GnuPG notes: subkeys, yubikey, gpg1 vs gpg2

Switching from one GnuPG master key to the usage of subkeys was long on my list of things I wanted to do, but never came around. With the advent of a YubiKey NEO in my pocket I finally took the plunge: reading through lots of web pages (and adding one here for confusion), trying to understand the procedures, and above all, understanding my own requirements!

gpg-subkeys-yubi

To sum up a long story, it was worth the plunge, and all over the security level of my working environment has improved considerable.

While the advantages of subkeys are well documented (e.g., Debian Wiki), at the end of the day I was – like probably many Debian Developers – having one master key that was used for every action: mail decryption and signing, signing of uploads, etc. Traveling a lot I always felt uncomfortable. Despite a lengthy passphrase, I still didn’t want my master key to get into wrong hands in case the laptop got stolen. Furthermore, I had my master key on several computers (work, laptop, mail server), which didn’t help a lot either. With all this, I started to compile a list of requirements/objectives I wanted to have:

  • master key is only available on offline medium (USB sticks)
  • subkeys for signing, encryption, authentication
  • possibility to sign and decrypt my emails on the server where I read emails (ssh/mutt)
  • laptop does not contain any keys, instead use Yubikey
  • all keys with expiry date (1y)
  • mixture of gpg versions: local laptop: gpg2.1, mail server: gpg1

Warning Before we start a word of caution – make backups, best is to make backups at every stage. You don’t want that an erroneous operations wipes out your precious keys without a backup!

Preparation

In the following I will assume that MASTERKEY environment variable contains the id of the master key to be converted. Furthermore, I have followed some of the advice here, so key ids will be shown in long format.

Let us start with the current situation:

$ gpg -K $MASTERKEY
sec   4096R/0x6CACA448860CDC13 2010-09-14
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                            Norbert Preining <norbert@preining.info>
uid                            Norbert Preining <preining@logic.at>
uid                            Norbert Preining <preining@debian.org>
uid                            Norbert Preining <preining@jaist.ac.jp>
ssb   4096R/0xD1D2BD14810F62B3 2010-09-14

In the following we will go through the following steps:

  • Prepare the Yubikey NEO (forthcoming blog>
  • Edit to current key: add expiry, add photo, and above all add subkeys
  • Create revocation certificate
  • Create gpg2.1 structure
  • Backup to USB media
  • Move subkeys to Yubikey NEO
  • Remove master keys
  • Separate gpg1 (for mail server) and gpg2 (for laptop)
  • Upload to key servers

Yubikey SmartCard setup

There are several guides out there, but I will in very near future write one about using the NEO for various usage scenaria including GPG keys.

Edit the current key

The following can be done in one session or in different sessions, the screen logs are after starting with:

$ gpg --expert --edit-key $MASTERKEY

add expiry date

Having an expiry date on your key serves two purposes: If you loose it, it will solve itself automatically, and furthermore, you are forced to deal with the key – and refresh your gpg knowledge – at least once a year. That are two perfect reasons to set expiry to one year.

The following log selects each key in turn and sets its expiry date.

$ gpg --expert --edit-key $MASTERKEY
gpg (GnuPG) 1.4.20; Copyright (C) 2015 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
 
Secret key is available.
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: never       usage: SC  
                               trust: ultimate      validity: ultimate
sub  4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: never       usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
 
gpg> expire
Changing expiration time for the primary key.
Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0) 1y
Key expires at Mon 06 Feb 2017 08:09:16 PM JST
Is this correct? (y/N) y
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub  4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: never       usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
 
gpg> key 1
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: never       usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
 
gpg> expire
Changing expiration time for a subkey.
Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0) 1y
Key expires at Mon 06 Feb 2017 08:09:27 PM JST
Is this correct? (y/N) y
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>

Add a photo

Not strictly necessary, but an interesting feature. gpg suggests 240×288, I resized a photo of my head, greyscaled it, and optimized it with jpegoptim -s -m40 my-photo.jpg. The parameter 40 is the quality, I played around a bit to find the best balance between size and quality. The size should not be too big as the photo will be part of the key!

gpg> addphoto
 
Pick an image to use for your photo ID.  The image must be a JPEG file.
Remember that the image is stored within your public key.  If you use a
very large picture, your key will become very large as well!
Keeping the image close to 240x288 is a good size to use.
 
