One of the most bizarre and sometimes useful features added in macOS 27 Golden Gate is contextual naming in the Finder, as well as other places where a name for a file is useful, using Apple Intelligence.¹ I say bizarre because it’s easy to be surprised by what’s filled in—or that anything but Untitled Document or Untitled Folder appears.

Meanwhile, if you want to rename a big batch of files, you can opt for a little-known feature built right into the Finder, or dramatically increase your power with a third-party utility.

Apple Intelligence has some suggestions

There’s not much to using Golden Gate’s automatic file naming, which is the delight of a feature that’s discoverable, self-explanatory, and useful:

1. Select a file name or folder name in the Finder, wait a moment, and single-click it, so that the name becomes highlighted.
2. Wait a moment. Because Apple Intelligence is involved, some behind-the-scenes analysis of the item’s contents takes place.
3. A drop-down list of suggestions appears, which may or may not match what you want. If one does, click it. This replaces the file or folder name.

You will also see suggestions appear in Apple’s apps when you save a currently untitled document, as well as when you transfer files via AirDrop or text an image to a person or group. I’ve noticed when I text a screenshot on my iPhone, the name “Screen Image” appears in the message text without any detail.

As you can imagine, results vary. However, I’ve found in my testing that Apple Intelligence does a reasonably good job. This includes looking at what a photo or image file represents and suggesting a name derived from that—a kind of hidden Visual Intelligence.

If you don’t like this feature, go to Finder: Settings: General and uncheck “Suggest file names.”

It has a number of limitations:

• Names aren’t always suggested. This may be because Apple Intelligence has evaluated that the current name is better than one it could offer, or because the query times out or is determined to take too much computational time.
• There’s no feedback when it fails—no message appears that says “no suggestions available,” or the like.
• It doesn’t always use the current name as a context clue or, seemingly, pull from our private information to which Apple Intelligence has access. For instance, I clicked a file called “glenn as a freshman,” a photo taken long ago and far away, and the Finder suggestions were: “Person with Hand on Head” and “Person in Thought Pose.” Not inaccurate, but not specific. However, a folder I clicked offered suggestions derived from the folder name.
• Images with controversial elements may not receive suggestions. A picture of my older child from 15 years ago, dressed in a lobster costume that many people thought was a devil costume, gets no suggestions, while other photos of the same type, size, and time period do.
• You can’t get suggestions for a batch of files or folders, only one at a time.

Batch rename your files and folders

Apple introduced a built-in automatic renaming feature in Finder with OS X 10.10 Yosemite. It’s limited, but functional, and if you only need some basic replacing, prefixing, or suffixing of names of a group of files, it will do the trick for free.

Long before Apple built basic renaming into Finder, I began to rely on A Better Finder Rename ($30 for all current version updates) by Frank Reiff.² It lets you apply rules to rename files or folders you select, which can include extracting information from metadata in each file to apply unique information from it.³

Each renaming pattern is created in the Actions list. So if you want to renumber files and apply EXIF metadata, you can do that as two separate Actions, as shown in the screenshot.

There are many Actions categories, each of which has context-specific choices for renaming. I’ve used A Better Finder Rename in the past to fix a folder with hundreds of images that were named arbitrarily to extract the capture date, allowing for better sorting. I’ve also used it for picayune tasks, like making sure all the screenshots for an article for Six Colors had the same prefix, to make them easier to find after uploading.

What’s in a name?

In an era in which Spotlight works as advertised, coupled with the new capabilities in Siri AI, do we even need well-named files? Oh, yes, indeed. I would argue that the more sensibly named your files are, the less time you waste trying to find what you need. Visually scanning names organized at least lightly into some kind of folder hierarchy will always provide better results than searching, even today.

This battle has raged since the introduction of the Mac—nay, since the introduction of file names! Good names save time, no matter how well-indexed the contents.

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

Apple stuffs a lot of different kinds of tasks into Messages. It’s a junk drawer for communications with other people. Send photos? Sure. Set up a safety partner for when you are going somewhere? Why not. Pay somebody? Of course! And, yeah, let’s stick in a poll!

