OpenPGP smartcards and Gentoo - part 1: hardware

Gnupg is an excellent tool for encryption and signing, however, while breaking encryption or forging signatures of large key size is likely somewhere between painful and impossible even for agencies on significant budget, all this is always only as safe as your private key. Let's insert the obvious semi-relevant xkcd reference here, but someone hacking your computer, installing a keylogger and grabbing the key file is more likely. While there are no preventive measures that work for all conceivable attacks, you can at least make things as hard as possible. Be smart, use a smartcard. You'll get a number of additional bonuses on the way. I'm writing up here my personal experiences, as a kind of guide. Also, I am picking a compromise between ultra-security and convenience. Please do not complain if you find guides on the web on how to do things "better".

The smart cards

Obviously, you will need one or more OpenPGP-compatible smart cards and a reader device. I ordered my cards from kernel concepts since that shop is referred in the GnuPG smartcard howto. These are the cards developed by g10code, which is Werner Koch's company (he is the principal author of GnuPG). The website says "2048bit RSA capable", the text printed on the card says "3072bit RSA capable", but at least the currently sold cards support 4096bit RSA keys just fine. (You will need at least app-crypt/gnupg-2.0.19-r2 for encryption keys bigger than 3072bit, see this link and this portage commit.)

The readers

While the GnuPG smartcard howto provides a list of supported reader devices, that list (and indeed the whole document) is a bit stale. The best source of information that I found was the page on the Debian Wiki; Yutaka Niibe, who edits that page regularly, is also one of the code contributors to the smartcard part of GnuPG. In general there are two types of readers, those with a stand-alone pinpad and those without. The extra pinpad takes care that for normal operations like signing and encryption the pin for unlocking the keys is never entering the computer itself- so without tampering with the reader hardware it is impossible pretty hard to sniff it. I bought a SCM SPG532 reader, one of the devices supported ever first by GnuPG, however it's not produced anymore and you may have to resort to newer models soon.

Drivers and software

Now, you'll want to activate the USE flag "smartcard" and maybe "pkcs11", and rebuild app-crypt/gnupg. Afterwards, you may want to log out and back in again, since you may need the gpg-agent from the new emerge.
Several different standards for card reader access exist. One particular is the USB standard for integrated circuit card interface devices, short CCID; the driver for that one is directly built into GnuPG, and the SCM SPG532 is such a device. Another set of drivers is provided by sys-apps/pcsc-lite; that will be used by GnuPG if the built-in stuff fails, but requires a daemon to be running (pcscd, just add it to the default runlevel and start it). The page on the Debian Wiki also lists the required drivers.
These drivers do not need much (or any) configuration, but should work in principle out of the box. Testing is easy, plug in the reader, insert a card, and issue the command

gpg --card-status

If it works, you should see a message about (among other things) manufacturer and serial number of your card. Otherwise, you'll just get an uninformative error. The first thing to check is then (especially for CCID) if the device permissions are OK; just repeat above test as root. If you can now see your card, you know you have permission trouble.
Fiddling with the device file permissions was a serious pain, since all online docs are hopelessly outdated. Please forget about the files linked in the GnuPG smartcard howto. (One cannot be found anymore, the other does not work alone and tries to do things in unnecessarily complicated ways.) At some point in time I just gave up on things like user groups and told udev to hardwire the device to my user account: I created the following file into /etc/udev/rules.d/gnupg-ccid.rules:

ACTION=="add", SUBSYSTEM=="usb", ENV{PRODUCT}=="4e6/e003/*", OWNER:="huettel", MODE:="600"
ACTION=="add", SUBSYSTEM=="usb", ENV{PRODUCT}=="4e6/5115/*", OWNER:="huettel", MODE:="600"

With similar settings it should in principle be possible to solve all the permission problems. (You may want to change the USB id's and the OWNER for your needs.) Then, a quick

udevadm control --reload-rules

followed by unplugging and re-plugging the reader. Now you should be able to check the contents of your card.
If you still have problems, check the following: for accessing the cards, GnuPG starts a background process, the smart card daemon (scdaemon). scdaemon tends to hang every now and then after removing a card. Just kill it (you need SIGKILL)

killall -9 scdaemon

and try again accessing the card afterwards; the daemon is re-started by gnupg. A lot of improvements in smart card handling are scheduled for gnupg-2.0.20; I hope this will be fixed as well.
Here's how a successful card status command looks like on a blank card:

huettel@pinacolada ~ $ gpg --card-status
Application ID ...: D276000124010200000500000AFA0000
Version ..........: 2.0
Manufacturer .....: ZeitControl
Serial number ....: 00000AFA
Name of cardholder: [not set]
Language prefs ...: de
Sex ..............: unspecified
URL of public key : [not set]
Login data .......: [not set]
Signature PIN ....: forced
Key attributes ...: 2048R 2048R 2048R
Max. PIN lengths .: 32 32 32
PIN retry counter : 3 0 3
Signature counter : 0
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]
huettel@pinacolada ~ $

That's it for now, part 2 will be about setting up the basic card data and gnupg functions, then we'll eventually proceed to ssh and pam...

Edit: You can find part 2 here.