Archive for the ‘FileVault 2’ Category

Slides from the “FileVault 2 Decrypted” Session at MacAD UK Conference 2016

February 10, 2016 Leave a comment

For those who wanted a copy of my FileVault 2 talk at MacAD UK 2016, here are links to the slides in PDF and Keynote format.


Keynote –

FIPS 140-2 validation and FileVault 2

January 10, 2016 2 comments

One question I’ve seen which has caused confusion for folks who deal with security regulations is this: Is FileVault 2 FIPS 140-2 validated?

The answer is: Yes, depending on the version of OS X

The cryptography used by FileVault 2 on the following versions of OS X has gone through the FIPS certification process and has been validated as being as being FIPS 140-2 Compliant:

OS X 10.11 is currently in the process of becoming FIPS 140-2 validated. The reason El Capitan is not automatically FIPS 140-2 validated has to do with OS X’s CoreCrypto cryptography foundation and how the FIPS 140-2 certification process works.

FIPS certification

The FIPS certification process tests a specific cryptographic module used inside a system to protect information. It also applies only to a cryptographic module used in a shipping product; the cryptographic module in question can’t be a prototype or in beta. 

Another important thing to know is that the testing is very specific and applies only to the cryptographic module submitted for review. If the vendor changes anything in the cryptographic module, it loses its FIPS certification and has to be resubmitted for laboratory testing and government review.

There are three major phases in the process:

Phase 1: Design and Documentation

In order to prepare for the FIPS validation process, the cryptographic module in question has to be designed to pass the various tests involved and also be properly documented. This is the part of the process which the vendor has the most control over.

Phase 2: Laboratory Testing

Once the cryptographic module has been designed, documented and shipped, it is submitted to a third-party accredited Cryptographic and Security Testing (CST) laboratory to test the module(s) in question against FIPS 140-2’s qualitative levels of security. This testing can take an indeterminate amount of time, depending on how well the cryptographic module is designed and documented.

Best case: A cryptographic module that properly meets the requirements and with all required documentation written correctly can complete its laboratory testing in two to three months.

Phase 3: Government Review

After the lab has tested the cryptographic module, a report on the testing is submitted to the Cryptographic Module Validation Program (CMVP) for review. CMVP is a joint US-Canadian program that reviews all the test reports, with the CMVP Validation Authorities being the National Institute of Standards and Technology (NIST) for the US Government and the Communications Security Establishment (CSE) for the Government of Canada. This review can also take an indeterminate amount of time, depending on how many test reports need review, and can range from two months to eight months.

Apple and CoreCrypto

Apple’s CoreCrypto library is used by various components in OS X to provide low level cryptographic primitive support. This is the cryptographic library which is submitted by Apple to the FIPS 140-2 certification process.

With every version of iOS and OS X, Apple has made changes to CoreCrypto. As part of making those changes, Apple has had to resubmit CoreCrypto to laboratory testing and government review as part of the FIPS 140-2 certification process.

Apple’s stated intention is to continue FIPS 140-2 validation for OS X’s CoreCrypto cryptography foundation, which would also cover FileVault 2 on future versions of OS X, but the certification process itself can only be begun once that future OS has been released. Meanwhile, as noted above, the testing and governmental review process will take months to complete.

The good news is that it’s possible to at least see where Apple is in the process. NIST has a website where the current list of modules in the process can be viewed via a PDF which is updated weekly. To check for Apple’s progress, search the PDF for entries where Apple, Inc. is listed as the vendor.

Apple’s existing FIPS certifications are also available for reference via the link below:

Managing El Capitan’s FileVault 2 with fdesetup

December 20, 2015 2 comments

For the first time since fdesetup‘s initial release in OS X Mountain Lion 10.8.x, Apple has not added new features to fdesetup as part of a new OS release. Instead, fdesetup maintains the same set of features in OS X El Capitan 10.11.x as it had in OS X Yosemite 10.10.x.

This decision may mean that fdesetup, an essential command-line tool for enabling, administering and disabling Apple’s FileVault 2 encryption, is now considered by Apple to be a fully-developed toolset for managing FileVault 2.

fdesetup gives Mac administrators the following command-line abilities:

  • 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

I’ll be taking you through all of the capabilities mentioned above, with a focus on showing exactly how they work. See below the jump for details.

Read more…

FileVault 2 on Yosemite is now FIPS 140-2 Compliant

August 11, 2015 Leave a comment

Apple announced on Saturday, August 8th that the FIPS 140-2 validations for the cryptographic modules used by iOS 8 and OS X 10.10.x have now been completed. This is significant news for folks who want to use FileVault 2 in government and regulated industries (such as financial and health-care institutions.)

