The first set of Apple Intelligence features appeared in macOS, iOS, and iPadOS in October. Apple has now debuted the second set in the December releases of macOS 15.2 Sequoia, iOS 18.2, and iPadOS 18.2. Apple still considers them to be in beta, which is a nice way of saying that they may not work perfectly. However, they usually do what they promise.

Remember, Apple Intelligence features work only on a Mac with Apple silicon, an iPad with an A17 Pro or M-series chip, or an iPhone 15 Pro or any iPhone 16. Intel-based Macs and older iPhones and iPads can’t play. If you’ve been holding off on upgrading, this is a fine time to make the jump. Regardless, you must turn on Apple Intelligence, which you do on the Mac in System Settings > Apple Intelligence & Siri and in Settings > Apple Intelligence & Siri on the iPhone and iPad.

What can you look forward to with this second set of Apple Intelligence features?

Image Playground Helps Make Fun Images

With Image Playground, Apple is dipping its toe into AI-driven image generation. The standalone Image Playground app lets you create amusing images with text descriptions, either starting from scratch or from a photo. You can choose from two styles: Animation, which Apple describes as “a modern 3-D animated look,” and Illustration, which “offers images with simple shapes, clear lines, and colorblocking.” (A third Sketch style will appear in a future release, and you can use ChatGPT in Writing Tools to create images in many other styles.) You can also create images directly in Messages, Freeform, Keynote, and other apps.

Once you’ve entered a few words of description or selected a person, you can embellish the image by tapping the buttons for suggested themes, costumes, accessories, and places. Each addition causes Image Playground to generate a new image, and swiping left on that image pushes it to try again. Tap the ••• button to save or share an image you like. Saved images become available on all your devices.

Genmoji Spice Up Chats on the iPhone

Less ambitious but potentially more fun are Genmoji, which are custom emoji that you create with text descriptions. Want to emote about the cold to a fellow musician? Create an emoji featuring two cellos wearing scarves.

To do this, switch to the emoji keyboard, tap the Genmoji button to the right of the search field, and describe your desired emoji. As with Image Playground, you can keep swiping left on the generated image to create more variations. When you get what you like, tap it to insert it into your chat or document.

Remember that a single emoji sent by itself in Messages is quite large; two or three emoji are medium-sized, and inserting any more than that or adding text causes them to display at the smallest size.

Created Genmoji are added to your emoji collection on all your devices, but they’re actually stickers. You can remove them by tapping the ⊕ button in Messages, tapping Stickers, and using touch-and-hold on a Genmoji to access the Remove button. You can’t create Genmoji in macOS right now, but Apple has promised that feature for a future release.

Image Wand Cleans Up Apple Pencil Sketches

In iPadOS 18.2, the Notes app now offers an Apple Intelligence-powered Image Wand tool for those taking notes with an Apple Pencil. Make a rough sketch with your Apple Pencil, select Image Wand, draw a circle around your sketch, and Image Wand will turn it into a polished image. If your circle also contains text, Image Wand considers it when building the final image.

Visual Intelligence Explains What You See

When you upgrade to iOS 18.2 on an iPhone 16, the Camera Control button gains a new capability: Visual Intelligence. Press and hold it (whenever the Camera app isn’t already open, since that will trigger video recording), and Visual Intelligence presents Ask and Search buttons on either side of the shutter button. Tapping Ask causes ChatGPT to describe the image and lets you pose follow-up queries, and tapping Search performs a Google reverse image search; tap any of the results to load it. (If you can’t immediately tap Ask or Search, press the Camera Control button again or tap the shutter button to freeze the image temporarily.)

Siri Channels ChatGPT

Perhaps the most anticipated enhancement to Apple Intelligence is the integration of ChatGPT into Siri. Unfortunately, if your goal is to converse fluidly with ChatGPT, you may be better off using OpenAI’s ChatGPT app, perhaps triggered by the Action button or a widget. The problem is that unless you explicitly direct a Siri query by starting with “Ask ChatGPT,” Siri may try to answer with its own Web search or trigger a command, leading to inexplicable and unhelpful responses. Even when you get Siri to ask ChatGPT for a response, there’s no option to have it read back to you aloud, as with ChatGPT’s Advanced Voice Mode.

