Category Archives: debian

On language bindings & Relaunching Guile-GnuTLS

Posted on by

The Guile bindings for GnuTLS has been part of GnuTLS since spring 2007 when Ludovic Courtès contributed it after some initial discussion. I have been looking into getting back to do GnuTLS coding, and during a recent GnuTLS meeting one topic was Guile bindings. It seemed like a fairly self-contained project to pick up on. It is interesting to re-read the old thread when this work was included: some of the concerns brought up there now have track record to be evaluated on. My opinion that the cost of introducing a new project per language binding today is smaller than the cost of maintaining language bindings as part of the core project. I believe the cost/benefit ratio has changed during the past 15 years: introducing a new project used to come with a significant cost but this is no longer the case, as tooling and processes for packaging have improved. I have had similar experience with Java, C# and Emacs Lisp bindings for GNU Libidn as well, where maintaining them centralized slow down the pace of updates. Andreas Metzler pointed to a similar conclusion reached by Russ Allbery.

There are many ways to separate a project into two projects; just copying the files into a new git repository would have been the simplest and was my original plan. However Ludo’ mentioned git-filter-branch in an email, and the idea of keeping all git history for some of the relevant files seemed worth pursuing to me. I quickly found git-filter-repo which appears to be the recommend approach, and experimenting with it I found a way to filter out the GnuTLS repo into a small git repository that Guile-GnuTLS could be based on. The commands I used were the following, if you want to reproduce things.

$ git clone https://gitlab.com/gnutls/gnutls.git guile-gnutls
$ cd guile-gnutls/
$ git checkout f5dcbdb46df52458e3756193c2a23bf558a3ecfd
$ git-filter-repo --path guile/ --path m4/guile.m4 --path doc/gnutls-guile.texi --path doc/extract-guile-c-doc.scm --path doc/cha-copying.texi --path doc/fdl-1.3.texi

I debated with myself back and forth whether to include some files that would be named the same in the new repository but would share little to no similar lines, for example configure.ac, Makefile.am not to mention README and NEWS. Initially I thought it would be nice to preserve the history for all lines that went into the new project, but this is a subjective judgement call. What brought me over to a more minimal approach was that the contributor history and attribution would be quite strange for the new repository: Should Guile-GnuTLS attribute the work of the thousands of commits to configure.ac which had nothing to do with Guile? Should the people who wrote that be mentioned as contributor of Guile-GnuTLS? I think not.

The next step was to get a reasonable GitLab CI/CD pipeline up, to make sure the project builds on some free GNU/Linux distributions like Trisquel and PureOS as well as the usual non-free distributions like Debian and Fedora to have coverage of dpkg and rpm based distributions. I included builds on Alpine and ArchLinux as well, because they tend to trigger other portability issues. I wish there were GNU Guix docker images available for easy testing on that platform as well. The GitLab CI/CD rules for a project like this are fairly simple.

To get things out of the door, I tagged the result as v3.7.9 and published a GitLab release page for Guile-GnuTLS that includes OpenPGP-signed source tarballs manually uploaded built on my laptop. The URLs for these tarballs are not very pleasant to work with, and discovering new releases automatically appears unreliable, but I don’t know of a better approach.

To finish this project, I have proposed a GnuTLS merge request to remove all Guile-related parts from the GnuTLS core.

Doing some GnuTLS-related work again felt nice, it was quite some time ago so thank you for giving me this opportunity. Thoughts or comments? Happy hacking!

Privilege separation of GSS-API credentials for Apache

Posted on by

To protect web resources with Kerberos you may use Apache HTTPD with mod_auth_gssapi — however, all web scripts (e.g., PHP) run under Apache will have access to the Kerberos long-term symmetric secret credential (keytab). If someone can get it, they can impersonate your server, which is bad.

The gssproxy project makes it possible to introduce privilege separation to reduce the attack surface. There is a tutorial for RPM-based distributions (Fedora, RHEL, AlmaLinux, etc), but I wanted to get this to work on a DPKG-based distribution (Debian, Ubuntu, Trisquel, PureOS, etc) and found it worthwhile to document the process. I’m using Ubuntu 22.04 below, but have tested it on Debian 11 as well. I have adopted the gssproxy package in Debian, and testing this setup is part of the scripted autopkgtest/debci regression testing.