Enter JPEG filename for photo ID: GPG/norbert-head.jpg
Is this photo correct (y/N/q)? y
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ unknown] (5)  [jpeg image of size 4185]

Add subkeys of 2048bit for signing/encryption/authentication

Now comes the interesting part, adding three subkeys: one for signing, one for encrypting, and one for authentication. The one for signing is the one you will use for signing your uploads to Debian as well as emails. The authentication key will later be used to provide ssh authentication. Note that you have to use the --expert expert option to edit-key (as shown above), otherwise gpg does not allow to do this.

As I want to move the subkeys to the Yubikey NEO, a keysize of 2048bits is necessary.

First for the signing:

gpg> addkey
Key is protected.
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
Please select what kind of key you want:
   (3) DSA (sign only)
   (4) RSA (sign only)
   (5) Elgamal (encrypt only)
   (6) RSA (encrypt only)
   (7) DSA (set your own capabilities)
   (8) RSA (set your own capabilities)
Your selection? 4
RSA keys may be between 1024 and 4096 bits long.
What keysize do you want? (2048) 
Requested keysize is 2048 bits
Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0) 1y
Key expires at Mon 06 Feb 2017 08:10:06 PM JST
Is this correct? (y/N) y
Really create? (y/N) y
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
....+++++
..........+++++
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
sub  2048R/0xEC00B8DAD32266AA  created: 2016-02-07  expires: 2017-02-06  usage: S   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ unknown] (5)  [jpeg image of size 4185]

Now the same for encryption key:

gpg> addkey
Key is protected.
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
Please select what kind of key you want:
   (3) DSA (sign only)
   (4) RSA (sign only)
   (5) Elgamal (encrypt only)
   (6) RSA (encrypt only)
   (7) DSA (set your own capabilities)
   (8) RSA (set your own capabilities)
Your selection? 6
RSA keys may be between 1024 and 4096 bits long.
What keysize do you want? (2048) 
Requested keysize is 2048 bits
Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0) 1y
Key expires at Mon 06 Feb 2017 08:10:20 PM JST
Is this correct? (y/N) y
Really create? (y/N) y
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
..+++++
........+++++
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
sub  2048R/0xEC00B8DAD32266AA  created: 2016-02-07  expires: 2017-02-06  usage: S   
sub  2048R/0xBF361ED434425B4C  created: 2016-02-07  expires: 2017-02-06  usage: E   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ unknown] (5)  [jpeg image of size 4185]

Finally for the authentication key. Note that only here the --expert is necessary! We use ‘(8) RSA (set your own capabilities)’ and then toggle sign and encryption capabilities off, and authentication on.

gpg> addkey
Key is protected.
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
Please select what kind of key you want:
   (3) DSA (sign only)
   (4) RSA (sign only)
   (5) Elgamal (encrypt only)
   (6) RSA (encrypt only)
   (7) DSA (set your own capabilities)
   (8) RSA (set your own capabilities)
Your selection? 8
 
Possible actions for a RSA key: Sign Encrypt Authenticate 
Current allowed actions: Sign Encrypt 
 
   (S) Toggle the sign capability
   (E) Toggle the encrypt capability
   (A) Toggle the authenticate capability
   (Q) Finished
 
Your selection? s
 
Possible actions for a RSA key: Sign Encrypt Authenticate 
Current allowed actions: Encrypt 
 
   (S) Toggle the sign capability
   (E) Toggle the encrypt capability
   (A) Toggle the authenticate capability
   (Q) Finished
 
Your selection? e
 
Possible actions for a RSA key: Sign Encrypt Authenticate 
Current allowed actions: 
 
   (S) Toggle the sign capability
   (E) Toggle the encrypt capability
   (A) Toggle the authenticate capability
   (Q) Finished
 
Your selection? a
 
Possible actions for a RSA key: Sign Encrypt Authenticate 
Current allowed actions: Authenticate 
 
   (S) Toggle the sign capability
   (E) Toggle the encrypt capability
   (A) Toggle the authenticate capability
   (Q) Finished
 