If you want to use ChatGPT through Siri, turn the feature on in Settings > Apple Intelligence & Siri > ChatGPT. While you’re there, you’ll probably want to turn off Confirm ChatGPT requests, which otherwise ask if you want to use ChatGPT every time it comes up. Although it may not be obvious, once you’re in a conversation with ChatGPT, you can keep talking as long as the Siri animation continues around the edge of the screen. Unfortunately, you cannot scroll back to any previous response while Siri is channeling ChatGPT; for full transcripts, you must revert to the ChatGPT app or website.

ChatGPT Enhances Writing Tools

The final place ChatGPT appears in Apple Intelligence is in Writing Tools, which may be more useful than its Siri integration. The new Compose option leverages ChatGPT to generate content wherever you’re writing, and you can also use it to create images using ChatGPT’s image-generation capabilities. Writing Tools also now allows users to request their own changes to selected text (including recasting it as a haiku, for example) instead of relying solely on the canned options to make the text friendlier, more professional, or more concise.

To do this, bring up Writing Tools in any app (by choosing Edit > Writing Tools > Show Writing Tools or Control-clicking selected text and choosing from the Writing Tools menu). Tap Compose and describe what you want ChatGPT to create. If it’s not quite what you want, which is likely, keep asking for refinements or go in a different direction.

What’s Next for Apple Intelligence?

Although this second wave of Apple Intelligence features largely fulfills Apple’s main promises, a few major additions remain for 2025. Most notable are significant changes to Siri that will enable it to take your personal context—your email, messages, and photos, for instance—into account. Siri will also gain onscreen awareness to include what you see in its responses. Finally, Apple is giving Siri access to hundreds of new actions in Apple and third-party apps, which should make it more capable of acting on your behalf. The other notable upcoming change is Priority Notifications, which will evaluate the notifications from all your apps and help you focus on the most important ones.

We also hope Apple will continue to refine and improve the existing Apple Intelligence features. While they’re well integrated into the overall Apple experience, they seldom measure up to ChatGPT, Claude, Gemini, and other leading AI systems.

(Featured image by Apple)

Apple slipped a significant new feature into Mail in iOS 18.2 that has nothing to do with Apple Intelligence: Categories. Like Gmail and other email apps, Mail can now automatically categorize messages into four buckets: Primary, Transactions, Updates, and Promotions. The idea is that categories make it easier to pay attention to important messages while collecting other messages for later processing. Tap the buttons at the top to switch between categories.

Oddly, Categories are currently available only on the iPhone. To maintain the same email experience across all Apple devices, you’ll have to wait for future versions of Mail on the iPad and the Mac.

Here are answers to questions we’ve heard about Mail Categories.

Can You Turn Mail Categories Off?

Apple turned Categories on by default in iOS 18.2, but not everyone appreciates the change. If you have your own organizational system, find the extra sections distracting, or just want to see all your email in one list, you can turn the feature off. Tap the ••• button at the top right of the Mail screen and select List View.

It’s also possible to keep Categories turned on but still see all your messages in a simple chronological list. Swipe left on the line of buttons to switch to an All Mail category that shows exactly what you’d see in List View.

What Appears in Each Category?

With Categories turned on, Mail automatically separates your mail into four categories:

• Primary: Personal messages, plus time-sensitive information from another category
• Transactions: Order confirmations, receipts, and shipping notices
• Updates: News, mailing lists, newsletters, and social media updates
• Promotions: Sale announcements, new products, coupons, and anything commercial

These categories are built-in, so you can’t select some but not others. Nor can you add your own.

Is There a Way to Recategorize Messages?

Unfortunately, Categories isn’t very good at categorizing messages at the moment. (Perhaps it should use Apple Intelligence!) In particular, we see newsletters and other items that should be in Updates incorrectly showing up in Promotions. Fortunately, you can easily recategorize messages from particular senders so Mail can correctly categorize similar messages in the future. How you recategorize messages depends on whether a message is in Primary or another category. For messages in Primary, tap the left-pointing blue arrow at the bottom of the screen and then tap Categorize Sender. For messages in other categories, tap the ••• at the top right of the screen and then tap Categorize Sender.

