Apple’s iPhone User Guide for iOS 27 explains how to export your passwords for websites and accounts to a CSV file, which you can then import into another password manager. The option sits in the Settings app under Apps, then Safari, and Apple warns that the exported file is not encrypted. That makes the export […]

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Way back in January I noted that one of the features that had kept me from using Passwords as my only password management app was its inability to manage SSH keys, a feature offered by competitor 1Password. What I liked about 1Password’s approach was that it abstracted this feature, letting me authenticate my keys using macOS’s built-in authorization system. So instead of typing in a passphrase for that key, I could just use Touch ID or type my 1Password password. This still seems to me like the kind of thing that Passwords should offer, and I still hope that it might in the future.¹

In the meantime, I’ve recently turned to Secretive, an open-source tool by Max Goedjen and others that allows you to store your SSH keys inside your Mac’s Secure Enclave. Doing so means that your keys can’t be exported and are protected by the same level of security as your system’s most sensitive data. In addition to ECDSA-256 keys, running Secretive on macOS Tahoe and later lets you create post-quantum keys using the MLDSA-65 and MLDSA-87 algorithms. If you don’t know what any of that means, don’t worry about it—you’re fine.

Using Secretive still requires some technical know-how. You’re going to have to edit some configuration files and, if you’re using the keys to log in to remote servers, install them yourself. There are instructions for much of this both in the app and online. Other apps can work with Secretive too, assuming the developers have built in support: right now, it’s mainly targeted at developer tools like git and GitHub, as well as secure file transfer clients like Transmit and Cyberduck.

The one major downside of this system is that since the private keys are stored in the Secure Enclave, they cannot be backed up or transferred elsewhere. That’s more secure, but it’s more inconvenient as well; if your Mac gets hosed, or you migrate to a new device, you’ll have to recreate your keys all over again. It also means that if you maintain SSH keys on multiple Macs, you have to set up Secretive on all of them. That’s another reason that I’d like to see Apple find a way to abstract this process further via the Passwords app, if it can figure out a safe and secure way to do so—not to mention, potentially making it available on iOS as well. Like passkeys, ssh keys offer more security and less reliance on passwords.

Secretive’s not for everybody, but there are certainly a subset of users who will be very interested in the security it offers. But until such a time as Apple makes this process part and parcel of its operating system, I’ll be relying on Secretive to help me manage it.

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.]

I remain unhappy with Apple’s passkey backup story. There’s little documentation about this, but from what I can tell:

• There are no automatic versioned backups. (Syncing is not backup because it doesn’t protect you against human error, bugs, or attacks.)

• Even if you have a Time Machine backup, it’s not possible to restore it to the same Mac without logging into iCloud. This could be a problem if your account is locked or compromised.

• Restoring it to a different Mac is impossible because the decryption key is stored in the other Mac’s Secure Enclave. Apple is protecting you from accessing your own backup, even though the keychain is already an encrypted file, protected by the password that you set. (And the Time Machine or clone drive that it’s stored on is probably encrypted, too.)

• The Passwords app can now export passkeys, but you cannot create an export file that you can import back into Passwords on another Mac. You can only export to a third-party password manager that’s installed on the same Mac (which may require a working Apple account). Even then, this does not include passkeys for Apple services; they don’t show up in the Passwords app. There are also some other restrictions around shared items and Sign In with Apple.

The above is last year’s news, but I don’t think I had written it all in one place before. The new bad news is that, as of macOS 26.4, these problems now affect regular passwords, not just passkeys. (You do have more flexibility to export passwords, though.)

Rich Trouton (Hacker News):

Historically, you could copy the login keychain file from one Mac to another and be able to open it on the destination Mac by providing the password to that keychain. As of macOS Tahoe, this does not appear to work for Macs which use Secure Enclave.

[…]

From that, it appears that unlocking the login keychain requires more than the password because the keys it unlocks are tied to the Secure Enclave of the Mac where the keychain was created. With the decryption keys stored in the source Mac’s Secure Enclave, manually copying the keychain to another Mac and then unlocking it won’t work. The password you have for the keychain may be correct, but the actual keys needed to decrypt its contents won’t be available on the destination Mac.

Jeff Johnson:

According to Apple, all Apple silicon Macs, as well as some Intel Mac models, have the secure enclave processor, so the issue affects millions of Mac users.

[…]

If anything happens to your Mac, if it’s stolen or becomes inoperable, your login keychain is also lost, unrecoverable, even if you have a copy of the login keychain file! This is a stunning development that has left me bewildered and irate. WTF was Apple thinking? To my knowledge, Apple did not even publicize the change in Tahoe.

[…]

How does Migration Assistant handle the situation on Tahoe? I don’t know. I would guess that since Migration Assistant still has access to the old Mac, it simply decrypts the old login keychain and copies the login keychain entries to the new login keychain on the new Mac, rather than transferring the keychain files directly.

