letters, digits (0-9), and the hyphen (-) and underscore (_), plus a single period (.) and extension.

(Featured image by iStock.com/cosmin4000 and smartstock)

Social Media: You might think that you can name a file or folder any way you want, but macOS and Windows have restrictions on which characters you can use, and the prevalence of cloud sharing services makes it all the more important to avoid prohibited characters.

Understanding What “Vintage” and “Obsolete” Mean for Apple Products

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Macs—and Apple products in general—tend to last a long time. It’s not unusual to see someone happily using an 8-year-old MacBook Pro. As much as it’s environmentally responsible to use electronics as long as possible, doing so may reduce your productivity or leave your business in a precarious situation if a hardware failure forces an upgrade at an inconvenient time.

Another factor to consider is whether or not you can get service and parts for your older device. It’s easy to assume that Apple will fix whatever you bring in, but unfortunately, that’s not the case. Apple has policies surrounding how long it guarantees to provide service and parts, which is reasonable. No one would expect Apple to repair a 128K Mac from 1984—many repair techs hadn’t even been born then.

All Apple products fall into one of three categories: current, vintage, and obsolete. Current products, which Apple defines as those that were sold within the last 5 years, are eligible for service and parts from Apple, Apple Authorized Service Providers, and Independent Repair Providers. In other words, if you bought your Mac new within the last 5 years, you won’t have any problem getting Apple to fix it.

(Independent Repair Providers are firms that have signed up for Apple’s Independent Repair Provider Program to provide out-of-warranty iPhone and Mac repairs using Apple-provided parts, tools, service guides, and diagnostics. Other repair shops can repair Apple products but may lack Apple certifications and have to source parts from other suppliers.)

Things get trickier with the other two categories:

  • Vintage: Apple considers a product to be vintage when the company stopped selling it more than 5 and less than 7 years ago. During this 2-year window, Apple says that service and parts may be obtained, subject to parts availability.
  • Obsolete: As you’d expect, a product is considered obsolete when Apple hasn’t sold it for more than 7 years. Apple will not service obsolete products, and service providers cannot order parts for them.

There is one exception to these policies. Mac laptops may be eligible for an extended battery-only repair period for up to 10 years from when the product was last distributed for sale, subject to parts availability. That makes sense since a new battery may be all an old MacBook needs to keep working.

Apple maintains a page listing all vintage and obsolete products. To determine which Mac model you have, choose About This Mac from the Apple menu. For iPhones, iPads, and iPods, Apple provides pages explaining how to identify your model.

Apple’s policies surrounding vintage and obsolete products shouldn’t make a huge difference to most users. That’s because once a Mac hits 5 years old, it’s likely that upgrading to a new model will provide significant benefits. Many businesses prefer a 3-year replacement cycle because they’ve determined that’s the sweet spot where increasing support costs and lower performance make it worth selling the old Mac and buying a new one that’s faster and more reliable.

Of course, there’s nothing wrong with keeping a Mac longer if it meets your needs and you don’t mind spending more on support. At some point, though, products in the vintage and obsolete categories are living on borrowed time.

(Featured image by iStock.com/Soulmemoria)

Social Media: It might be easier to repair vintage jeans than a vintage Mac. Read on if you want to understand Apple’s definitions of vintage and obsolete hardware and what they mean for support and repair.

Apple Works to Improve Safety in the Wake of AirTag Stalking Reports

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Over the past few months, there has been a spate of media reports about how people may have been tracked without their knowledge using AirTags, Apple’s elegant location trackers. Like many mainstream media forays into the tech world, the reports are often short on detail and sometimes unclear on the reality of how the AirTags work. Nor is it clear that there have been many successful cases of AirTag abuse, but the mere fact that people are trying to use AirTags to stalk others is concerning.

Apple put significant effort into preventing such abuses, revolving around three features:

  • Safety alerts: If you have an iPhone or iPad running iOS 14.5 or later and an unknown AirTag is traveling with you, your device will alert you to that fact. Although safety alerts aren’t available for those using Android smartphones, Android users can download Apple’s Tracker Detect app to scan manually.
  • Safety sounds: After an AirTag has been separated from its owner for several days, it will make a sound the next time it moves.
  • NFC identification: If you find an AirTag, you can hold it up to an iPhone or other NFC-capable smartphone to load a website that reveals the AirTag’s serial number and the last four digits of the owner’s phone number. The police can use this information to learn the owner’s identity from Apple.

Sadly, those precautions haven’t been sufficient either to dissuade all would-be stalkers or to educate potential stalking victims (and let’s be real—dissuading stalkers is also a matter of educating people that it’s unethical, likely dangerous, and often illegal to abuse an AirTag in this way). Apple has responded in two ways, one general, the other specific to AirTags.