First install the required packages:

root@foo:~# apt-get update
root@foo:~# apt-get install -y apache2 libapache2-mod-auth-gssapi gssproxy curl

This should give you a working and running web server. Verify it is operational under the proper hostname, I’ll use foo.sjd.se in this writeup.

root@foo:~# curl --head http://foo.sjd.se/
HTTP/1.1 200 OK
…

The next step is to create a keytab containing the Kerberos V5 secrets for your host, the exact steps depends on your environment (usually kadmin ktadd or ipa-getkeytab), but use the string “HTTP/foo.sjd.se” and then confirm using something like the following.

root@foo:~# ls -la /etc/gssproxy/httpd.keytab
-rw------- 1 root root 176 Sep 18 06:44 /etc/gssproxy/httpd.keytab
root@foo:~# klist -k /etc/gssproxy/httpd.keytab -e
Keytab name: FILE:/etc/gssproxy/httpd.keytab
KVNO Principal
---- --------------------------------------------------------------------------
   2 HTTP/foo.sjd.se@GSSPROXY.EXAMPLE.ORG (aes256-cts-hmac-sha1-96) 
   2 HTTP/foo.sjd.se@GSSPROXY.EXAMPLE.ORG (aes128-cts-hmac-sha1-96) 
root@foo:~#

The file should be owned by root and not be in the default /etc/krb5.keytab location, so Apache’s libapache2-mod-auth-gssapi will have to use gssproxy to use it.

Then configure gssproxy to find the credential and use it with Apache.

root@foo:~# cat<<EOF > /etc/gssproxy/80-httpd.conf
[service/HTTP]
mechs = krb5
cred_store = keytab:/etc/gssproxy/httpd.keytab
cred_store = ccache:/var/lib/gssproxy/clients/krb5cc_%U
euid = www-data
process = /usr/sbin/apache2
EOF

For debugging, it may be useful to enable more gssproxy logging:

root@foo:~# cat<<EOF > /etc/gssproxy/gssproxy.conf
[gssproxy]
debug_level = 1
EOF
root@foo:~#

Restart gssproxy so it finds the new configuration, and monitor syslog as follows:

root@foo:~# tail -F /var/log/syslog &
root@foo:~# systemctl restart gssproxy

You should see something like this in the log file:

Sep 18 07:03:15 foo gssproxy[4076]: [2022/09/18 05:03:15]: Exiting after receiving a signal
Sep 18 07:03:15 foo systemd[1]: Stopping GSSAPI Proxy Daemon…
Sep 18 07:03:15 foo systemd[1]: gssproxy.service: Deactivated successfully.
Sep 18 07:03:15 foo systemd[1]: Stopped GSSAPI Proxy Daemon.
Sep 18 07:03:15 foo gssproxy[4092]: [2022/09/18 05:03:15]: Debug Enabled (level: 1)
Sep 18 07:03:15 foo systemd[1]: Starting GSSAPI Proxy Daemon…
Sep 18 07:03:15 foo gssproxy[4093]: [2022/09/18 05:03:15]: Kernel doesn't support GSS-Proxy (can't open /proc/net/rpc/use-gss-proxy: 2 (No such file or directory))
Sep 18 07:03:15 foo gssproxy[4093]: [2022/09/18 05:03:15]: Problem with kernel communication! NFS server will not work
Sep 18 07:03:15 foo systemd[1]: Started GSSAPI Proxy Daemon.
Sep 18 07:03:15 foo gssproxy[4093]: [2022/09/18 05:03:15]: Initialization complete.

The NFS-related errors is due to a default gssproxy configuration file, it is harmless and if you don’t use NFS with GSS-API you can silence it like this:

root@foo:~# rm /etc/gssproxy/24-nfs-server.conf
root@foo:~# systemctl try-reload-or-restart gssproxy

The log should now indicate that it loaded the keytab:

Sep 18 07:18:59 foo systemd[1]: Reloading GSSAPI Proxy Daemon…
Sep 18 07:18:59 foo gssproxy[4182]: [2022/09/18 05:18:59]: Received SIGHUP; re-reading config.
Sep 18 07:18:59 foo gssproxy[4182]: [2022/09/18 05:18:59]: Service: HTTP, Keytab: /etc/gssproxy/httpd.keytab, Enctype: 18
Sep 18 07:18:59 foo gssproxy[4182]: [2022/09/18 05:18:59]: New config loaded successfully.
Sep 18 07:18:59 foo systemd[1]: Reloaded GSSAPI Proxy Daemon.

