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YubiKey macOS Setup

You bought a YubiKey - now what?

The goal is to outline the steps to configure your YubiKey in a sane method and to use it to maximize your security.

This guide is for users who are comfortable with the command line and various technical jargon.

This is highly opinionated on how you should and should not use your YubiKey but is organized well enough that you should be able to modify if you have a need.

The instructions have been tested on macOS 10.12 (Sierra) with a YubiKey 4 and YubiKey Neo. While there are sections that are OS independent, most of the tricky bits are macOS specific.

To perform these instructions, the YubiKey should be plugged into your computer's USB port.

Install some software

# For OSX
> brew install python3 swig ykpers libu2f-host libusb
> pip install yubikey-manager

Turn off OTP - AKA the random letters when you accidentally touch it

This will turn off One-Time-Password. Most users will not find OTP useful and will be confused by the random letters that will appear when they accidentally touch the YubiKey.

Exception: LastPass supports OTP and TOTP as a two factor method and does not support U2F. If you plan on using OTP with LastPass, you will want to skip this step. If you choose TOTP (README.md#set-up-your-yubikey-at-totp---a-google-authenticator-replacement) and don't set up OTP, I'd suggest you disable OTP.

> ykman mode
Current connection mode is: OTP+U2F+CCID
Supported connections are: OTP, U2F, CCID
> ykman mode "U2F+CCID"
Set mode of YubiKey to U2F+CCID? [y/N]: Y
Mode set! You must remove and re-insert your YubiKey for this change to take
effect.

Remove and re-insert the YubiKey.

> ykman mode
Current connection mode is: U2F+CCID
Supported connections are: OTP, U2F, CCID

Use for Two Factor Authentication / U2F Setup

U2F is the recommended two factor method. It is phishing resistant unlike TOTP/Google Authenticator. It is much harder to compromise than SMS/Voice call methods.

The instructions below are specific to provider, but they are all similar enough.

GitHub

  1. Go to your GitHub Security Settings
  2. Turn on Two-factor Authentication if it's not already enabled. You will need to set up either an SMS or TOTP (Google Authenticator) if it's not.
  3. Under Security keys, choose Register new device`
  4. Type in a name: yourname-yubikey-nano4 or something else that will help you remember the key
  5. Click Add
  6. Follow the instructions on screen - you'll probably need to tap the YubiKey for it to register.

Yubico has more detailed instructions.

Google

  1. Go to your Google Sign-in & Security page
  2. Click Two-step verification and you may be prompted for your password.
  3. Click Add Security Key and follow the on-screen instructions. You may need to tap or touch your YubiKey.

Yubico has a video

Dropbox

  1. Go to your Dropbox Security Settings
  2. Under Security keys, click Add
  3. Follow the on-screen instructions. You'll probably be prompted for your password and touch the YubiKey to complete registration.

Yubico has a video and more detailed instructions

Dashlane, Salesforce, Bitbucket, Gitlab, GOV.UK Verify

Yubico has instructions

YubiKey for GPG keysigning

  1. Install GPG2 if you haven't already

    > brew install gnupg gnupg2

  2. Configure your GPG conf at ~/.gnupg/gpg.conf

    Suggested hardened configuration. Here's the minimum that makes sense:

    use-agent
personal-cipher-preferences AES256 AES192 AES CAST5
personal-digest-preferences SHA512 SHA384 SHA256 SHA224
cert-digest-algo SHA512
default-preference-list SHA512 SHA384 SHA256 SHA224 AES256 AES192 AES CAST5 ZLIB BZIP2 ZIP Uncompressed

  3. Temporarily disable U2F

    NOTE: This seemed not to be an issue with my most recent yubikey.

    Having U2F enabled will result in sharing violations that results in gpg2 not being able to access the YubiKey. You will be able to renable U2F and it won't break any sites you already set up with U2F.

    > ykman mode
Current connection mode is: U2F+CCID
Supported connections are: OTP, U2F, CCID
> ykman mode "CCID"
Set mode of YubiKey to CCID? [y/N]: Y
Mode set! You must remove and re-insert your YubiKey for this change to take effect.
> ykman mode
Current connection mode is: CCID
Supported connections are: OTP, U2F, CCID

  4. Generate Keys

    Note: If you have a YubiKey 4, you should use 4096 as your key length. NEO owners should use 2048 as that is the maximum supported.

    > gpg2 --card-edit

[truncated...]

gpg/card> admin
Admin commands are allowed

gpg/card> generate
Make off-card backup of encryption key? (Y/n) n

[PIN Entry pops up, enter 123456, which is the default pin]

What keysize do you want for the Signature key? (2048) 4096 [YubiKey NEO max is 2048]
[PIN Entry pops up, enter 12345678, which is the default admin pin]
The card will now be re-configured to generate a key of 4096 bits

What keysize do you want for the Encryption key? (2048) 4096 [YubiKey NEO max is 2048]
[PIN Entry pops up, enter 12345678, which is the default admin pin]
The card will now be re-configured to generate a key of 4096 bits

What keysize do you want for the Authentication key? (2048) 4096 [YubiKey NEO max is 2048]
[PIN Entry pops up, enter 12345678, which is the default admin pin]
The card will now be re-configured to generate a key of 4096 bits

Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0)
Key does not expire at all
Is this correct? (y/N) Y

GnuPG needs to construct a user ID to identify your key.