Your selection? q
RSA keys may be between 1024 and 4096 bits long.
What keysize do you want? (2048) 
Requested keysize is 2048 bits
Please specify how long the key should be valid.
         0 = key does not expire
      <n>  = key expires in n days
      <n>w = key expires in n weeks
      <n>m = key expires in n months
      <n>y = key expires in n years
Key is valid for? (0) 1y
Key expires at Mon 06 Feb 2017 08:10:34 PM JST
Is this correct? (y/N) y
Really create? (y/N) y
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
......+++++
+++++
 
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub* 4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
sub  2048R/0xEC00B8DAD32266AA  created: 2016-02-07  expires: 2017-02-06  usage: S   
sub  2048R/0xBF361ED434425B4C  created: 2016-02-07  expires: 2017-02-06  usage: E   
sub  2048R/0x9C7CA4E294F04D49  created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ unknown] (5)  [jpeg image of size 4185]
 
gpg> save

Check the current status

Good point to take a break and inspect the current status. We should have one main key and three subkeys, all with expiry dates of 1 year ahead, and a photo also attached to the key:

$ gpg --expert --edit-key $MASTERKEY
gpg (GnuPG) 1.4.20; Copyright (C) 2015 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
 
Secret key is available.
 
gpg: checking the trustdb
gpg: public key 0x0FC3EC02FBBB8AB1 is 58138 seconds newer than the signature
gpg: 3 marginal(s) needed, 1 complete(s) needed, classic trust model
gpg: depth: 0  valid:   2  signed:  28  trust: 0-, 0q, 0n, 0m, 0f, 2u
gpg: depth: 1  valid:  28  signed:  41  trust: 28-, 0q, 0n, 0m, 0f, 0u
gpg: next trustdb check due at 2016-11-02
pub  4096R/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06  usage: SC  
                               trust: ultimate      validity: ultimate
sub  4096R/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06  usage: E   
sub  2048R/0xEC00B8DAD32266AA  created: 2016-02-07  expires: 2017-02-06  usage: S   
sub  2048R/0xBF361ED434425B4C  created: 2016-02-07  expires: 2017-02-06  usage: E   
sub  2048R/0x9C7CA4E294F04D49  created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg>

Create revocation certificate

In case something happens, like all your backups are burned, your computers are destroyed, or all data stolen by the NSA, it is a good idea to have an old fashioned paper print out of a revocation certificate which allows you to revoke the key even if you are not in possession of it.

This should be printed out and kept in a safe place.

$ gpg --gen-revoke $MASTERKEY > GPG/revoke-certificate-$MASTERKEY.txt
 
sec  4096R/0x6CACA448860CDC13 2010-09-14 Norbert Preining <norbert@preining.info>
 
Create a revocation certificate for this key? (y/N) y
Please select the reason for the revocation:
  0 = No reason specified
  1 = Key has been compromised
  2 = Key is superseded
  3 = Key is no longer used
  Q = Cancel
(Probably you want to select 1 here)
Your decision? 1
Enter an optional description; end it with an empty line:
> 
Reason for revocation: Key has been compromised
(No description given)
Is this okay? (y/N) y
 
You need a passphrase to unlock the secret key for
user: "Norbert Preining <norbert@preining.info>"
4096-bit RSA key, ID 0x6CACA448860CDC13, created 2010-09-14
 
Enter passphrase:
 
ASCII armored output forced.
Revocation certificate created.

Please move it to a medium which you can hide away; if the NSA or KGB or Mossad gets access to this certificate, they can use it to make your key unusable. It is smart to print this certificate and store it away, just in case your media become unreadable.

Create gpg 2.1 structure

There are currently three versions of gpg available: ‘classic’ (version 1) which is one static binary, perfect for servers or scripting tasks; ‘stable’ (version 2.0) which is the modularized version supporting OpenPGP, S/MIME, and Secure Shell; and finally ‘modern’ (version 2.1 and up) with enhanced features like support for Elliptic Curve cryptography. Debian currently ships version 1 as standard, and also the modern version (but there are traces in experimental of a pending transition).

The newer versions of GnuPG are modularized and use an agent. For the following we need to kill any running instance of gpg-agent.