[…]

I recommend that you open your login keychain with the Keychain Access app (now located in /System/Library/CoreServices/Applications) and check what’s in there, the data that you’re in danger of losing. Whether you realize or it not, many apps use the login keychain. For example, Google Chrome and other Chromium browsers store passwords in the login keychain. MailMate stores email account passwords in the login keychain. The open source RSS reader Vienna stores website passwords in the login keychain. The Zoom app also uses the login keychain. My Developer ID code signing certificate is stored in the login keychain; if I’m not mistaken, I believe that Apple’s own Xcode put it there. And of course, any items that you’ve manually added to the login keychain would be lost if the keychain file could not be unlocked.

Howard Oakley:

I have confirmed that a login.keychain-db copied from my Mac mini M4 Pro to a virtual machine (VM) running macOS Tahoe 26.6.2 cannot reveal any of its secrets to the Keychain Access app on the VM, as it refuses to accept the valid password. Not only that, but Keychain Access running in a VM cannot access the login.keychain-db keychain copied from another Tahoe VM, although neither has been anywhere near a Secure Enclave.

If you intend migrating manually between Macs, don’t waste time trying to copy across the login keychain, as it’s not likely to work, and its secrets will remain.

[…]

I performed test migrations between VMs, and demonstrated that Migration Assistant does copy the contents of the login keychain successfully to the destination Mac.

I think this only happens if you migrate over a network, with the old Mac acting as a server. I prefer to connect the old Mac using Target Disk Mode, but in that case Migration Assistant wouldn’t be running on the old Mac so the special sauce wouldn’t work. Likewise if I were trying to do the migration using a third-party cloning app.

Howard Oakley:

• Loss of physical access to a Mac running 26.4 or later prevents access to any items stored in its login keychain.
• Hardware failure requiring logic board replacement may have the same effect on restoring the contents of its login keychain (assuming that migration from a backup doesn’t work).
• Restoring an Apple silicon Mac in DFU mode may be similar in effect.

What I don’t know yet is whether you can unlock and access any login keychain written by macOS 26.4 or later and migrated from a backup accessed directly from a different Mac. This would occur in one-Mac migration, when Migration Assistant uses a backup of a Mac not acting as a Migration server. This would only be possible if the backup also stored the additional secret required to access the login keychain, which seems unlikely.

[…]

Apple’s documentation for macOS Tahoe and the copying of keychains makes no mention of this change, in spite of its serious consequences and the change being made almost six months ago.

It there states “If you didn’t use Setup Assistant, the best way to copy your keychains to a new computer is to export and then import them using Keychain Access”. However, Keychain Access can only export some keychain items including certificates and keys, but not passwords. And to do that, the Mac must be able to unlock and access those items in the source keychain. Thus, Apple’s recommendations are out of date and will now fail.

rsUSA0 (via Jeff Johnson):

When upgrading to macos 27 Golden Gate, I erased my system through recovery to do a clean install. I planned to manually migrate data back to the computer from an external drive clone of Macintosh HD and a Time Machine backup. This has worked well in the past and eliminated system bloat.

When I manually migrated my login keychain, it opened, showed entries, but it wouldn’t accept my password to reveal any actual passwords. The window shakes like I’m using the wrong password. I’m 100% sure I’m using the correct password. I also tried every password I’ve ever used and I’m certain it’s not a password issue.

Perhaps even restoring to the same Mac failed because the clean install wiped the key stored in the Secure Enclave. [Update (2026-10-01): See update below.]

Jeff Johnson:

Some people who read my previous blog post misunderstood the issue, because they didn’t know that the macOS login keychain is distinct from iCloud Keychain.

[…]

In the Keychain Access app, you can see two separate default keychains, one of which is the login keychain. The other default keychain is named “iCloud” if you’ve enabled iCloud Keychain, “Local Items” if not. There’s actually a longstanding issue with this keychain analogous to the newer issue with the login keychain.

[…]

Mac users like myself who forsake iCloud Keychain face the prospect of no disaster recovery for the Local Items keychain. My habit is to manually create a new password item in the login keychain and only then supply the credentials to an app, for example, Safari AutoFill. Ironically, the login keychain change brought by macOS 26.4 sabotages my password backup procedure[…]

jen1x:

Today, I got my new Mac mini M6. When I started setting up the new machine, it asked me to update to macOS 27, so I followed the instructions.

[…]

After signing in to iCloud, it asked me to enter the passcode of one of my Apple devices. I entered the correct passcode and even tried the passcodes for all of my devices, but I keep getting the same message:

Verification Failed
There was an error verifying the passcode of your iPhone

I don’t like having to rely on iCloud.

Previously:

• SuperDuper’s “Follow-Up”
• macOS 26.4
• 2025 Six Colors Apple Report Card
• Locked Out of Apple Account Due to Gift Card
• Downloading Xcode With a Passkey
• iOS and iCloud Keychain Are Hostile to Backups
• Passkeys Credential Exchange
• Passkeys: A Loss of User Control?
• Fixing iCloud Keychains, and Backing Them Up

Update (2026-10-01): TN3137 has been updated for macOS 26.4:

Historically each file-based keychain was a standalone file. You could, for example, copy a keychain file from one Mac to another and still use it, as long as you knew the keychain password.