In either case, tap the desired category on the next screen and confirm your action.

The main problem with recategorizing is that messages from discussion-based mailing lists may be identified by their senders, not the list, so you may have to recategorize every sender from the list separately.

Why Are Messages from the Same Sender Grouped?

When you open a message in Transactions, Updates, and Promotions, you may be surprised to see a digest view that displays all the other messages from that sender. It’s often a helpful way to keep like messages together. Opening a message shows the most recent message, but you can scroll to see the rest. Whether you scroll up or down depends on whether Settings > Apps > Mail > Most Recent Message on Top is turned on. Additionally, how many lines appear in the message view depends on what you’ve selected in Settings > Apps > Mail > Preview.

Not a fan of the sender groups? You can turn the feature off for each of Transactions, Updates, and Promotions by tapping the ••• at the top right and deselecting Group by Sender.

What Are Priority Notifications?

If you’re using an iPhone 15 Pro model or any iPhone 16 with Apple Intelligence turned on, you may see priority notifications on the Primary screen. It’s designed to surface the most important messages, as determined by Apple Intelligence. If you don’t like it, tap ••• in the upper right and deselect Show Priority.

Overall, Mail Categories feels like Apple is playing catch-up with other email apps. If it works with your email stream and you find it useful, that’s great. But if not, don’t hesitate to turn it off and return to your familiar email workflow.

(Featured image by iStock.com/Giulio Fornasar)

An unheralded feature in iOS 18.2 and iPadOS 18.2 helps you manage the default apps on your iPhone and iPad. A default app is one that opens automatically for a particular function, like opening a Web link or inserting a saved password. Previously, the only way to change a default app was within the settings for that app, but now you can go to Settings > Apps > Default Apps to see and set all your options in one place. The Calling and Messaging options are new in 18.2, but Apple hasn’t yet given any third-party apps permission to appear in those lists. This new screen isn’t that big of a deal, but we wanted to use it as a reminder that alternatives to Mail and Safari might better fit your needs.

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

While we typically advise caution when considering upgrades to the latest major macOS release, we believe Apple has sufficiently refined macOS 15 Sequoia to warrant an upgrade for those interested. You don’t need to upgrade immediately, but there are no significant reasons for most people to delay further.

The big win in upgrading now is that Apple has released betas of most of its promised Apple Intelligence features for Macs with Apple silicon. In other posts, we’ve looked at the artificial intelligence-driven features that arrived in macOS 15.1 and macOS 15.2, including:

• Writing Tools for proofreading, rewriting, summarizing, and composing text
• Clean Up in Photos for removing background objects, plus natural language searches
• Audio recording in Notes, with transcription and summarization
• Summaries replacing snippets in Mail message lists, plus summarization of long messages or threads
• A Smart Reply feature in Mail and Messages for quick replies
• Notification summaries that reduce distractions from chatty apps
• Integration of ChatGPT with Siri
• Image Playground for generating custom images based on your descriptions

Sequoia has been quite stable, with two caveats. First, there have been some networking issues related to Apple’s built-in firewall and VPNs; we don’t yet know if macOS 15.2 resolves these. Second, macOS 15.2 introduced a new bug that causes problems for backup apps trying to make bootable backups on Apple silicon Macs. Although that’s annoying and will likely be fixed shortly, Apple has been deprecating bootable backups for years in the name of security. The modern approach is to install macOS from macOS Recovery, then use Migration Assistant to restore from Time Machine or a data-only backup.

Apple will continue to release macOS updates in 2025. If past performance is any indication, you can expect macOS 15.3 in January, 15.4 in March, and 15.5 in May with a few new features, plus a few security and bug fix updates in between.

That said, you can put off the Sequoia upgrade as long as you’re running macOS 13 Ventura or macOS 14 Sonoma and are staying current with Apple’s security updates. Earlier macOS versions no longer receive security fixes, rendering them more vulnerable to attack. Possible reasons to continue delaying include:

• You’re too busy. The upgrade process will take a few hours, plus some additional time to configure everything properly afterward. When you are ready to upgrade, aim for when a little downtime will be convenient.
• You rely on incompatible software. The jump from Ventura or Sonoma to Sequoia isn’t a big one, so most modern apps should have been updated by now. But if a necessary app is known to have issues, you’ll either need to wait for an update or switch to an alternative that works.