$ killall gpg-agent

After that a simple call to gpg2 to list the secret keys will convert the layout to the new standard:

$ gpg2 -K $MASTERKEY
gpg: keyserver option 'ca-cert-file' is obsolete; please use 'hkp-cacert' in dirmngr.conf
gpg: starting migration from earlier GnuPG versions
gpg: porting secret keys from '/home/norbert/.gnupg/secring.gpg' to gpg-agent
gpg: key 0xD2BF4AA309C5B094: secret key imported
gpg: key 0x6CACA448860CDC13: secret key imported
gpg: migration succeeded
sec   rsa4096/0x6CACA448860CDC13 2010-09-14 [SC] [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                   [ultimate] Norbert Preining <norbert@preining.info>
uid                   [ultimate] Norbert Preining <preining@logic.at>
uid                   [ultimate] Norbert Preining <preining@debian.org>
uid                   [ultimate] Norbert Preining <preining@jaist.ac.jp>
uid                   [ultimate] [jpeg image of size 4185]
ssb   rsa4096/0xD1D2BD14810F62B3 2010-09-14 [E] [expires: 2017-02-06]
ssb   rsa2048/0xEC00B8DAD32266AA 2016-02-07 [S] [expires: 2017-02-06]
ssb   rsa2048/0xBF361ED434425B4C 2016-02-07 [E] [expires: 2017-02-06]
ssb   rsa2048/0x9C7CA4E294F04D49 2016-02-07 [A] [expires: 2017-02-06]

After this there will be new files/directories in the .gnupg directory, in particular: .gnupg/private-keys-v1.d/ which contains the private keys.

Creating backup

Now your .gnupg directory contains still all the keys, available for gpg1 and gpg2.1.

You MUST MAKE A BACKUP NOW!!! on at least 3 USB sticks and maybe some other offline media. Keep them in a safe place, better in different and safe places, you will need them for extending the expiry date, signing other keys, etc.

Warning concerning USB and vfat file systems

gpg >= 2.1 requires gpg-agent which in turn needs a socket. If you have the backup on an USB drive (most often with vfat file system), you need to redirect the socket, as vfat does not support sockets!

Edit /USBSTICK/gnupghome/S.gpg-agent and enter there

%Assuan%
socket=/dev/shm/S.gpg-agent

After that the socket will be created in /dev/shm/ instead and invoking gpg with gpg2 --homedir /USBSTICK/gnupghome will work.

You have done your backups, right?

Move sub keys to card

As I mentioned, I want to have no keys on my laptop which I carry around to strange countries, instead I want to have them all on a Yubikey NEO. I will describe the setup and usage in details soon, but mention here only how to move the keys to the card. This requires a finished setup including change of pins.

Note that when using gpg2 to move the keys to the card, the local copies are actually deleted, but only for the gpg2(.1) files. The gpg1 secret keys are still all in place.

$ gpg2 --edit-key $MASTERKEY
gpg (GnuPG) 2.1.11; Copyright (C) 2016 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
 
Secret key is available.
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 2
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb* rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> keytocard
Please select where to store the key:
   (1) Signature key
   (3) Authentication key
Your selection? 1
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb* rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 2
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 3
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb* rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> keytocard
Please select where to store the key:
   (2) Encryption key
Your selection? 2
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb* rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 3
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 4
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb* rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> keytocard
Please select where to store the key:
   (3) Authentication key
Your selection? 3
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb* rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> key 4
 
sec  rsa4096/0x6CACA448860CDC13
     created: 2010-09-14  expires: 2017-02-06  usage: SC  
     trust: ultimate      validity: ultimate
ssb  rsa4096/0xD1D2BD14810F62B3
     created: 2010-09-14  expires: 2017-02-06  usage: E   
ssb  rsa2048/0xEC00B8DAD32266AA
     created: 2016-02-07  expires: 2017-02-06  usage: S   
ssb  rsa2048/0xBF361ED434425B4C
     created: 2016-02-07  expires: 2017-02-06  usage: E   
ssb  rsa2048/0x9C7CA4E294F04D49
     created: 2016-02-07  expires: 2017-02-06  usage: A   
[ultimate] (1). Norbert Preining <norbert@preining.info>
[ultimate] (2)  Norbert Preining <preining@logic.at>
[ultimate] (3)  Norbert Preining <preining@debian.org>
[ultimate] (4)  Norbert Preining <preining@jaist.ac.jp>
[ultimate] (5)  [jpeg image of size 4185]
 
gpg> save

Note the repetition of selecting and deselecting keys.

