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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Redmine on Debian Lenny Using Lighttpd

The GnuTLS trac installation is in a poor shape. To fix that, I looked into alternatives and found Redmine. Redmine appears to do most things that I liked in Trac (wiki, roadmap and issue tracking) plus it supports more than one project (would come in handy for my other projects) and has built-in git support. I would like to see better spam handling and OpenID support, but it is good enough for our purposes now, and there are similar concerns with trac.

However, getting it up and running with lighttpd on a modern debian lenny installation was not trivial, and I needed some help from #redmine (thanks stbuehler). After finally getting it up and running, I made a copy of the machine using rsync and rsnapshot, so I could re-create a working configuration if I get stuck, and then re-installed the virtual machine.

The notes below are the steps required to set up Redmine using Lighttpd and MySQL on a Debian Lenny. I’m posting this to help others searching for the error messages I got, and to help my own memory in case I need to re-install the server sometime.
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