Personal Safety User Guide

Apple documents its products and services quite well, but the company tends to generate many focused pages without much high-level organization. It’s all too easy to flail around within Apple’s support documentation looking for help if you don’t know what search terms are likely to work. In an effort to mitigate that problem for issues surrounding personal safety, Apple has created the Personal Safety User Guide website, also available as a downloadable 56-page PDF.

The Personal Safety User Guide brings together numerous Apple support articles in two main sections:

  • Review and take action: The first section helps you review how your devices and apps are set up, with a focus on settings that could expose you to harm. It helps you manage sharing settings, look at location sharing, control your Home accessories, and more. You’ll also learn how to block unknown sign-in attempts, document suspicious activity, delete suspicious content, and avoid fraudulent requests to share information, among much else. The main criticism here is that the section on AirTag safety doesn’t explain or link to all the features Apple provides.
  • Safety and privacy tools: The second section is a bit more generic, providing support documentation that encourages you to take advantage of the features Apple has provided to protect your safety and privacy. Among other topics, it discusses passcodes, setting up Face ID and Touch ID, using two-factor authentication, seeing which apps are accessing your data, blocking unwanted calls and messages, and using Emergency SOS.

The Personal Safety Guide ends with three checklists, each of which walks you through a series of steps. These are extremely useful because almost no one would necessarily know or remember all the places to check. The checklists help you:

  • See who has access to your device or accounts
  • Stop sharing with someone
  • Control how someone else can see your location

The Personal Safety User Guide website is best when you want an answer to a specific question, but it doesn’t lend itself to reading front to back. For that, we recommend downloading the PDF, which you can read at whatever depth you desire. But do at least scan the entire thing to get a sense of what it contains should you need that information later.

Apple AirTag Announcement

Shortly after releasing the Personal Safety Guide, Apple also posted a short but detailed statement on its website. In it, the company makes it clear that it is actively working with law enforcement on all cases involving AirTag abuse. Apple also says that it has updated its unwanted tracking documentation to explain AirTag safety features more clearly to users and to include resources for those who feel their safety is at risk.

Apple also outlined important advancements that will be coming to the AirTag and Find My network systems via software updates later this year:

  • New privacy warnings during AirTag setup: To ensure that everyone understands the utility of AirTags and the implications of abuse, people setting up an AirTag for the first time will see a message that clearly states that AirTags are meant to track their own belongings, that tracking people without their consent is a crime in many places, that AirTags are designed to alert victims to their presence, and that law enforcement can request identifying information about the owner of an AirTag.
  • Better alerts for AirPods: Instead of an “Unknown Accessory Detected” alert when your iPhone detects Find My network-compatible AirPods traveling with you, the alert will specify that AirPods are involved, not an AirTag. (There are third-party Find My network accessories that will still generate this alert, such as the Chipolo ONE Spot.)
  • Refined unwanted tracking logic: Apple will be updating its unwanted tracking alert system to notify users sooner that an unknown AirTag or Find My network accessory is traveling with them.
  • Precision Finding for unknown AirTags: Those with an iPhone 11, iPhone 12, or iPhone 13 will be able to take advantage of Find My’s Precision Finding feature to home in on the location of an unknown AirTag. Previously, this capability was limited to your own AirTags.
  • Display alerts with unknown AirTag sound: When an unknown AirTag emits a sound to alert anyone nearby to its presence, and it’s detected moving with your iPhone or iPad, an alert will also appear to help you play the sound again or use Precision Finding, if available. This should help when an unknown AirTag is in a place that blocks sound or if its speaker has been disabled.
  • More obvious AirTag alert sound: Apple will be adjusting the tone sequences to make an unknown AirTag’s alert sound easier to hear and find.

Overall, these changes are welcome, and it’s a testament to the care Apple took when designing the AirTag and Find My network systems that it can make such enhancements through software updates—no hardware changes are necessary. It’s also good to see Apple taking the problem—however small it might actually be—seriously and working to reduce it even further.

(Featured image by Apple)

Social Media: Media reports suggest that miscreants are trying to use Apple’s AirTag location trackers to stalk people. Apple has responded with personal safety advice and promised AirTag safety enhancements.

Avoid Unusual Top-Level Domains in Custom Domain Names

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Remember the heady dotcom days, when businesses were desperate to get a short, memorable, easily typed .com domain? It quickly became difficult to get what you wanted—so much so that deep-pocketed companies paid exorbitant sums for just the right domain.