Real name: <YOUR_NAME_HERE>
Email address: <YOUR_EMAIL_HERE>
Comment:
You selected this USER-ID:
    "YOUR_NAME_HERE <YOUR_EMAIL_HERE>"

Change (N)ame, (C)omment, (E)mail or (O)kay/(Q)uit? O

    The YubiKey will flash as it's creating the key. Mine took about 5 minutes. When complete, it will say something like

    gpg: key 00000000 marked as ultimately trusted
public and secret key created and signed.

[truncated...]

    You should change your PIN and Admin PIN. You can do that here with passwd at the gpg/card> prompt:

    > gpg --card-edit

...truncated...

gpg/card> admin
Admin commands are allowed

gpg/card> passwd

1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit

Your selection? 1
[Enter 123456]
[Enter your new PIN]
[Enter your new PIN again]

PIN changed.

1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit

Your selection? 3
[Enter 12345678]
[Enter your new Admin PIN]
[Enter your new Admin PIN again]

PIN changed.

1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit

Your selection? Q

  5. (Optional) Other GPG Setup

    While you're here:

    gpg/card> name
Cardholder's surname: [Your last name]
Cardholder's given name: [Your first name]
[Enter your admin PIN]

gpg/card> sex
Sex ((M)ale, (F)emale or space): [Your gender]

gpg/card> lang
Language preferences: [Your two letter language code, example: en)

    You can see the configuration by typing list on the gpg/card> prompt.

    https://www.yubico.com/support/knowledge-base/categories/articles/use-yubikey-openpgp/

YubiKey for SSH logins

You can generate an SSH key from your PGP key and use it for SSH logins.

  1. Identify your authentication key.

    > gpg2 --card-status | grep Authentication
Authentication key: AAAA BBBB CCCC DDDD EEEE  FFFF GGGG HHHH IIII JJJJ

  2. Generate the SSH key

    Take the last 16 digits and pass them to gpg --export-ssh-key.

    > gpg --export-ssh-key GGGGHHHHIIIIJJJJ
ssh-rsa AAAAG4AFq6wm1eCcRclsVOYcJf8y
...
...
G46wm1eCcRclsVOYcJf8yPr1b+kzUpGQLw==

  3. Copy the public key and add it ~/.ssh/authorized_keys the machine you want to SSH into

  4. Attempt to login to the machine via SSH

YubiKey for PIV

Yubico has a GUI tool called yubikey-piv-manager that can help set up your YubiKey for PIV. While I have a preference for command-line tools, the GUI sets everything up in one click and saves significant hassle.

  1. Install YubiKey PIV Manager

    > brew cask install Caskroom/cask/yubikey-piv-manager

  2. Navigate to Setup for macOS and click yes.

    Choose a 6-8 digit number. Don't use non-numeric characters. Yubikey will be fine, but macOS will not.

    The default settings are fine.

  3. Remove and re-insert your YubiKey.

  4. Pair with macOS

    When you insert your Yubikey, a prompt should appear asking if you would like to pair your smartcard. Click Pair. It will ask for your username and password as well as the pin you just created. It may also ask you for your keychain password - it's the same as your account password.

  5. Login with your YubiKey and PIN

    The next time you login with your YubiKey inserted, macOS should prompt you for your PIN and not a password.

YubiKey for OSX login

Once you have PIV credentials on your YubiKey, macOS should prompt you if you want to use it for login.

TODO: Look into yubiswitch to see how it will lock the screen when the YubiKey is removed.

Set up your YubiKey at TOTP - a Google Authenticator replacement

You can have your YubiKey generate TOTP codes, just like Google Authenticator or Authy.

If you use it as a replacement for Google Authenticator, remember that you'll be unable to get the code if you don't have your YubiKey with you and a computer with ykman or Yubico Authenticator installed or an Android phone with Yubico Authenticator installed.

You can also use both a phone based app and a YubiKey, knowing that either device will generate the same codes and will be able to access your account.

  1. Go to Dropbox Security Settings

  2. Choose to enable two factor.

  3. Select Use a mobile app

  4. Click enter your secret key manually to display a 26 digit long base32 key. Note: The link text will differ by provider. The length of the base32 key may also differ.

  5. (Optional) If you also want to use your phone, you can scan the barcode or type in the code to Google Authenticator.

  6. Copy the key below - don't forget to remove the spaces

    % The `-t` will require a touch inorder for codes to be generated.
% This prevent malware from generating codes without your knowledge.
% YubiKey Neo's do not support this feature. Just remove the `-t` flag.
> ykman oath add -t <SERVICE_NAME> <32 DIGIT BASE32 KEY NO SPACES>
> ykman oath code <SERVICE_NAME>
Touch your YubiKey...
SERVICE_NAME 693720

  7. Repeat for other providers.

    The steps will be similar - the difference will be how to get the manual key instead of the QR code. When the QR code is displayed, there will often be a link to get the code. Here are some examples:

    • Dropbox: Enter your secret key manually
    • Gmail: Can't scan it?
    • Github Enter this text code