Current status

After this procedure we are now in the following situation:

  • gpg1: all keys are still available
  • gpg2: sub keys are moved to yubikey (indicated below by ssb>), and master key is still available

In gpg words it looks like this:

$ gpg2 -K $MASTERKEY
gpg: keyserver option 'ca-cert-file' is obsolete; please use 'hkp-cacert' in dirmngr.conf
sec   rsa4096/0x6CACA448860CDC13 2010-09-14 [SC] [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                   [ultimate] Norbert Preining <norbert@preining.info>
uid                   [ultimate] Norbert Preining <preining@logic.at>
uid                   [ultimate] Norbert Preining <preining@debian.org>
uid                   [ultimate] Norbert Preining <preining@jaist.ac.jp>
uid                   [ultimate] [jpeg image of size 4185]
ssb   rsa4096/0xD1D2BD14810F62B3 2010-09-14 [E] [expires: 2017-02-06]
ssb>  rsa2048/0xEC00B8DAD32266AA 2016-02-07 [S] [expires: 2017-02-06]
ssb>  rsa2048/0xBF361ED434425B4C 2016-02-07 [E] [expires: 2017-02-06]
ssb>  rsa2048/0x9C7CA4E294F04D49 2016-02-07 [A] [expires: 2017-02-06]
 
$ gpg -K $MASTERKEY
sec   4096R/0x6CACA448860CDC13 2010-09-14 [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                            Norbert Preining <norbert@preining.info>
uid                            Norbert Preining <preining@logic.at>
uid                            Norbert Preining <preining@debian.org>
uid                            Norbert Preining <preining@jaist.ac.jp>
uid                            [jpeg image of size 4185]
ssb   4096R/0xD1D2BD14810F62B3 2010-09-14 [expires: 2017-02-06]
ssb   2048R/0xEC00B8DAD32266AA 2016-02-07 [expires: 2017-02-06]
ssb   2048R/0xBF361ED434425B4C 2016-02-07 [expires: 2017-02-06]
ssb   2048R/0x9C7CA4E294F04D49 2016-02-07 [expires: 2017-02-06]
 
$ gpg2 --card-status
 
....
Name of cardholder: Norbert Preining
....
PIN retry counter : 3 3 3
Signature counter : 0
Signature key ....: 5871 F824 2DCC 3660 2362  BE7D EC00 B8DA D322 66AA
      created ....: 2016-02-07 11:10:06
Encryption key....: 2501 195C 90AB F4D2 3DEA  A303 BF36 1ED4 3442 5B4C
      created ....: 2016-02-07 11:10:20
Authentication key: 9CFB 3775 C164 0E99 F0C8  014C 9C7C A4E2 94F0 4D49
      created ....: 2016-02-07 11:10:34
General key info..: sub  rsa2048/0xEC00B8DAD32266AA 2016-02-07 Norbert Preining <norbert@preining.info>
sec   rsa4096/0x6CACA448860CDC13  created: 2010-09-14  expires: 2017-02-06
ssb   rsa4096/0xD1D2BD14810F62B3  created: 2010-09-14  expires: 2017-02-06
ssb>  rsa2048/0xEC00B8DAD32266AA  created: 2016-02-07  expires: 2017-02-06
                                  card-no: 0006 03645719
ssb>  rsa2048/0xBF361ED434425B4C  created: 2016-02-07  expires: 2017-02-06
                                  card-no: 0006 03645719
ssb>  rsa2048/0x9C7CA4E294F04D49  created: 2016-02-07  expires: 2017-02-06
                                  card-no: 0006 03645719
$

Remove private master keys

You are sure that you have a working backup? Did you try it with gpg --homedir ...? Only if you are really sure, continue.

We are now removing the master key from both the gpg2 and gpg1 setup.

removal for gpg2

gpg2 keeps the private keys in ~/.gnupg/private-keys-v1.d/KEYGRIP.key and the KEYGRIP can be found by adding --with-keygrip to the key listing. Be sure to delete the correct file, the one related to the master key.