Before we go any further, let’s make sure we’re all on the same page. Domain names are necessary because computers on the Internet are all identified by inscrutable numeric IP addresses. You can remember and type apple.com easily; 184.31.17.21 not so much. Domain names have two or more parts: the top-level domain (read from the end, such as com) and the second-level domain (like apple), plus optional third-level domains (which could give you support.apple.com).

Since the days of speculating in .com domains, however, hundreds of additional top-level domains have been opened up, including domains from .aaa to .zone. There are now top-level domains for .doctor, .florist, .lawyer, and many more, including the general .xyz. It might be tempting to switch from the awkward dewey-cheatham-howe.com to the shorter and more memorable dch.lawyer. And even if there isn’t a profession-specific top-level domain that works for you, you may think that if abc.xyz is good enough for Google’s parent company Alphabet, surely it’s good enough for you.

Alas, much as we appreciate the creativity and flexibility offered by these alternative top-level domains, we’d like to dissuade you from using one, if possible. Problems include:

  • Email deliverability: If you’re sending email using an alternative top-level domain or including links to that domain, it’s much more likely that your email will be considered spam by receiving systems.
  • SMS deliverability: Some SMS text message providers will automatically delete messages containing URLs with alternative top-level domains in an effort to protect their customers from phishing attacks.
  • Social media spam filtering: As with SMS text messages, social media posts that include URLs with alternative top-level domains may be categorized as spam or as linking to a malicious site.
  • Firewall blocking: Abuse of alternative top-level domains has become so commonplace by scammers that some companies prevent their employees from accessing websites using certain alternative top-level domains at the firewall level.
  • User perception: Although there’s no telling how anyone will react to a particular top-level domain, people won’t think twice about .com but might think .ooo seems sketchy. (We would.)

Obviously, it may not be possible to get the domain name you want in .com. What to do? There are a few strategies:

  • Expand or abbreviate: At this time, people mostly don’t see, remember, or type domains apart from those that go with businesses that do a lot of real-world advertising. So if you need to add or subtract words (or letters) in your domain to find a unique one, that can work.
  • Use a country domain: Two-letter top-level domains are restricted for use by countries, so .us is for the United States, .ca for Canada, and .au for Australia. Every country has different rules for who can register them. For instance, it’s possible to get a domain ending in .it (Italy) as long as you work through a registrar that acts as your representative there. .io (British Indian Ocean Territory) and .ai (Anguilla) are popular top-level domains among tech companies.
  • Stick with better, pricier alternatives: Not all alternative top-level domains are equally problematic. The classic .net and .org are fine, and .biz isn’t bad. But how to determine that? When you’re checking to see if a domain name is available, compare prices. For instance, at one domain name registrar, iphonewhisperer.xyz costs only $1 per year, whereas the iphonewhisperer.biz version is $4.98 per year, iphonewhisperer.net is $9.18 per year, and iphonewhisperer.studio is $11.98 per year. The more you pay, the less likely that domain has been abused by spammers and marked for filtering.

In the end, when it comes to domain names, it’s best to be conservative and stick with a top-level domain that won’t cause people or filters to think twice. That’s probably .com, if you can make the rest of the name work for you.

(Featured image by iStock.com/BeeBright)

Social Media: Tempted to get a short, memorable domain name ending in .xyz or .shop? As we explain, that’s a bad idea if you care about user perception, email and text message deliverability, and not being blocked by social media and firewalls. Details at:

New Features to Try (Or Not) in Safari 15

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Along with a new version of Safari in iOS 15 and iPadOS 15, Apple has released Safari 15 for macOS 11 Big Sur and macOS 10.15 Catalina. Why do this before macOS 12 Monterey ships? Some of the browser’s new capabilities—notably the Tab Groups feature—integrate it more deeply into your Apple device experience by syncing across devices. So, assuming you have Safari 15 on at least some of your devices, what’s new, and is it any good?

New Tab Bar Interface

For Safari 15, Apple tried to minimize the tab bar interface to occupy less screen real estate and stand out less from the content of Web pages by co-opting the color of each page. Early betas were met with a litany of complaints from testers, and Apple pulled back in the eventual releases, offering settings that let you retain the old interface. How that plays out varies between the iPhone, iPad, and Mac:

  • iPhone: Apple combined the address bar and tab bar into a single set of controls at the bottom of the screen, where they’re easier to reach with your thumb while working one-handed and where you can swipe left and right to switch tabs. Plus, the status bar area at the top of the screen takes on the color from the current site, which isn’t necessarily a visual win. This is a huge change from the controls appearing at the top, so if you don’t like it, go to Settings > Safari and switch from Tab Bar (below left) to Single Tab (below right). Turn off Allow Website Tinting (also below right) if you don’t like the colorizing.
  • iPad: Displays on the iPad are relatively small, so saving some vertical space with the new Compact Tab Bar could be helpful. However, since the tab bar automatically minimizes when you scroll down a page, reducing its size when it’s visible isn’t as much of a win as it might seem. And the colorized tab bar can be shockingly bright. In Settings > Safari, you can choose between Compact Tab Bar (below top) and Separate Tab Bar (below bottom); either way, consider disabling Show Color in Tab Bar.
  • Mac: Laptop screens aren’t huge, and Safari doesn’t minimize its tab bar when you scroll, as it does on the iPhone and iPad, so saving some vertical space might be welcome on a smaller screen. But the way the Compact layout embeds the address field inside a tab and reduces the number of buttons you can see may perturb you (below top). Once again, the colorized tab bar can be glaring. To revert to something closer to the old look, in Safari > Preferences > Tabs, select Separate for the tab layout (below bottom), and disable Show Color in Tab Bar to keep the controls gray regardless of the site color.

Voice Search

For many searches, it’s easier to speak than type, and Apple has made doing that even faster with Voice Search on the iPhone and iPad. Tap the current tab to display the address field, tap the microphone button, and speak instead of typing. As soon as you stop, Safari performs the search. You can even navigate directly to a site by speaking its URL, like “apple dot com.” Sadly, Apple didn’t extend this feature to the Mac version of Safari 15.

Tab Switcher

In iOS 14 and earlier, Safari used a card stack metaphor for its tab switcher (below left), which could make it hard to see what each tab contained. In Safari in iOS 15, Apple took a cue from the iPad and Mac versions of the app and moved to a grid interface for the tab switcher (below right). You can drag the tab thumbnails around to organize them and remove them by tapping an X button (weirdly located in the upper-right corner) or swiping them left off-screen. You can also bring up the option to close all open tabs by pressing and holding Done at the lower right corner of the screen.

Tab Groups

If you struggle under the cognitive load of dozens of unrelated tabs, the new Tab Groups feature might help. With it, you can collect tabs into as many groups as you like and switch among them. You work with tab groups in either the tab switcher interface (iPhone and iPad with the Separate Tab Bar) or the sidebar (Mac and iPad with the Compact Tab Bar).

To open the tab switcher on the iPhone, tap the tab button in the lower-right corner of the screen; on the iPad, tap the different-looking tab button in the upper-right corner. Once you have the tab switcher open, tap X Tabs to reveal the Tab Groups menu. To show the sidebar on either the iPad or the Mac, tap or click the sidebar button in the upper-left corner of the tab bar.

Once you have the Tab Groups menu or sidebar showing:

  • To create a new tab group on the iPhone’s or iPad’s Tab Groups menu, tap New Empty Tab Group, name it, and tap Save. In the sidebar on a Mac or iPad, use the New Tab Group button at the top (or choose File > New Empty Tab Group on the Mac). You can also use New Tab Group from X Tabs to create a tab group from currently open tabs.
  • To switch to a different tab group, tap it in the Tab Groups menu on an iPhone or iPad, or access it from the sidebar on a Mac or iPad.
  • To delete a tab group, swipe left on it in the Tab Groups menu or sidebar to reveal a delete icon on an iPhone or iPad; on the Mac, Control-click it and choose Delete.

Shared with You

Ever gone spelunking through Messages to find a link someone sent you? Safari 15’s new Shared with You feature should help. It automatically collects all Web pages you receive in Messages into a new Shared with You section of the Safari start page. On the iPad and Mac, there’s also a Shared with You item in the sidebar.

Customizable Start Page

Speaking of the start page, if you want to customize which headings appear and in what order, you can now do that on the iPhone and iPad. (Choosing which headings appear has long been possible on the Mac by clicking the little settings button in the lower-right corner, but reordering isn’t possible there.)

Create a new tab to view the start page, scroll to the bottom, and tap Edit. Then disable any headings you don’t want to see and drag the remaining ones into your desired order. You can also choose among several Apple-provided background images and have your start page settings sync to your other devices.

Other Stuff

Two final new features may be welcome but probably won’t rock your world:

  • Pull to refresh: If you need to reload a Web page on the iPhone or iPad, either you can tap the reload button in the address field if it’s visible with your tab bar settings, or you can now just pull down with your finger from the top of a page.
  • HTTPS upgrade: If you visit a website that supports encrypted HTTPS but is also loading insecure content over unencrypted HTTP, Safari will now ensure that you connect to it over HTTPS so your entire connection is secure.

There you have it! Check out the new features in Safari 15 and let them improve your browsing experience.

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

Social Media: Safari 15 brings some welcome new features, along with tab bar interface changes that have received mixed reviews. Read on to learn about the features and how you can customize the tab bar more to your liking.