Offline GnuPG Master Key and Subkeys on YubiKey NEO Smartcard

I have moved to a new OpenPGP key. There are many tutorials and blog posts on GnuPG key generation around, but none of them matched exactly the setup I wanted to have. So I wrote down the steps I took, to remember them if I need to in the future. Briefly my requirements were as follows:

  • The new master GnuPG key is on an USB stick.
  • The USB stick is only ever used on an offline computer.
  • There are subkeys stored on a YubiKey NEO smartcard for daily use.
  • I want to generate the subkeys using GnuPG so I have a backup.
  • Some non-default hash/cipher preferences encoded into the public key.

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Unattended SSH with Smartcard

I have several backup servers that run the excellent rsnapshot software, which uses Secure Shell (SSH) for remote access. The SSH private key of the backup server can be a weak link in the overall security. To see how it can be a problem, consider if someone breaks into your backup server and manages to copy your SSH private key, they will now have the ability to login to all machines that you take backups off (and that should be all of your machines, right?).

The traditional way to mitigate SSH private key theft is by password protecting the private key. This works poorly in an unattended server environment because either the decryption password needs to be stored in disk (where the attacker can read it) or the decrypted private key has to be available in decrypted form in memory (where attacker can read it).

A better way to deal with the problem is to move the SSH private key to a smartcard. The idea is that the private key cannot be copied by an attacker who roots your backup server. (Careful readers may have spotted a flaw here, and I need to explain one weakness with my solution: an attacker will still be able to login to all your systems by going through your backup server, however it will require an open inbound network connection to your backup server and the attacker will never know what your private key is. What this does is to allow you to more easily do damage control by removing the smartcard from the backup server.)

In this writeup, I’ll explain how to accomplish all this on a Debian/Ubuntu-system using a OpenPGP smartcard, a Gemalto USB Shell Token v2 with gpg-agent/scdaemon from GnuPG together with OpenSSH.

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