For folks who haven’t heard of it before, FIPS 140-2 is an information technology security accreditation program run jointly by the US and Canadian governments. This program is used by private sector vendors to have their cryptographic modules certified for use in US and Canadian government departments and private industries with regulatory requirements for security.

As part of the announcement, Apple has released KBase articles and guidance for security offices who deal with encryption:

OS X Yosemite: Apple FIPS Cryptographic Modules v5.0

Crypto Officer Role Guide for FIPS 140-2 Compliance OS X Yosemite v10.10

According to Apple, the OS X Yosemite Cryptographic Modules, Apple OS X CoreCrypto Module v5.0 and Apple OS X CoreCrypto Kernel Module v5.0, require no setup or configuration to be in “FIPS Mode” for FIPS 140-2 compliance on devices running OS X Yosemite v10.10.

FileVault 2 is listed as being FIPS 140-2 Compliant as part of the Crypto Officer Role Guide for FIPS 140-2 Compliance OS X Yosemite v10.10 documentation, in the Compliant Applications and Services section.

Screen Shot 2015 08 11 at 11 13 21 AM

For more information about the validation certification, please see below the jump.

Read more…

Yosemite’s paused encryption problem fixed in 10.10.3

June 10, 2015 4 comments

When Yosemite was released in October 2014, one of the changes it introduced was including a new FileVault 2 enablement option in Apple’s Setup Assistant. This option encouraged new users of Yosemite to enable FileVault 2 encryption and had the choice to enable FileVault 2 selected by default.

When the encryption process began, a significant issue then appeared for a number of users where the Mac would report Encryption paused during the encryption process, then never resume the encryption process.

Filevault stuck encryption paused


This produced a situation where the Mac could not complete encryption, but would not decrypt either because the encryption process had not completed. The only fix appeared to be deleting the existing CoreStorage volume, which addressed the issue at the cost of deleting everything stored on the boot drive.

Fortunately, OS X 10.10.3 includes a fix that should stop this issue from occurring on OS X 10.10.3 and later. There is also now a procedure that should fix Macs still affected by this problem. For more details, see below the jump.

Read more…

Stopping your Mac from booting to the FileVault 2 Reset Password wizard

May 27, 2015 7 comments

When a FileVault 2-encrypted Mac sits for more than a minute with an account selected at the FileVault 2 pre-boot login screen, a message like the one below should appear:

If you’re having a problem entering your password, press and hold the power button on your Mac to shut it down. Then press it again to start it up in the Recovery OS.

Screen shot 2015 01 15 at 1 40 50 pm

If the instructions are followed, the Mac will boot from the Mac’s recovery partition on the next startup and go into a FileVault 2 Reset Password wizard.

Screen Shot 2015 05 27 at 7 58 05 AM

In the Reset Password wizard, there are currently three options available.

  1. I forgot my password
  2. My password doesn’t work when logging in
  3. My keyboard isn’t working when typing my password to login

However, if you don’t want or need to use the Reset Password wizard, there’s not an obvious way to get back to the FileVault 2 pre-boot login screen. There’s no visible way to quit, and rebooting the Mac using the power button will return you to the Reset Password wizard.

Thanks to research by the folks in the ##osx-server IRC room, it looks like there’s a relatively straightforward way to reset the boot process:

  1. While booted to the initial Reset Password wizard screen, press and hold the power button on your Mac to shut it down
  2. Reset NVRAM
  3. Once the NVRAM reset procedure has been completed, let the Mac boot.

At that point, you should be taken to the FileVault 2 pre-boot login screen instead of the Reset Password wizard.

Screen Shot 2015 05 27 at 8 05 49 AM

Credit to arrose in the ##osx-server IRC room for figuring this out.

Update 5-28-2015: As elvisizer mentioned in the comments, there is also the option of revealing the hidden menu at the top of the screen and using the Startup Disk preferences to select your hard drive and reboot back to FileVault 2 pre-boot login screen. Since this is easier to show rather than explain, I’ve made a short video of the process.

Note: The password used to unlock the drive in the Startup Disk preferences can be the password of any account that appears on the Mac’s FileVault 2 pre-boot login screen. If you can log in at the pre-boot login screen, you should be able to enter your password to unlock.

Accessing the FileVault 2 Reset Password wizard via Yosemite’s Recovery HD

May 10, 2015 2 comments

I’d previously written a post about Yosemite’s FileVault 2 pre-boot recovery options and how they can be accessed via the FileVault 2 pre-boot login screen. This process uses a Reset Password wizard to help users recover from login problems at the FileVault 2 pre-boot login screen.

I recently learned that the FileVault 2 Reset Password wizard can also be manually launched while booted from the Recovery partition. For more details, see below the jump.

Read more…


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