Using the Jamf Pro API to retrieve FileVault personal recovery keys

As part of Jamf Pro 10.43’s release, Jamf has added the ability to access and retrieve FileVault personal recovery keys via the Jamf Pro API:

• Return FileVault information for a specific computer: https://developer.jamf.com/jamf-pro/reference/get_v1-computers-inventory-id-filevault
• Return paginated FileVault information for all computers: https://developer.jamf.com/jamf-pro/reference/get_v1-computers-inventory-filevault

For those who want to use this new capability, I’ve written a script which uses the Jamf Pro Classic API and Jamf Pro API to take a list of Jamf Pro computer IDs from a plaintext file, retrieve the associated Macs’ FileVault personal recovery keys and generate a report in .tsv format.

For more details, please see below the jump.

Use of FileVault Institutional Recovery Keys no longer recommended by Apple

When legacy FileVault was first introduced as part of Mac OS X 10.3 Panther in 2005, it supported a recovery key method which used a special keychain named FileVaultMaster.keychain which by default had a private key and public key inside. This recovery key was used to provide certificate-based authentication to unlock the encrypted disk images which were used by legacy FileVault.

When FileVault 2 was announced as part of Mac OS X Lion in 2011, Apple announced that there would be two kinds of recovery keys available:

1. Personal recovery keys (PRK) – These are recovery keys that are automatically generated at the time of encryption. These keys are generated as an alphanumeric string and are unique to the machine being encrypted. In the event that an encrypted Mac is decrypted and then re-encrypted, the existing personal recovery key would be invalidated and a new personal recovery key would be created as part of the encryption process.
2. Institutional recovery keys (IRK) – These are pre-made recovery keys that can be installed on a system prior to encryption and most often used by a company, school or institution to have one common recovery key that can unlock their managed encrypted systems.

IRKs were the sole part of Apple’s FileVault 1 (also known as legacy FileVault) that was carried over into FileVault 2. IRKs were legacy FileVault’s recovery keys and they were used in almost exactly the same way. The main difference was that they were now used to unlock an encrypted disk as opposed to legacy FileVault’s disk images.

In FileVault 1 deployments, you were asked to set a Master Password when turning on FileVault 1’s encryption. When you set the Master Password, the FileVault 1 encryption process set the password that was entered as the password on the /Library/Keychains/FileVaultMaster.keychain file. In turn, the FileVaultMaster.keychain file contained two keys used for PKI certificate-based authentication (one public key and one private key). When the public and private keys are both stored in one keychain, the keychain can be used to unlock your FileVault 1-encrypted home folder in the event that the password to open it was lost or forgotten. The Master Password only unlocked the keychain and allowed the system to access those two PKI keys. This is the reason why you needed to set the Master Password before encrypting and why it was also important to use the same FileVaultMaster.keychain file across the machines where you wanted to make sure that the same recovery key was being used.

If you were deploying the same recovery key for your FileVault-encrypted Macs, Apple consistently recommended that you go into the FileVaultMaster.keychain file, remove the PKI private key, put the private key somewhere secure and deploy the FileVaultMaster.keychain file with only the public key inside. The reason was that, in the event that the password to the FileVaultMaster.keychain file was compromised, all the compromiser got was one half of the keypair (the public key half.) The private key would not be on the machine and thus not available to compromise the FileVault 1-encrypted homes on the machine. However, FileVault 1 would work with both the public and private keys stored in /Library/Keychains/FileVaultMaster.keychain.

In FileVault 2, Apple changed removing the private key from being a suggested best practice to being a technical requirement. If you want to use an institutional recovery key, your FileVaultMaster.keychain file needs to have just the public key in it. If both public and private keys are stored in the /Library/Keychains/FileVaultMaster.keychain file on a Mac, FileVault 2 will ignore the keychain and not use it as an institutional recovery key. In this case, enabling FileVault 2 encryption will automatically generate a personal recovery key.

That was then, this is now

Over the years, the PRK gained functionality while the IRK largely did not. With the advent of PRK escrow systems (found in most present-day MDM solutions), the IRK’s main advantage of being a recovery key which could be mass-deployed came to seen instead as a weakness. After all, better to have recovery keys where each encrypted drive has its own unique key in place of the danger of a compromised recovery key being able to unlock all the machines in your Mac environment.

You can also only use an IRK to unlock or decrypt if you were booted to macOS Recovery. Recovery’s limited functionality meant that users of an IRK would have to do some preparation work, including making sure that the IRK’s keychain file was available somewhere which could be reached from Recovery.

Meanwhile, Apple has made changes to the environments where you could use an IRK. Beginning with macOS Catalina, macOS Recovery now prompted you to log in with either a password associated with an admin user or with a PRK.

You could not use an IRK at this login screen. So now Mac admins found themselves in the situation where they had an IRK, but couldn’t use it to authenticate in Recovery and get to the point where they could use the IRK.

With the introduction of Apple Silicon Macs, Apple has also discontinued Target Disk Mode functionality. This also affected the use of IRKs because it removes the ability to unlock using an IRK while the locked drive is connected to another Mac via Target Disk Mode.

The combination of all of these factors has led to Apple making a written recommendation to not use IRKs for institutional deployments of FileVault on Macs.

It’s been a long run for IRKs and they still do work as recovery keys (for now), but in my opinion it’s time to follow Apple’s stated recommendation and stop the deployment and use of IRKs as FileVault recovery keys.

FileVault login screen differences between Intel and Apple Silicon Macs

As new Apple Silicon Macs (ASM) have begun making their way to organizations which use FileVault encryption to secure their fleets, a difference between Intel Macs and ASMs has become apparent.