Sequoia may not transform your experience of using a Mac, but it has new features you might appreciate beyond Apple Intelligence. The most noticeable is probably iPhone mirroring, which lets you use your iPhone in a window on your Mac. Also potentially interesting are its new window tiling features that let you quickly arrange windows, the standalone Passwords app, Highlights and Distraction Control in Safari, and collapsible headers in Notes.

Before You Upgrade

Once you’ve decided to upgrade to Sequoia, 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 Sequoia-compatible versions.
  
• Clear space: Sequoia may need as much as 25 GB of free space to upgrade, and the Sequoia installer itself is nearly 15 GB, so we recommend making sure you have at least 50 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 in Sonoma or Ventura by choosing System Settings > General > Storage; in earlier versions of macOS, choose About This Mac from the Apple menu and click Storage. System Settings provides quick ways to free up space. Another easy option for iCloud Drive users is to Control-click large folders and choose Remove Download to “evict” the local versions of those files temporarily; Box, Dropbox, and Google Drive have similar features.
  
• Make a backup: Never, ever install an update to macOS without ensuring you have at least one current backup first. In an ideal world, you’d have an updated Time Machine backup, a data-only duplicate, and an Internet backup. That way, if something goes wrong, you can quickly revert.
  

Upgrading

After completing those tasks, ensure you won’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.

To initiate the upgrade, open System Settings > General > Software Update in Sonoma or Ventura (System Preferences > Software Update in previous versions of macOS), click the Upgrade Now button, and follow the instructions. If you’d like more guidance, check out Joe Kissell’s ebook Take Control of Sequoia.

After You Upgrade

Part of the reason to set aside plenty of time for your Sequoia 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 setup by asking for your Apple ID password, your Mac’s password, and, if you have another Mac, its password. Don’t worry that malware has compromised your Mac—these authentication prompts are fine.
• Some apps may have to ask for various permissions even though you previously granted them. Again, that’s fine.
• 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 (or Login Password on a non-Touch ID-enabled Mac). In older versions of macOS, 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 you to log in again. However, if you’re using a password manager like Apple’s Passwords or 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 Sequoia!

(Featured image by Apple)

We regularly warn Internet users about online scams and phishing attacks. Most of these are relatively easy to identify and avoid once you’re aware of telltale signs. Unfortunately, we’ve encountered a newer type of scam that’s more difficult to identify, partly because it plays on fears of legal action.

Website owners are the target of this scam email, which purports to come from a lawyer. The message states that an image on your site has been used without permission. Such a claim is all too believable for many, especially those who may not have been as careful about usage permissions in the distant past as they are today. The message includes a link to the image, a link to the purportedly infringing page, and a threat to initiate legal action if certain actions aren’t taken within five business days

Unusually, the email doesn’t ask you to take down the infringing image or pay a retroactive licensing fee. Instead, it says you must credit the image’s copyright holder and include a link. Such a simple request seems like a huge win—instead of paying a licensing fee or worrying about being sued, you can twiddle a little HTML and move on with your life.

Don’t do it! This is what’s called a “link insertion scam.” It exploits the search engine optimization principle that links on reputable sites provide legitimacy to linked sites, helping them move up in the search rankings. Unfortunately, the reverse is also true; linking to a scammer from your website will cause Google and other search engines to penalize your site in the search rankings.

Unfortunately, these copyright infringement scams look legitimate at first glance, as you can see in this example. The From and Subject lines don’t seem forged or malformed, and there are no obvious grammatical errors or indications that the writer doesn’t speak fluent English. And when you click the link in the signature, you end up at what appears to be the website of a real law firm. What should you do if you receive a message like this?

First, don’t panic. Just because the message looks legitimate doesn’t mean it comes from a real lawyer. Also, don’t call your lawyer unless they’re willing to work for free. You can save stress, time, and money by evaluating the message yourself.