But I think the best use beyond text and media of Messages is sharing your location. It’s a convenient way to share your whereabouts with someone else or a group, either indefinitely or for a fixed time period. Starting in the version 27 operating systems, you don’t have to use Apple’s preset periods, either: you can set a custom duration, which can be up to 30 days.

Sharing your location in Messages is an extension of Apple’s Find My service and native apps. You can also share your location within a native Find My app—that’s on an iPhone, iPad, Mac, or Apple Watch, not iCloud.com’s Find My, which only works with devices.

Like everything with Find My, your current location is locked down except to share with those you explicitly permit, and only for the period you choose, or indefinitely.

Methods of sharing location

Messages offers two different ways to share your location:

• As continuous access: With iMessage, you can let someone see where you are as you move about for one hour, one day, or a custom period (in version 27 releases), or you can add them indefinitely to the list of people who can see your whereabouts in Find My.

• As a pinned location: You can share your current location as a pin on a map, sent as an image preview with a link to Apple Maps. You can send this snapshot using SMS/MMS, RCS, or iMessage.

Starting in the version 27 operating systems, you can also hide your location via Messages (in the Info pane, tap or click Hide My Location) or the Find My app without the other person being notified. They’re also not told when you resume sharing.

Share your location via iMessage

Apple still hasn’t unified how location is shared in Messages across its four platforms, so I have to explain two divergent paths to the same result. (This is a bit overdue for Messages non-text/media features in general!)

Here’s how to share your location on an iPhone, iPad, or Apple Watch in Messages:

1. Select or start a conversation.
2. Tap the plus (+) button and choose Location.
3. A Location view appears at the bottom of the conversation showing a preview of your current location. Tap Share and then tap For One Hour, For Today, Always, or Custom. (These names appear slightly differently in releases before the version 27 operating systems.)
4. If you picked Custom, choose your duration, anywhere from 15 minutes to 30 days, and tap Start Sharing. On an Apple Watch, that starts location sharing; on an iPhone or iPad, proceed to the next step.
5. Tap the Send (up arrow) button to start sharing your location.

A Request button appears if the other person isn’t sharing their location with you. Tap it to request their location.

If you’re already sharing your location with someone, there’s no duration prompt, and the Share button is labeled Send instead. You’re essentially just sending them a reminder with a link they can tap to open Find My.

On a Mac, follow these steps to share your location:

1. Open Messages.
2. Click the profile or profiles at the top of the conversation thread to reveal the Info pane.
3. Click Share My Location.

Where are you?

Apple determines your location from an iPhone, Apple Watch, or iPad, and shows you which device in the Find My app’s Me view under My Location. If you use Messages to offer your location to someone from another device, you’re alerted “Another Device Used for Your Location” and given an option to Cancel or Continue. With iPhone Handoff, which lets two iPhones share one number, your location follows the currently active phone.

After you send your location, the other person or people have access to it. They see a Location card in the conversation that continuously updates to show where you are.

They can tap Open Find My to see you within the Find My app or, if they’re not already sharing their location with you, tap Share My Location to reciprocate.

Likewise, when someone shares their location with you, it appears in the Info pane of any conversation they’re part of. If their current location is known, this tile adds more details; if it can’t be determined, a message says their current location is unknown.

Inset into the location section, you see their current city or landmark, a label showing how recently their location was updated, and a button. The time label appears as minutes or hours, Now (within the last minute or so), or Live (real time). The button shows the walking or driving time; tap or click it to open Maps with directions. Their location updates in real time as they move, which helps if you’re trying to meet up.

You can’t undo sending your current location, but in the Info pane in Messages, in any version of iOS, iPadOS, or macOS, you can tap or click Stop Sharing My Location to cut off the flow of location data.

Apple’s addition of Hide My Location in the version 27 releases lets you silently stop sending your location without alerting the person you’re sharing with. You can also resume from the same spot in the Info pane (or in Find My). The other person only sees your location is unavailable if they check. The reason to add this feature is both to allow privacy or safety, depending on with whom your location is shared. (Abusive partners or controlling family members often force people to enable location sharing.)

