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.

Continue reading Offline GnuPG Master Key and Subkeys on YubiKey NEO Smartcard

OpenPGP Key Transition Statement

I have created a new OpenPGP key 54265e8c and will be transitioning away from my old key. If you have signed my old key, I would appreciate signatures on my new key as well. I have created a transition statement that can be downloaded from https://josefsson.org/key-transition-2014-06-22.txt.

Below is the signed statement.

-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA512

OpenPGP Key Transition Statement for Simon Josefsson

I have created a new OpenPGP key and will be transitioning away from
my old key.  The old key has not been compromised and will continue to
be valid for some time, but I prefer all future correspondence to be
encrypted to the new key, and will be making signatures with the new
key going forward.

I would like this new key to be re-integrated into the web of trust.
This message is signed by both keys to certify the transition.  My new
and old keys are signed by each other.  If you have signed my old key,
I would appreciate signatures on my new key as well, provided that
your signing policy permits that without re-authenticating me.

The old key, which I am transitioning away from, is:

pub   1280R/B565716F 2002-05-05
      Key fingerprint = 0424 D4EE 81A0 E3D1 19C6  F835 EDA2 1E94 B565 716F

The new key, to which I am transitioning, is:

pub   3744R/54265E8C 2014-06-22
      Key fingerprint = 9AA9 BDB1 1BB1 B99A 2128  5A33 0664 A769 5426 5E8C

The entire key may be downloaded from: https://josefsson.org/54265e8c.txt

To fetch the full new key from a public key server using GnuPG, run:

  gpg --keyserver keys.gnupg.net --recv-key 54265e8c

If you already know my old key, you can now verify that the new key is
signed by the old one:

  gpg --check-sigs 54265e8c

If you are satisfied that you've got the right key, and the User IDs
match what you expect, I would appreciate it if you would sign my key:

  gpg --sign-key 54265e8c

You can upload your signatures to a public keyserver directly:

  gpg --keyserver keys.gnupg.net --send-key 54265e8c

Or email simon@josefsson.org (possibly encrypted) the output from:

  gpg --armor --export 54265e8c

If you'd like any further verification or have any questions about the
transition please contact me directly.

To verify the integrity of this statement:

  wget -q -O- https://josefsson.org/key-transition-2014-06-22.txt|gpg --verify

/Simon
-----BEGIN PGP SIGNATURE-----
Version: GnuPG v1.4.12 (GNU/Linux)
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=ZaqY
-----END PGP SIGNATURE-----

Creating a small JPEG photo for your OpenPGP key

I’m in the process of moving to a new OpenPGP key, and I want to include a small JPEG image of myself in it. The OpenPGP specification describes, in section 5.12.1 of RFC 4880, how an OpenPGP packet can contain an JPEG image. Unfortunately the document does not require or suggest any properties of images, nor does it warn about excessively large images. The GnuPG manual helpfully asserts that “Note that a very large JPEG will make for a very large key.”.

Researching this further, it seems that proprietary PGP program suggests 120×144 as the maximum size, although I haven’t found an authoritative source of that information. Looking at the GnuPG code, you can see that it suggests around 240×288 in a string saying “Keeping the image close to 240×288 is a good size to use”. Further, there is a warning displayed if the image is above 6144 bytes saying that “This JPEG is really large”.

I think the 6kb warning point is on the low side today, however without any more researched recommendation of image size, I’m inclined to go for a 6kb 240×288 image. Achieving this was not trivial, I ended up using GIMP to crop an image, resize it to 240×288, and then export it to JPEG. Chosing the relevant parameters during export is the tricky part. First, make sure to select ‘Show preview in image window’ so that you get a file size estimate and a preview of how the photo will look. I found the following settings useful for reducing size:

  • Disable “Save EXIF data”
  • Disable “Save thumbnail”
  • Disable “Save XMP data”
  • Change “Subsampling” from the default “4:4:4 (best quality)” to “4:2:0 (chroma quartered)”.
  • Try enabling only one of “Optimize” and “Progressive”. Sometimes I get best results disabling one and keeping the other enabled, and sometimes the other way around. I have not seen smaller size with both enabled, nor with both disabled.
  • Smooth the picture a bit to reduce pixel effects and size.
  • Change quality setting, I had to reduce it to around 25%.

See screenshot below of the settings windows.

GnuPG photo GIMP settings window

Eventually, I managed to get a photo that I was reasonable happy with. It is 240×288 and is 6048 bytes large.

GnuPG photo for Simon

If anyone has further information, or opinions, on what image sizes makes sense for OpenPGP photos, let me know. Ideas on how to reduce size of JPEG images further without reducing quality as much would be welcome.

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.

Continue reading Unattended SSH with Smartcard

EnigForm – HTML/HTTP forms with OpenPGP

Talking to Buanzo, I have been testing the EnigForm plugin for Mozilla. Briefly, EnigForm gives you OpenPGP signing of HTML forms, based on GnuPG, by setting some HTTP headers with the OpenPGP data. This is quite cool, I imagine two use-cases:

  • PGP-based web-authentication. Type your username, have a hidden form field with a nonce, and have EnigForm sign the data. The server verifies the signature, and you have been logged on.
  • PGP-protected web-based forums, bug-tracking systems, polls, etc. What you write in a HTML form is signed by EnigForm, and the server knows who wrote it, and there is persistent evidence of it. Imagine Debian votes through the web instead of via e-mail!

I think this should be documented and forwarded to the IETF for standardization. It is a good example of a simple invention that uses two existing techniques in a new way.