A few details in the message suggest that it’s not real:

• The domain in the From line’s email address—elitejusticeadvisors.biz—sounds sketchy and doesn’t match the company name.
• The Subject line of “DMCA Copyright Infringement Notice” sounds official, but those familiar with the DMCA will know that it can be used only for a formal notice-and-takedown process, not to make demands for attribution or payment. But most people won’t know that.
• The message is addressed to the generic “Dear owner of,” whereas legitimate messages from a lawyer would be addressed to a specific entity.
• The required link URL points to a telecom news site in Sri Lanka, and it’s odd that an Arizona lawyer would be working for such a client.
• The example of the purportedly infringing image is hosted at Imgur, a consumer image-hosting site known for funny pet pictures and cringeworthy GIFs. Legal firms would always use some sort of case management site.

Those details may feel wrong, but they’re insufficient to prove it’s a scam. You’ll need to dig deeper. Here are some ways you can do that:

• Investigate the domain: Do a Web search on the domain in question: elitejusticeadvisors.biz. Because others have written about this scam, articles identifying it as a scam will appear on the first page of the results.
• Search for the lawyer and firm: The lawyer’s name is too generic to yield revealing results, but if you do a Web search on “Dean Parker Commonwealth Legal Services,” you’ll once again see that others have identified it as a scam.
• Check a state bar association directory: Most state bar associations or state courts have a searchable directory of licensed legal professionals. A quick search of the State Bar of Arizona’s member directory reveals that no “Dean Parker” is licensed in Arizona.
• See if the headshot matches a real person: If the website provides a headshot, you can copy the image (Control-click it and choose Copy Image) and paste it into the TinEye reverse image search engine. Since all the results say “generated.photos,” it’s a good bet that the image was AI-generated.
  
• Search for the company’s full name and address: As with the name of the lawyer, the generic-sounding name of the law firm will probably match other companies. However, if you search for the full name and address, you’ll likely turn up articles about it being fake.
• Visit the address virtually: With Apple Maps and Google Maps, you can verify that a business is present at a location (or not) and often view the offices using Google Street View. Both mapping tools show no law firm at the provided address. Additionally, the building does not have a fourth floor, as specified in the address.
  
• Ask ChatGPT: Now that ChatGPT has access to current Web information, it’s worth pasting the complete contents of the message into a ChatGPT conversation and asking it to tell you about the message. Start generally, but then ask if it thinks the message might be a scam, and if so, to suggest ways you could verify your suspicions.

Some of the above search suggestions identify the scam only because the scammer has reused the same company name, lawyer name, physical address, and website. If you were the first to be targeted by a new scam, the state bar association search and physical address check would be the most likely to expose it.

Let us leave you with an important caveat. You shouldn’t assume that all copyright infringement messages are scams. A legitimate DMCA takedown notice will ask you to remove the content, and a real copyright infringement message—probably from a company that specializes in such matters rather than a lawyer—will likely demand payment. In both cases, take down the offending image right away. If you really were using an image without permission, some payment may be required, and if the amount feels excessive, contact a lawyer specializing in copyright infringement cases. They may be able to negotiate a lower payment or point out issues that will make the claim go away.

(Featured image based on an original by iStock.com/Olivier Le Moal)

Alongside this year’s crop of operating systems comes Safari 18, the latest version of Apple’s Web browser. Most of what you do in Safari depends on the websites you use, of course, but Apple has added a handful of features aimed at improving your overall browsing experience, including Highlights, Distraction Control, a redesigned Reader, and Video Viewer.

We’ll focus on the Mac with macOS 15 Sequoia, but these features other than Video Viewer are also available on the iPhone and iPad with iOS 18 and iPadOS 18. Macs still running macOS 13 Ventura or macOS 14 Sonoma can get Safari 18 but miss out on the Highlights feature. Regardless of platform or macOS version, you access all these new features from the Page menu at the left of Safari’s address bar, which takes over from the previous Show Reader View button in Safari 17.

Highlights

Sometimes, when you visit a website, you just want a quick bit of information, like a restaurant’s address or a store’s hours. For those running Sequoia, once you turn on Safari 18’s Highlights feature, the Page menu icon in Safari’s address bar will show a purple sparkle if it detects information on the page that it can call out for you. Click it to learn more.

It can be hard to predict what Highlights will call out. It’s fairly reliable at showing location and business information extracted from Maps, and it may display biographical information about people on pages about them. For long articles, it may provide a quick summary you can use to see if it’s worth reading more. Apple says Highlights will also offer quick links to learn more about people, music, movies, and TV shows.