Share a pinned location via SMS/MMS or RCS

SMS/MMS and RCS can’t be used to share ongoing location information, but you can send and receive a pinned location with them via Messages, though only on an iPhone, iPad, or Apple Watch:

1. Select or start a conversation.
2. Tap the plus (+) button and choose Location.
3. A Location view appears at the bottom of the conversation showing a preview of your current location. Tap Send Pin.
4. A Location link for Apple Maps appears, labeled Dropped Pin, with your current address below it.
5. Tap the green Send (up arrow) button to send your location.

For further reading

For much more about Find My tracking, location privacy, deflecting stalkers, and AirTags and the Find My network, see my book Take Control of Find My and AirTags. It’s been fully updated for the version 27 releases.

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

Apple introduced iMessage within Messages in 2011 as its house-brand, end-to-end encrypted messaging product. The promise of iMessage is that posts are always encrypted, using servers and technology developed by Apple and controlled by it. The encryption keys reside on your device, stored so Apple can’t access them, and no third party should ever have the leverage to retrieve them. (There’s a big proviso there, which I’ll explain at the end of this article.)

Despite exploits uncovered over the many years since iMessage first appeared, the core protocol has never been breached, only device exploits or iCloud-backup extractions that allowed access to stored messages. That’s a strong track record. Apple has continued to tinker with improving iMessage encryption, while also adding an optional method of ensuring conversation integrity, Contact Key Verification.¹

But in researching the update for Take Control of FaceTime and Messages, a lengthy ebook that covers those two apps plus the Phone app ², I discovered you could be lulled into a false sense of security based on what you assumed iMessage was and was not.

The odds of this change in standards causing a security breach and your messages being exposed seem unlikely, at least right now. But after scrolling through conversations and seeing what’s going on, I feel Apple has omitted important signals for users when iMessage suddenly stops being used during a conversation.

When is an iMessage not an iMessage?

Messages supports four kinds of communications, each with its own encryption standards and limitations, except for iMessage:

• iMessage: iMessage is always encrypted, but you may not always be using iMessage in an iMessage conversation, which is a confusing thing to say—bear with me.
• RCS: The Android-standard RCS is encrypted only if every non-Apple device in the conversation has a recent-enough version of RCS that supports encryption and its carrier also allows it.³
• SMS/MMS: SMS and MMS are never encrypted. (SMS allows text only; MMS supports rich media and group messaging. RCS is intended as the ultimate replacement for MMS.)

Apple sensibly organizes messages into conversations: a series of messages with another person or in the same group of people. However, that presentation method intentionally hides most of the details about how different communications protocols may be used within a single conversation. Apple likes to keep things simple.

As you start a conversation, Messages offers all sorts of visual signals that let you know when you’re using iMessage, as reassurance and branding:

• The person’s email address or phone number appears in blue.
• At the very start of the conversation, iMessage appears on a line by itself and a lock icon plus Encrypted appears on the next line. (You can always scroll way back to the start of a conversation and find this.)
• In the conversation, your messages are shown in blue.
• Click or tap the conversation profile image or images, and in the Info pane, at the very bottom, a message in gray in small type notes “All iMessage conversations are securely encrypted end-to-end, so they can’t be read while they’re sent between devices.”

That feels like a lot of reinforcement of the point! And, when you’re using iMessage, you probably expect you’re always using it throughout a conversation. But within an iMessage conversation, things can go wrong, and the system downgrades to the next commonly available option.

The hierarchy of Messages standards ranks, from most to least desirable:

• iMessage
• RCS with encryption
• RCS
• MMS
• SMS

The impact of that hit me while revising my book: when iMessage isn’t available, Apple tells you only inline. Despite all the information Messages displays about iMessage being encrypted, the inverse state is faint. This kind of negative knowledge, or information about something not happening, can often be as important as something that does happen. A warning about a fuel tank approaching empty is the kind of information every driver (or pilot) needs, for instance. If you think end-to-end encryption—or Apple-based encryption—is critical for you, then a pop-up message or other warning is what you would expect.

Look through the images in this story to see real-world examples I encountered this summer. In one, my wife and I are texting in a conversation that goes back almost two decades. For unknown reasons, Messages couldn’t perform a secure interchange—no security warning appeared, but something prevented iMessage from doing its usual handshake dance. So it defaulted without an alert to RCS, and noted that inline (see the figure’s top).