Intel Macs:

• Supports account icons and password blanks at the FileVault login screen
• Unable to support username blanks at the FileVault login screen
• Unable to support smart cards for login at the FileVault login screen

ASMs:

• Supports account icons and password blanks at the FileVault login screen
• Supports username and password blanks at the FileVault login screen
• Supports smart cards for login at the FileVault login screen

Why the differences between platforms? For more details, please see below the jump.

Erasing a FileVault-encrypted T2-equipped Mac

Normally, reinstalling macOS on a Mac is a straightforward process:

1. Boot to macOS Recovery
2. Select Reinstall macOS from macOS Utilities.

3. Follow the onscreen instructions.

However, if you have a Mac equipped with a T2 chip where FileVault is turned on, there’s an extra step involved. When you boot to macOS Recovery on a T2 Mac with FileVault on, you will be prompted for the password of an account on the Mac which has admin privileges.

If you don’t have the password to any of the accounts which appear, you can select the Forget all passwords? option.

This will bring up a new screen where you can enter a FileVault Personal Recovery Key.

If you can provide either the account password or the personal recovery key, the next thing you should see is the macOS Utilities screen.

 

What if you don’t have either a password or a personal recovery key? Is your Mac now a paperweight? For more details, please see below the jump.

Managing macOS Catalina’s FileVault 2 with fdesetup

Since its initial release in OS X Mountain Lion 10.8.x, Apple’s main tool for managing FileVault 2 encryption has been fdesetup. With the transition from managing Core Storage-based encryption on HFS+ to managing the native encryption built into Apple File System completed, this well-developed toolset continues to be Apple’s go-to tool for enabling, configuring and managing FileVault 2 on macOS Catalina.

With its various functions, fdesetup gives Mac administrators the following options for managing FileVault:

• Enable or disable FileVault 2 encryption on a particular Mac
• Use a personal recovery key, an institutional recovery key, or both kinds of recovery key.
• Enable one or multiple user accounts at the time of encryption
• Get a list of FileVault 2-enabled users on a particular machine
• Add additional users after FileVault has been enabled
• Remove users from the list of FileVault enabled accounts
• Add, change or remove individual and institutional recovery keys
• Report which recovery keys are in use
• Perform a one-time reboot that bypasses the FileVault pre-boot login
• Report on the status of FileVault 2 encryption or decryption

For more details, please see below the jump.

Managing macOS Mojave’s FileVault 2 with fdesetup

Since its initial release in OS X Mountain Lion 10.8.x, Apple’s main tool for managing FileVault 2 encryption has been fdesetup. With the transition from managing Core Storage-based encryption on HFS+ to managing the native encryption built into Apple File System completed, this well-developed toolset continues to be Apple’s go-to tool for enabling, configuring and managing FileVault 2 on macOS Mojave.

With its various functions, fdesetup gives Mac administrators the following options for managing FileVault:

• Enable or disable FileVault 2 encryption on a particular Mac
• Use a personal recovery key, an institutional recovery key, or both kinds of recovery key.
• Enable one or multiple user accounts at the time of encryption
• Get a list of FileVault 2-enabled users on a particular machine
• Add additional users after FileVault has been enabled
• Remove users from the list of FileVault enabled accounts
• Add, change or remove individual and institutional recovery keys
• Report which recovery keys are in use
• Perform a one-time reboot that bypasses the FileVault pre-boot login
• Report on the status of FileVault 2 encryption or decryption

For more details, please see below the jump.

Mouse doesn’t move at FileVault login screen in VMware Fusion macOS Mojave VMs

As part of working with FileVault on macOS Mojave, I’ve been using VMs running in VMware Fusion 11.x for testing. As part of that, I’ve seen a problem where the mouse doesn’t move when the VM has booted to the FileVault login screen. The keyboard responds and arrow keys can be used to select users, but the mouse itself is immovable and does not respond.

After some research, I ran across someone who had the same issue and found a workaround. For more details, please see below the jump.

Re-syncing local account passwords and Secure Token on FileVault-encrypted Macs running macOS Mojave

As part of FileVault on Apple File System, Apple introduced a new account attribute called Secure Token. As mentioned in a previous post, Secure Token can present some interesting problems for Mac admins who work with FileVault-encrypted laptops. Among the potential complications are these scenarios:

• “I changed the password for my local account, but only the old password is being taken at the FileVault login screen.”
• “We’ve lost the password to the only local user account with a Secure Token, so now we can’t enable any other accounts on this Mac for FileVault.”

Usually, this happens because the local account password in question was changed outside of the Users & Groups preference pane in System Preferences and now Secure Token and the account password are out of sync with each other.

Up until the past few days, the only fix I knew of for that situation was to back up the data and wipe the drive. However, it looks like there is a workaround for encrypted Macs which fixes the password problem and sorts out Secure Token in these scenarios. In both cases, a personal recovery key will be needed as the way to authorize the needed changes. For more details, please see below the jump.

Unable to enable FileVault on macOS Mojave

As part of FileVault on Apple File System, Apple introduced a new account attribute called Secure Token. Secure Token can present some interesting complications for Mac admins and among them is this scenario:

“The laptop is decrypted, but we can’t re-enable FileVault now.”

Usually, this happens because the account password was changed outside of the Users & Groups preference pane in System Preferences and now Secure Token and the account password are out of sync with each other.

Up until today, the only fix I knew of for that situation was to back up the data and wipe the drive. However, it looks like there is a workaround that fixes the password problem and sorts out the Secure Token attribute for the account on a decrypted laptop. For more details, please see below the jump.

Unlock your FileVault-encrypted boot drive using Disk Utility on macOS Mojave

In the event that you need to unlock an unbootable FileVault-encrypted boot drive on macOS Mojave, it’s possible to do so using Disk Utility and the password to a FileVault-enabled account on the drive.

For more details, see below the jump.