Setting up your YubiKey for challenge response authentication on Max OS X

This article explains the process to get the challenge-response authentication possible with newer YubiKeys working on Mac OS X. Since Mac OS X uses PAM like most other Unix/POSIX systems do, most of this should apply to other operating systems, too.

Getting yubico-pam

First you will have to install yubico-pam and its dependencies required for challenge-response authentication. Use your distribution’s package manager to get it, or build from source. If you’re on OS X you can use MacPorts to install yubico-pam:

sudo port install yubico-pam
This will probably not work in non-superuser installations of MacPorts, because it needs to place the yubico PAM module into /usr/lib/pam.

Configuring your YubiKey

The next step would be to set up your YubiKey for challenge-response authentication, if you haven’t done so already. Although this is possible with the command line ykpersonalize tool, the GUI "YubiKey Personalization Tool" is a more comfortable way to do this.

  1. Plug in your YubiKey and start the YubiKey Personalization Tool

    YubiKey Personalization Tool shows whether your YubiKey supports challenge-response in the lower right. 2. Click Challenge-Response 3. Select HMAC-SHA1 mode. Apparently Yubico-OTP mode doesn’t work with yubico-pam at the moment. 4. Select the configuration slot you want to use (this text assumes slot two, but it should be easy enough to adapt the instructions if you prefer slot 1) 5. Select whether you want to require pressing the button for authentication
    If you enable this, you will have to press the button twice for each authentication with yubico-pam. This is because the PAM module does not only send the challenge on file and checks whether the response matches, but also generates a new challenge-response pair on success. 6. Use Variable input as HMAC-SHA1 mode
    Using Fixed 64 byte input for this value made my YubiKey always return the same response regardless of what the challenge was. Since this defies the purpose of challenge-response think twice and test before you use this! 7. Generate a secret key You won’t need this key again, it’s sufficient to have it on your YubiKey. Note that the YubiKey Personalization Tool by default logs the key to configuration_log.csv in your home directory. Consider turning this off in the settings before writing or shredding the file after writing. 8. Click Write Configuration

Configuring your user account to accept the YubiKey

After setting up your YubiKey you need to configure your account to accept this YubiKey for authentication. To do this, open a terminal and run

create the directory where ykpamcfg will store the initial challenge
mkdir -m0700 -p ~/.yubico
get the initial challenge from the YubiKey
ykpamcfg -2

If you used slot 1 above, replace -2 with -1. If you configured your YubiKey to require a button press the LED on the YubiKey will start blinking; press the button to send a challenge-response response. ykpamcfg should finish successfully telling you that it stored the initial challenge somewhere inside your home directory:

Stored initial challenge and expected response in '/path/to/your/home/.yubico/challenge-KEYID'.

This step will create a file with a challenge and the expected response (that can only be generated with the secret key
[This is also the reason why you should avoid having copies of the key in other places than your YubiKey!]
) in your home directory. The PAM module will later open this file, read the challenge, send it to the connected YubiKey and check whether its answer matches the one on file. If it does, it generates a new challenge, asks the YubiKey for the correct response for this challenge and writes both into the file. This also means that you need to keep this file secure from other users (which is why we created the .yubico directory in your home with mode 0700).

Configuring your system to use Yubico PAM for authentication

Linux, Solaris, OS X and most BSD variants use the Pluggable Authentication Modules (PAM) framework to handle authentication. Using PAM you can specify which modules are used for authentication of users and which of them are required, optional and/or sufficient to authenticate a user. Using PAM you can for example set up multiple-factor authentication, by chaining multiple required modules.

PAM is configured through files in /etc/pam.d on most systems. Each file in this directory is used for a specific service, i.e. the file /etc/pam.d/sudo is used to authenticate users for the sudo program. Debian, for example, uses include directives in these files to have a central place to configure authentication; in this case we are not using this on purpose, because challenge-response authentication doesn’t work remotely (e.g. via SSH), so we only want to configure it for services we use when on site.

The file format in these files is documented in man 5 pam.conf; it looks like this:

function-class control-flag module-path arguments



is one of auth, account, session, and password. Since we only care about authentication with the YubiKey and yubico-pam only handles authentication, we will always be using auth here.


is one of required, sufficient, optional and some other values depending on your PAM implementation. If we want to make YubiKey challenge-response mandatory but combined with other methods (e.g. password), we can use required, if we want successful challenge-response to be enough to authenticate a user, we can use sufficient. optional is not of any use for us in this case.


selects the module to be used for this authentication step. This is used as filename in a directory where pam libraries are expected, on OS X e.g. /usr/lib/pam, /usr/lib/security on some other systems. We want in this case, which will load /usr/lib/pam/


are passed to the pam module and can be used to configure its behavior. See Supported PAM module parameters in README for a list of possible values. Since we want to use challenge-response, we add mode=challenge-response and to debug the setup initially also debug, separated by spaces. debug can safely be removed later.

If you misconfigure your PAM modules here you might lose your ability to sudo! Always keep a root shell open to be able to revert your changes in case something goes wrong!

So, if we wanted to use the YubiKey to allow us to sudo without typing a password, we would add

auth       sufficient mode=challenge-response debug

To get this working on the loginwindow for local interactive login add the to the pam.d file authorization as the first line. The whole file might look something like this (example taken from OS X):

sudo: auth account password session
auth       sufficient mode=challenge-response debug
auth       required
account    required
password   required
session    required

If we wanted to require successful challenge-response authentication in addition to the usual password, we can change the sufficient in the line we added to required.

In theory you can configure pretty much any service you use locally to use challenge-response authentication. In practice, I had problems configuring challenge-response into the login window of OS X. Keep a rescue disk or a remote root terminal available when attempting such configurations, just in case something goes wrong and you need to restore the PAM configuration to an old state.
On Debian it started working for me after accidentally getting the file-rights correctly. 755 for ~/.yubico & 600 for the files therein. Otherwise the module can’t find, read and/or write to the appropriate files. Your clue is the following debug messages.
[drop_privs.c:restore_privileges(128)] pam_modutil_drop_priv: -1
[pam_yubico.c:do_challenge_response(542)] could not restore privileges
[pam_yubico.c:do_challenge_response(664)] Challenge response failed: No such file or directory