Because Messages supports RCS encryption, it can use it with other iCloud users, too, allowing encryption to continue even though it’s not iMessage encryption. Then, equally oddly, it went right back to iMessage (see near bottom).

If a conversation switches to an unencrypted communications method, there’s no warning; only, as you can see in another example, the gray inline message in a group chat of iMessage users (encrypted) shifted to unencrypted RCS when I added someone whose device didn’t support iMessage or encrypted RCS.

So how can you be sure what’s in use without scrolling around for sure? At any given time, the Info pane always shows the current state of encryption. This figure below shows two RCS conversations: on the left, an unencrypted one; on the right, an end-to-end encrypted session.

Because it’s RCS, Apple won’t vouch for the integrity of the session on the right! The Messages label reads “Apple can’t verify the software used on receiving devices,” and provides a link with more technical information and disclaimers. This is fair: Apple is relying on an infrastructure it doesn’t control.

With the above scenarios, I don’t believe Apple is putting us in jeopardy, nor do I think you should be particularly worried about it, unless you’re someone already in a high-risk category, like a political figure, human-rights advocate, or journalist. However, I keep thinking about how what we don’t know can still hurt us.

If you’d like to prevent Messages from downgrading security, you have options, although they may not be fully desirable. All of these are managed on an iPhone at Settings: Apps: Messages. You can’t control these message settings from an iPad or Mac.

• Disable downgrading to SMS: Turn off Retry as Text Message. This may mean some messages you send won’t get through. Also, this doesn’t prevent other people in an iMessage (or encrypted RCS conversation) from sending you SMS or MMS messages if they can’t transmit via iMessage.
• Disable RCS Messaging: In RCS Messaging, disable RCS Messaging. You can’t disable only non-encrypted RCS, which is a shame, as that would be my suggestion as the next best thing. Instead, you have to disable it entirely to prevent iMessage from downgrading to either unencrypted or encrypted RCS.
• Disable MMS Messaging: Messages may try to send MMS even when it doesn’t try to use SMS, so disabling MMS Messaging will prevent that as well.

This set of options and Messages’ presentation of encryption feels overdue for an overhaul.

Protecting Messages in iCloud

I mentioned at the outset there was a proviso about accessing stored messages. The one exception to the end-to-end encryption rule is if you have iCloud for Messages enabled. In certain configurations, someone who manages to gain access to your Apple Account could retrieve an iPhone or iPad backup, retrieve that backup, and use an encryption key stored in it to decrypt messages and extract your data. That someone could be a law-enforcement agency, not just a hacker.

Because the Messages in iCloud encryption key is stored in the clear in the backup, this is the one scenario in which Apple can be compelled to provide information under the right legal framework that would allow a government-connected agent to examine your iCloud-synced messages. This is also an exploit that a criminal or other party could take advantage of.

You can avoid this end-to-end encryption loophole in one of two ways:

• Enable Advanced Data Protection for iCloud. This option adds end-to-end encryption on top of nearly all your data (excluding email, calendar entries, and contacts) stored in iCloud. This is a good move generally, though there are drawbacks: you may lose full data recovery if all your devices are stolen, lost, or destroyed. See the complete list. (ADP is not available in the United Kingdom.)
• Disable iCloud Backups. Without backups, the Messages data isn’t archived via a restorable backup to iCloud, and thus the Messages in iCloud encryption key isn’t uploaded into that backup. Backing up to your Mac (or a Windows machine) requires more effort, though most of what you want to retain is likely synced via iCloud! Read this support document for the difference between iCloud Backup and backing up to a computer.

I suggest picking one. While, again, it’s unlikely your privacy would be breached, most of modern life feels like it’s about finding out how your privacy was, in fact, breached. Why not take action before that happens, however much we trust Apple’s infrastructure and integrity?

After my massive article on migrating your passwords, passkeys, and other secrets from third-party password managers to Apple’s Passwords, Wallet, Safari, and general ecosystem—potentially with help from another app—reader Scott asked whether I was directing people into weaker security. He wrote:

If someone manages to steal my device and its passcode, they have access to the contents of my phone, including all of the information stored in Apple Passwords. This is not the case if I use a third-party password manager and have set a separate password for access, as the thief will not have access to my other passwords…I’m surprised this liability is not discussed and considered more frequently.