Distraction Control

Every website wants you to SUBSCRIBE TO A NEWSLETTER! and WATCH OUR VIDEO! and SHARE THIS ARTICLE! It’s exhausting. In Safari 18, Apple has added a feature that can help you turn down the volume on websites that constantly try to lure you into doing something other than what you intend. Distraction Control lets you remove annoying parts of a Web page. It works on nearly anything on the first use, but Apple warns that “hiding distracting items will not permanently remove ads and other content that updates frequently.” (That’s what most people want, of course, but such a capability would anger advertisers and publishers whose business models rely on ads.)

To clean up a Web page, click the Page menu and choose Hide Distracting Items. Then, move the pointer over areas of the screen you want to remove—if Safari can identify an item as a discrete object, it will gain a blue outline. Click it to make it disappear in a cloud of digital dust. Additional clicks will remove more items; Safari keeps count in the location bar. Click the Done button in the location bar to save your changes, or click Cancel if you were just testing. As you can see in the right-hand sidebar of the Yahoo page in the image below, the result is a cleaned-up view with much less distraction.

Redesigned Reader

Another way to eliminate distractions when reading on the Web is to use Safari’s Reader mode. When you click the Page menu and select Show Reader, Safari reformats the text and images in an article, removing extraneous ads and gewgaws. Once you’re in the redesigned Reader, click the Page menu icon again to access the customization options that let you choose from four color themes, nine different font faces, and various zoom levels

With Apple Intelligence on a Mac with Apple silicon, Reader also offers to summarize long articles. It may also provide a table of contents if the article contains appropriate headings, but it’s hard to predict when that will work.

Video Viewer

Finally, those who watch a lot of Web video will appreciate Safari 18’s new Video Viewer, available only on the Mac. Whenever you’re watching a video embedded in a Web page, clicking the Page menu reveals a new Video Viewer command. Choose that to expand the current video to fill the Safari window, overwriting whatever else might have been on the page so you can focus on the video.

Once you’re in the Video Viewer, switching to another tab in Safari or another app whose window obscures at least half the Video Viewer window causes Safari to switch to Picture in Picture, moving the video to a small window that floats above all other apps. You can resize that window and move it to any screen corner while it’s open, and it remembers its size and location for subsequent uses. Although multiple tabs and windows can use Video Viewer simultaneously, only one can be in Picture in Picture at a time.

Even if these changes aren’t world-changing for everyone, they make Safari an ever more capable Web browser, so it’s worth giving them a try to see if they’ll improve your Web experience.

(Featured image based on an original by iStock.com/Kanoke_46)

One of macOS 15 Sequoia’s most noticeable additions is a new form of window tiling. Drag a window to the menu bar to expand it to fill the screen, to the left or right edge to resize it to half the screen, or to a corner to resize it to that quarter of the screen. As you drag, a white outline shows what will happen when you drop the window. Unfortunately, accidentally invoking window tiling can be surprising and disruptive. The easiest way to ensure that dragging windows tiles them only when you want is to open System Settings > Desktop & Dock, scroll down to the Windows section, and turn off “Drag windows to screen edges to tile” and “Drag windows to menu bar to fill screen.” The important setting to leave turned on is “Hold Option key while dragging windows to tile” because from now on, your windows will tile only when you Option-drag them.

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

Employers and their employees part ways for all sorts of reasons. People may move on because of a contract’s completion, to take a new job, or because they’re retiring. Employees may also leave due to being laid off or fired. Whatever the reason, offboarding—the process of managing an employee’s departure from an organization—is essential.

Without a systematic offboarding protocol, organizations face significant risks related to data security, device mismanagement, operational disruptions, and compliance violations. In a particularly troubling example, a fired employee allegedly hacked Disney World’s menu creation system, changing prices, adding profanity, and—most problematically—adjusting allergen information in ways that could have caused someone allergic to peanuts to order food that contained them.

Obviously, offboarding has various administrative aspects. We’ll focus on those associated with technical infrastructure, but it’s also important to consider how you’ll communicate internally about the departure and any human resources and legal matters.