In macOS 26.4 and later that’s no longer the case. A keychain file might reference a protected entropy file. To unlock such a keychain you need both the keychain password and the protected entropy file.

[…]

These protected entropy files are stored in /var/db/SystemKeys. If you’re creating a backup product, make sure to back up that directory. Without it, the keychain files that you back up might be useless.

[…]

The /var/db/SystemKeys directory is not directly accessible, even when running as root, so you can’t copy a protected entropy file in the normal way. To access it, disable System Integrity Protection (SIP).

First things first: I don’t think turning off SIP every time you make a backup is a real solution. And I don’t understand what problem Apple is really trying to solve with protecting the entropy file; it seems like they don’t trust their own encryption. Lastly, it’s not explicitly stated, but I don’t think copying the entropy file helps with backing up passkeys.

That aside, I find the details both illuminating and confusing. This probably explains the rsUSA0 case above, where restoring to the same Mac didn’t work. The key wasn’t stored in the Secure Enclave but rather in the entropy file on the SSD, which had been wiped. This also suggests a simpler way for Migration Assistant to work; it could have special access to copy the entropy file without having to actually open the keychain.

It also seems to be saying that, if you turn off SIP and copy the entropy file, you can then access your keychain backup from another Mac. But I’m not sure how to square that with Apple’s keychain documentation:

Keychain items are encrypted using two different AES-256-GCM keys: a table key (metadata) and a per-row key (secret key). Keychain metadata (all attributes other than kSecValue) is encrypted with the metadata key to speed searches, and the secret value (kSecValueData) is encrypted with the secret key. The metadata key is protected by the Secure Enclave but is cached in the Application Processor to allow fast queries of the keychain. The secret key always requires a round trip through the Secure Enclave.

How can copying the entropy file work if the Secure Enclave is required? My guess is that the entropy file itself is encrypted (NSFileProtection) using the Secure Enclave. So accessing it on the original Mac does require going through the Secure Enclave. But when you make a backup, the entropy file gets decrypted. Maybe accessing the keychain on the second Mac causes file protection to be re-applied to the contents of /var/db/SystemKeys, so then it becomes protected by that Mac’s Secure Enclave.

Previously:

• Accessing the Keychain Without the Password

Update (2026-10-02): Dave Nanian (Mastodon):

This is obviously not a good user solution, because no one is going to boot to Recovery, turn off SIP, back up, boot back to Recovery, and turn SIP back on. Thinking they would do so is kind of crazy.

[…]

SuperDuper handles this situation. When you make a bootable copy, the required keys are copied without requiring any special steps.

SuperDuper itself can’t read the entropy file, but it uses Apple’s asr tool to make bootable backups, and that has special access. (Unfortunately, it can’t update the entropy file without making a fresh bootable backup, but in practice I don’t expect it to need updating.) I had not been bothering to make most of my backups bootable, since in most cases I just want to restore to an internal SSD, not actually boot from the backup. But I now think it makes sense to choose bootable backups as the default.

Howard Oakley (Rich Trouton):

I won’t expand on my feelings any further than by saying that in my 37 years as an Apple developer, I have never come across anything so shameful.

Unfortunately, it seems like the keychain stuff was just the warm-up act.

Update (2026-10-05): Howard Oakley:

[macOS 26.4] Added the protected directory at /var/db/SystemKeys to backups of Data volumes, and protects them in backups.

So Time Machine does back up the entropy file. I missed this because I didn’t see /var/db in my backups, but it turns out that they do have /private/var/db/SystemKeys and are just missing the /var symlink.

Update (2026-10-07): Jeff Johnson:

The -s option to the security show-keychain-info is not yet documented in man security, not even on the latest version of macOS Golden Gate. Moreover, the -s option does not work on macOS Sequoia and earlier. In general, the security show-keychain-info command reveals no information unless the specified keychain is unlocked, which makes it impossible to discover the salt of a keychain file that you can’t currently unlock. However, as long as you already have the entire contents of the /var/db/SystemKeys directory from the macOS volume on which a keychain file was created, the inability to determine the keychain file’s salt beforehand shouldn’t be much of a problem, because in practice there are typically only a few salt files, so you can simply copy them all to another macOS volume.

[…]

You don’t actually have to disable SIP to add files to the /var/db/SystemKeys directory, because you can do so from another boot volume. You have to boot into recovery anyway in order to disable SIP, so you could simply edit /var/db/SystemKeys from recovery rather than disabling SIP on the non-recovery volume.

The security unlock-keychain command lacks an option to specify the location of an entropy file or to provide the file data directly, so unfortunately a login keychain can’t be unlocked from the recovery volume, only from a volume where you can add files to the /var/db/SystemKeys directory.