This is a great follow-up question, and one that I didn’t address within the scope of the migration article, which was already long. Let me pick apart how to answer that by looking at risks and mitigations.

The risks of cracking our eggs at once

I understand the fear of losing everything, whether it is a set of material objects or digital secrets. One of the most heartrending stories I ever heard was from a photographer who lost all his work in an apartment fire shortly after moving to New York City to start his career. He rebuilt. That’s harder to do digitally, where if our privacy is “burned,” we might see bank accounts drained and potentially have to get our Social Security number or other identity number replaced.

But we should consider alongside that how likely it is for the scenario Scott describes: “…someone manages to steal my device and its passcode, they have access to the contents of my phone…” A sequence of actions has to take place for that to be true:

• Someone has to steal your device.
• Someone has to have obtained your passcode or have forced you to reveal it when or after they steal the device.
• That person has to then have the time to put the stolen booty to use, like performing money transfers or cryptocurrency actions, before you erase your device remotely.

It’s most likely an iPhone would be the thing stolen, because we have those with us all the time, and thieves have been known to shoulder surf or record video from a distance to capture you entering your passcode. iPads and Macs can, of course, be taken from us as well, but it’s just much less likely when we’re out and about. A stolen Mac has additional protections if it’s powered down, and we often set longer passwords for a Mac, where an iPhone or iPad might still have a four-digit code.

If you are a privacy advocate, protester, journalist, opposition politician, or promoter of freedom and peace, you are at greater risk, and thus using Passwords as an in-band solution—one in which compromising a device unlock pathway could compromise our secrets—already makes no sense. (I’ve seen some people recommend Bitwarden, not because of a necessarily superior security model, but because it’s open-source and has an expansive free personal tier that includes end-to-end encryption for synchronization among your devices.)

So this worry for the rest of us is a kind of prospective and speculative anxiety: that, in the wrong circumstances, all our passwords and other secrets would be exposed. While this happens regularly, the number of instances in which a passcode is obtained and malice occurs before we can stop it is fairly low. Most iPhones are stolen to wipe them for resale, which Apple has rendered difficult with the long-ago introduction of Activation Lock. Rather than knowing your passcode, criminals are more likely to try to threaten you or use phishing to obtain the passcode after they have the device.

Fortunately, Apple came up with a solution after the Wall Street Journal in 2023 exposed how a dangerous sequence of events, which could start with drugging or violence, would allow thieves to reset an Apple Account and take over someone’s digital accounts and life.

We don’t yet have face-stealing technology

Apple’s Stolen Device Protection is a feature that may be one that has irritated you enough that you haven’t cared to understand how it may also keep your secrets safe. Go to Settings: Privacy & Security: Stolen Device Protection, and it’s likely enabled. Based on reports, I believe Apple enabled this by default in iOS 26.4. It’s available only for iPhones.

When enabled, it restricts a number of activities and requires Touch ID or Face ID for many authentication steps—passwords can’t be used instead. For the purposes of protecting your secrets, Stolen Device Protection has two key attributes:

• It locks many actions for an hour, such as changing your Apple Account password. Even then, you have to use biometrics to start the countdown and before taking the action. Knowledge of a passcode isn’t helpful. If you have Away from Familiar Locations selected, this occurs only when the device isn’t in a place you routinely spend a lot of time, typically home and work.¹

• You cannot view passwords or fill them into form fields from Apple’s Passwords system without using Touch ID or Face ID with Always enabled, so a thief having your passcode is out of luck. (If you have Away from Familiar Locations selected, a ne’er-do-well would have to be in one of those locations to use a passcode.)

This leaves one rotten scenario, in which you are kept under duress for at least an hour and are forced to use biometrics, then perform other actions. But how likely is that for most people? I don’t want to dismiss the distress of those who have been through that, but the likelihood of most people experiencing it is vanishingly small.

Leaving Stolen Device Protection enabled does mean that you may have to wait an hour in some scenarios to manage aspects of your Apple Account, make changes to Face ID or Touch ID, change your device passcode, and a few other actions. But this minor inconvenience might assuage the kinds of concerns that Scott wrote in about, and make you more comfortable that your big basket of secret eggs won’t scramble.