Our overarching advice regarding offboarding is to establish a formal protocol so everyone knows what’s involved. That’s particularly important for departures that happen with little notice. When building your offboarding plan, consider these three parts of the process: revoking access, retrieving devices, and preserving the organization’s data.

Revoke Digital Access

When offboarding an employee, the most important thing to consider is how you’ll revoke their digital access to organizational resources such as email, a shared password manager, and core service accounts. For those who are retiring or staying to train their replacement, access revocation can proceed gradually on a schedule. This approach provides sufficient time to transition ongoing projects and communications.

However, in most cases, it’s safest to revoke access immediately, especially when an employee has been terminated involuntarily due to layoffs, performance problems, or misconduct, or when dealing with employees in high-security roles, such as IT administrators, members of the legal team, or high-ranking executives. Even if their departure isn’t contentious, the risk of data leakage is too high.

Revoking access is significantly easier if you’re using Apple Business Manager and an MDM platform. Because Apple Business Manager lets you use federated Apple Accounts, it’s simple to revoke access to iCloud and other Apple services. Plus, because Apple Business Manager makes it possible to separate personal Apple Accounts and their associated data, employees can move their personal data off an organization’s device more easily.

MDM—mobile device management—is even more important because it enables administrators to revoke access to organization-managed email accounts, VPNs, Wi-Fi networks, and cloud services. If a device isn’t returned, an MDM platform can remotely lock, wipe, or reset it. For BYOD scenarios (Bring Your Own Device, where employees use their own devices rather than organization-owned ones), a properly configured MDM allows the removal of organizational data and profiles without affecting personal data.

Using an identity provider like Google Workspace, Microsoft Entra ID, or Okta with a single sign-on system makes revoking access even more straightforward. These services tie access to an organization’s apps, resources, and devices to a single login, so deactivating a departing employee’s account in the identity provider instantly cuts off access to all connected systems. Otherwise, you’ll find yourself doing the dance of deactivating Google, then Adobe, then Slack, and so on. It’s tedious and potentially error-prone.

Finally, the combination of an MDM system with single sign-on can also help monitor employee behavior during the offboarding period for unusual activities. You’ll want to know if a terminated employee logs in to a confidential database that they have no reason to access immediately after receiving notice.

Retrieve Organization Devices

Another key aspect of your offboarding plan should revolve around retrieving organization-owned devices. Even if you can use MDM to revoke access, you need to get your devices back so they can be given to other employees or held in reserve as backups. Apple Business Manager helps here, too, since it tracks all registered devices owned by the organization and can reassign devices to new users.

The real win of Apple Business Manager in this regard is that it lets you turn off Activation Lock on all supervised devices, whether it was turned on using a federated Apple or personal Apple Account. Without Apple Business Manager, you may have to work with the employee to regain access to the device. If that’s not possible, Apple support may be able to help unlock the device if you can provide proof of purchase and ownership.

To ensure you don’t end up in such an awkward situation, follow these best practices when using Apple Business Manager:

• Make sure to purchase Apple devices through Apple Business Manager-compatible channels.
• Use Automated Device Enrollment to ensure that devices are supervised and managed by MDM out of the box.
• Rely on federated Apple IDs to ensure the organization retains control over organizational content within Managed Apple Accounts.

Preserve Organization Data and Communications

Finally, think about what the departing employee was doing. You’ll want to transfer or archive everything they worked on, including their organizational email account. In most cases, someone else will have to take over their responsibilities and may need access to emails, files, contacts, and more.

An identity provider can help by transferring ownership of cloud-based files and other data stored in Google Workspace or Microsoft 365. Without one, you’ll have to review all their online files and reassign ownership manually.

Email requires additional thought. You’ll probably want to forward the departing employee’s email to whoever is taking over. If that’s not feasible, set up an auto-reply explaining that the employee is no longer available and providing alternative contacts. In that case, it’s also worth scanning the incoming email periodically to ensure essential communications aren’t being missed.

Next Steps

If you don’t have a formal offboarding policy, we recommend developing one soon to ensure that you aren’t at risk for data security, device mismanagement, or operational disruptions. It’s one of those tasks that are easy to put off until it’s too late, at which point you have to scramble. You can find offboarding policy templates and other resources online, and we’re happy to discuss the tech-specific aspects when you’re ready.