$ gpg2 --with-keygrip --list-key $MASTERKEY
pub   rsa4096/0x6CACA448860CDC13 2010-09-14 [SC] [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
      Keygrip = 9DC1E90703856C1DE0EAC970CED7ABF5EE5EF79D
uid                   [ultimate] Norbert Preining <norbert@preining.info>
uid                   [ultimate] Norbert Preining <preining@logic.at>
uid                   [ultimate] Norbert Preining <preining@debian.org>
uid                   [ultimate] Norbert Preining <preining@jaist.ac.jp>
uid                   [ultimate] [jpeg image of size 4185]
sub   rsa4096/0xD1D2BD14810F62B3 2010-09-14 [E] [expires: 2017-02-06]
      Keygrip = 4B8FF57434DD989243666377376903281D861596
sub   rsa2048/0xEC00B8DAD32266AA 2016-02-07 [S] [expires: 2017-02-06]
      Keygrip = 39B14EF1392F2F251863A87AE4D44CE502755C39
sub   rsa2048/0xBF361ED434425B4C 2016-02-07 [E] [expires: 2017-02-06]
      Keygrip = E41C8DDB2A22976AE0DA8D7D11F586EA793203EA
sub   rsa2048/0x9C7CA4E294F04D49 2016-02-07 [A] [expires: 2017-02-06]
      Keygrip = A337DE390143074C6DBFEA64224359B9859B02FC
 
$ rm ~/.gnupg/private-keys-v1.d/9DC1E90703856C1DE0EAC970CED7ABF5EE5EF79D.key
$

After that the missing key is shown in gpg2 -K with an additional # meaning that the key is not available:

$ gpg2 -K $MASTERKEY
sec#  rsa4096/0x6CACA448860CDC13 2010-09-14 [SC] [expires: 2017-02-06]
...
removal for gpg1

Up to gpg v2.0 there is no simple way to delete only one part of the key. We export the subkeys, delete the private key, and reimport the subkeys:

$ gpg --output secret-subkeys --export-secret-subkeys $MASTERKEY
 
$ gpg --delete-secret-keys $MASTERKEY
 
sec  4096R/0x6CACA448860CDC13 2010-09-14 Norbert Preining <norbert@preining.info>
 
Delete this key from the keyring? (y/N) y
This is a secret key! - really delete? (y/N) y
 
$ gpg --import secret-subkeys
gpg: key 0x6CACA448860CDC13: secret key imported
gpg: key 0x6CACA448860CDC13: "Norbert Preining <norbert@preining.info>" not changed
gpg: Total number processed: 1
gpg:              unchanged: 1
gpg:       secret keys read: 1
gpg:   secret keys imported: 1
 
$

Current status

We are basically at the stage we wanted to achieve:

For gpg2.1 only the old encryption key is available, the master key is not, and the other sub keys are moved to the yubikey:

$ gpg2 -K $MASTERKEY
sec#  rsa4096/0x6CACA448860CDC13 2010-09-14 [SC] [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                   [ultimate] Norbert Preining <norbert@preining.info>
uid                   [ultimate] Norbert Preining <preining@logic.at>
uid                   [ultimate] Norbert Preining <preining@debian.org>
uid                   [ultimate] Norbert Preining <preining@jaist.ac.jp>
uid                   [ultimate] [jpeg image of size 4185]
ssb   rsa4096/0xD1D2BD14810F62B3 2010-09-14 [E] [expires: 2017-02-06]
ssb>  rsa2048/0xEC00B8DAD32266AA 2016-02-07 [S] [expires: 2017-02-06]
ssb>  rsa2048/0xBF361ED434425B4C 2016-02-07 [E] [expires: 2017-02-06]
ssb>  rsa2048/0x9C7CA4E294F04D49 2016-02-07 [A] [expires: 2017-02-06]
$

And for gpg <= 2.0 the old encryption key and the sub keys are available, but the master key is not:

$ gpg -K $MASTERKEY
sec#  4096R/0x6CACA448860CDC13 2010-09-14 [expires: 2017-02-06]
      Key fingerprint = F7D8 A928 26E3 16A1 9FA0  ACF0 6CAC A448 860C DC13
uid                            Norbert Preining <norbert@preining.info>
uid                            Norbert Preining <preining@logic.at>
uid                            Norbert Preining <preining@debian.org>
uid                            Norbert Preining <preining@jaist.ac.jp>
uid                            [jpeg image of size 4185]
ssb   4096R/0xD1D2BD14810F62B3 2010-09-14 [expires: 2017-02-06]
ssb   2048R/0xEC00B8DAD32266AA 2016-02-07 [expires: 2017-02-06]
ssb   2048R/0xBF361ED434425B4C 2016-02-07 [expires: 2017-02-06]
ssb   2048R/0x9C7CA4E294F04D49 2016-02-07 [expires: 2017-02-06]
 
$

Split the .gnupg directory for mail server and laptop

As mentioned, I want to have a gpg1 version available at the server where I read my emails, and be able to sign/encrypt emails there, while on my laptop no secret key is available. Thus I prepare two gnupg directories.

For the mailserver the gpg2 specific files are removed:

$ cp -a .gnupg .gnupg-mail
$ cd .gnupg-mail
$ rm -rf private-keys-v1.d/ pubring.gpg~ reader_0.status
$ rm -rf S.gpg-agent* S.scdaemon .gpg-v21-migrated

On my laptop, where I did all this operation, I remove the gpg1 files, namely the outdated secring.gpg:

$ cd $HOME/.gnupg
$ rm secring.gpg

As a last step I move the .gnupg-mail directory to my mail server.

Once could *expire* the old encryption key, but for now I leave it as is.

Upload keys to keyservers

If you are a Debian Developer, a simple update of your master key will suffice:

gpg --keyserver hkp://keyring.debian.org --send-key YOURMASTERKEYID

Note that the update from the keyring server to the actual Debian keyring takes up to one month. Until that time either do not upload anything, or use the (offline) master key for signing. After your key has been updated in the Debian keyring, signatures made with the signing subkey will be accepted for uploading to Debian.

It might be also a good idea to upload your new keys to some keyservers like:

gpg --keyserver hkp://pool.sks-keyservers.net --send-key $MASTERKEY

Now you an also fix the configuration file skew between gpg1 and gpg2.

Further remark

I am currently trying to use the authentication key from my Yubikey NEO as ssh key, but bugs (see #795368 and #818969) prohibit it at the moment. Raphael Herzog gave a possible fix by killing the gpg-agent and restarting it with gpg-agent --daemon from an X terminal, and I can confirm that this worked.

After one year before the key expires I need to extend the key validity for another year. For this you need the offline master key. I will describe the process when it becomes necessary.

Reading list

The following web sites have been useful in collecting the necessary information:

  1. https://iain.learmonth.me/yubikey-neo-gpg/
  2. https://iain.learmonth.me/yubikey-udev/
  3. http://blog.josefsson.org/2014/06/23/offline-gnupg-master-key-and-subkeys-on-yubikey-neo-smartcard/
  4. https://wiki.debian.org/Subkeys
  5. https://jclement.ca/articles/2015/gpg-smartcard/ as modernized version of (3)
  6. https://www.esev.com/blog/post/2015-01-pgp-ssh-key-on-yubikey-neo/ similar style, with ssh and gnome-keyring infos
  7. http://karlgrz.com/2fa-gpg-ssh-keys-with-pass-and-yubikey-neo/ also good reading
  8. https://help.riseup.net/en/security/message-security/openpgp/best-practices good and concise advise on gpg practices

My writing is mostly based on (5) with additions from (4).

Please let me know of any errors, improvements, and fixes. I hope this walk-through might help others in the same situation.

6 Responses

  1. mirabilos says:

    You’ll also want the -s option to jpegoptim, which removes all metadata (EXIF, etc.)

  2. Sam says:

    Why are there two subkeys that are assigned encryption abilities ? This makes things more cumbersome, without adding any additional security. No?
    Also, this article is most excellent. It is one of the handful of gpg articles that proved helpful to me, a newer user of GPG 2.2. Thanks!

    • The one key is the master key with 4096bits, and is generated automatically when you create the main key. I am not sure whether you can revoke/remove that one safely. The other is the sub key that goes on the yubikey, or be used on your computer with the main key offline.

  1. 2016/04/23
  2. 2016/05/07

    […] there are loads of guides (see the previous article on GnuPG for some of them), many of them are out-of-date for current distributions and GnuPG etc. So I tried […]

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