For further reading

I just updated my book Take Control of Securing Your Apple Devices to incorporate changes Apple has made in the last year, including in iOS 27, iPadOS 27, and macOS 27. In the book, I dig into risks and likelihoods further. The book takes the tack that Apple, having secured a lot of our data, now has implemented many protections against physical access to our hardware, including theft, and explains how to enable, configure, and manage a wide set of features.

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

You ever have one of those moments when you start to copy a large file in the Finder and groan when the Progress Window tells you it’s going to take forever? I used to have them all the time, and it didn’t make sense until I figured out that macOS was gaslighting me about my network connection.

The other day, Friend of the site Todd Vaziri wrote on Mastodon:

Two M4 Mac minis, both running Tahoe on the same local network, gigabit ethernet, using standard File Sharing. I can’t reliably play a Blu-ray rip from one computer to another without it stuttering… a measly 2.82 Mbit/sec file. What am I doing wrong here?

I replied, as did many other people, to tell Todd that he could probably solve his problem by disconnecting both Macs from his in-house Wi-Fi network. He tried that, and all of a sudden, his file transfers were running at fast Ethernet speeds.

You’d think that your Mac would detect the fastest network connection available and prioritize that, but it doesn’t. There is, however, a very helpful setting you can use to prioritize your settings. You can find it in the Settings app, under Network. Scroll to the very bottom of that pane and click on the inscrutable downward-facing caret next to the inscrutable ellipsis symbol (yep, System Settings is still terrible four years later), and choose Set Service Order.

In the resultant window, you can drag all of your Mac’s possible network connections up and down to create a priority list. Items at the top are your Mac’s preferred network connections; ones at the bottom will only be used if there are no other active connections. If you put Wi-Fi at the very bottom, your Mac should only use it when no other active connections are available.

Except: It doesn’t work reliably, and hasn’t for years. Because I’ve been exactly where my friend Todd was the other day, baffled as to why my two Macs on fast Ethernet connections were chugging through an impossibly slow file transfer. The answer was solved the moment I manually disconnected from my Wi-Fi router.

So what is a Mac user to do? The obvious answer would seem to be to turn off your Wi-Fi, but that’s not advisable: Macs use Wi-Fi for all sorts of features beyond getting on the Internet. If you turn off Wi-Fi, you’ll lose access to Continuity features, including the ability to AirDrop.

Instead, the right way to approach this is to leave your Wi-Fi on, but not connected to any routers. As a convenience, any Wi-Fi network you connect to is set to “auto-join,” so when you see it again later, your Mac will reconnect. That’s great, but if you’re being bitten by this issue, that convenience becomes a frustration. Instead, open Settings, choose Wi-Fi, and click the ellipsis button at the far right side of your Known Networks list. You’ll be given a small menu of options, including the (presumably checked) Auto-Join. Uncheck this setting by choosing it, and now your Mac won’t automatically glom onto your local Wi-Fi network. Do this for any networks that your Mac might connect to when you’re trying to be on your at-home or in-office Ethernet.

There is a downside to this approach. When I unplug my laptop from its docking station and open it up somewhere in my house, I have to manually connect to my Wi-Fi network. And when I’m back at my desk, I need to manually disconnect. (These can both be handled by clicking on the Wi-Fi symbol next to the network’s name, right from the Wi-Fi menu in Control Center.) Gray means it’s not connected, white with an accent color means it’s connected.

Yes, it’s a little bit of a hassle. So you need to ask yourself: How much am I affected by my Mac inadvertently using my Wi-Fi connection when it’s also connected to a wired network? The answer may be “not at all,” in which case you should probably keep using Wi-Fi using the Auto-Join regimen that Apple uses as its default.

But if you’re like me, and have seen slow file transfers and unstable videoconference connections resolved by dropping off of Wi-Fi and back to Ethernet, you may find that manually connecting and disconnecting from Wi-Fi is a small price to pay for networking stability.

[Apple folks take note: I have re-filed this bug, “Network traffic often sent to wrong interface based on network priority,” as FB24893093 after originally filing it as FB16275329, which was closed in 2025 because it was theoretically fixed in a late Sequoia build. Either it’s back, or it never left.]