Of course, if you’re not already using Apple Business Manager and an MDM solution, getting started with them is even more important to implement right away. Contact us to discuss what’s involved.

(Featured image by iStock.com/yacobchuk)

In macOS 15 Sequoia, Apple made it more difficult to bypass Gatekeeper to run apps that aren’t notarized. (Notarization is one of the ways Apple ensures that apps distributed outside the Mac App Store are unmodified and free from malware.) Cybercriminals have responded to this increase in security with a new social engineering attack. They provide the victim with a disk image, ostensibly to install some desired piece of software, instructing the user to drag a text file into Terminal. Doing so executes a malicious script that installs an “infostealer” designed to exfiltrate a wide variety of data from your Mac. The simple advice here is to treat any guidance to drop a file into Terminal with extreme suspicion—no legitimate software or developer will ever ask you to do that.

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

Finder icons sometimes hint at their file’s contents, but if you find yourself opening file after file to look at the contents quickly, the Mac has a little-known feature just for you: Quick Look. To give it a spin, select a file in the Finder and press the Space bar or Command-Y. If Quick Look supports that type of file, it instantly displays a standalone window showing the contents of the file without opening it in its native app. Press the Space bar again to close the window.

If the document you’re previewing has multiple pages, you’ll see thumbnails along the right side that you can scroll through using your mouse or trackpad, or by pressing the Page Up/Page Down keys. But you aren’t limited to just viewing a file: click the Open With button to open the file in its default app, or click the Share button in the upper right to send it to someone else via email, Messages, or another sharing service. PDFs and images will also show the Markup button that lets you annotate the file directly, and images have a Rotate button.

If you need to scan through a set of files in a folder, you can press the arrow keys while the Quick Look window remains open—how you move among the files depends on the Finder window’s view. In List view, for instance, using the Up and Down arrow keys can be a great way to browse through a collection of pictures. You can even interact with the Finder while using Quick Look, which means you can delete an unwanted photo by pressing Command-Delete while previewing it.

Quick Look works well for evaluating or comparing multiple files. Select a bunch of files and press the Space bar to open them all in Quick Look. The Left and Right arrow keys let you cycle through your selection; there are also Back and Forward arrow buttons at the top left of the Quick Look window. To the right, you’ll see a Thumbnail button that displays the selected files in a grid—click any thumbnail to focus on just that item.

To remove the distraction of your desktop, click the Zoom button in a Quick Look window. If you have multiple files selected, you can even start a simple slideshow from the zoomed Quick Look window—it’s a quick way to show off a folder of images. Another way to get to a zoomed Quick Look window is to select the files in the Finder and press Option-Space.

What file types does Quick Look work with? Not everything, but out of the box, Quick Look supports text files, RTF files, HTML files, images, audio, video, PDFs, iWork documents (Keynote, Numbers, and Pages), Microsoft Office files, fonts, and more. Third-party apps can extend Quick Look to support proprietary formats, and developers have released independent Quick Look extensions. Many people appreciate these three extensions:

• Folder Preview (free) displays the contents of folders in Quick Look.
• BetterZip (free for viewing) lets you look inside Zip archives and other compressed files.
• Peek ($7.99) not only supports 530 file types but also lets you copy, search, navigate, and more directly within the Quick Look window.

Although it’s best known in the Finder, Quick Look is available elsewhere on the Mac, including the examples below, so it’s always worth selecting what you want to preview and pressing the Space bar to see if it works.

• Spotlight: Preview search results to see if they’re what you want
• Open dialogs: Preview files before you open them
• Time Machine: Preview versions of files before restoring them
• File transfer apps: Preview files on remote servers before downloading
• Messages: Preview files added to conversations before opening them
• Mail: Preview attachments to email messages

To manage your Quick Look extensions, open System Settings > General > Login Items & Extensions, scroll to the bottom, and click the ⓘ button next to Quick Look.

Finally, note that if your Mac has a trackpad, you can invoke Quick Look by force-touching a Finder icon (press deeply until you feel a click) instead of pressing the Space bar.

Quick Look takes just moments to learn, but it can save you hours of time poring through files on your Mac!

(Featured image by iStock.com/megaflopp)