To instruct Apache — or actually, the MIT Kerberos V5 GSS-API library used by mod_auth_gssap loaded by Apache — to use gssproxy instead of using /etc/krb5.keytab as usual, Apache needs to be started in an environment that has GSS_USE_PROXY=1 set. The background is covered by the gssproxy-mech(8) man page and explained by the gssproxy README.

When systemd is used the following can be used to set the environment variable, note the final command to reload systemd.

root@foo:~# mkdir -p /etc/systemd/system/apache2.service.d
root@foo:~# cat<<EOF > /etc/systemd/system/apache2.service.d/gssproxy.conf
[Service]
Environment=GSS_USE_PROXY=1
EOF
root@foo:~# systemctl daemon-reload

The next step is to configure a GSS-API protected Apache resource:

root@foo:~# cat<<EOF > /etc/apache2/conf-available/private.conf
<Location /private>
  AuthType GSSAPI
  AuthName "GSSAPI Login"
  Require valid-user
</Location>

Enable the configuration and restart Apache — the suggested use of reload is not sufficient, because then it won’t be restarted with the newly introduced GSS_USE_PROXY variable. This just applies to the first time, after the first restart you may use reload again.

root@foo:~# a2enconf private
Enabling conf private.
To activate the new configuration, you need to run:
systemctl reload apache2
root@foo:~# systemctl restart apache2

When you have debug messages enabled, the log may look like this:

Sep 18 07:32:23 foo systemd[1]: Stopping The Apache HTTP Server…
Sep 18 07:32:23 foo gssproxy[4182]: [2022/09/18 05:32:23]: Client [2022/09/18 05:32:23]: (/usr/sbin/apache2) [2022/09/18 05:32:23]: connected (fd = 10)[2022/09/18 05:32:23]: (pid = 4651) (uid = 0) (gid = 0)[2022/09/18 05:32:23]:
Sep 18 07:32:23 foo gssproxy[4182]: message repeated 4 times: [ [2022/09/18 05:32:23]: Client [2022/09/18 05:32:23]: (/usr/sbin/apache2) [2022/09/18 05:32:23]: connected (fd = 10)[2022/09/18 05:32:23]: (pid = 4651) (uid = 0) (gid = 0)[2022/09/18 05:32:23]:]
Sep 18 07:32:23 foo systemd[1]: apache2.service: Deactivated successfully.
Sep 18 07:32:23 foo systemd[1]: Stopped The Apache HTTP Server.
Sep 18 07:32:23 foo systemd[1]: Starting The Apache HTTP Server…
Sep 18 07:32:23 foo gssproxy[4182]: [2022/09/18 05:32:23]: Client [2022/09/18 05:32:23]: (/usr/sbin/apache2) [2022/09/18 05:32:23]: connected (fd = 10)[2022/09/18 05:32:23]: (pid = 4657) (uid = 0) (gid = 0)[2022/09/18 05:32:23]:
root@foo:~# Sep 18 07:32:23 foo gssproxy[4182]: message repeated 8 times: [ [2022/09/18 05:32:23]: Client [2022/09/18 05:32:23]: (/usr/sbin/apache2) [2022/09/18 05:32:23]: connected (fd = 10)[2022/09/18 05:32:23]: (pid = 4657) (uid = 0) (gid = 0)[2022/09/18 05:32:23]:]
Sep 18 07:32:23 foo systemd[1]: Started The Apache HTTP Server.

Finally, set up a dummy test page on the server:

root@foo:~# echo OK > /var/www/html/private

To verify that the server is working properly you may acquire tickets locally and then use curl to retrieve the GSS-API protected resource. The "--negotiate" enables SPNEGO and "--user :" asks curl to use username from the environment.

root@foo:~# klist
Ticket cache: FILE:/tmp/krb5cc_0
Default principal: jas@GSSPROXY.EXAMPLE.ORG

Valid starting Expires Service principal
09/18/22 07:40:37 09/19/22 07:40:37 krbtgt/GSSPROXY.EXAMPLE.ORG@GSSPROXY.EXAMPLE.ORG
root@foo:~# curl --negotiate --user : http://foo.sjd.se/private
OK
root@foo:~#

The log should contain something like this:

Sep 18 07:56:00 foo gssproxy[4872]: [2022/09/18 05:56:00]: Client [2022/09/18 05:56:00]: (/usr/sbin/apache2) [2022/09/18 05:56:00]: connected (fd = 10)[2022/09/18 05:56:00]: (pid = 5042) (uid = 33) (gid = 33)[2022/09/18 05:56:00]:
Sep 18 07:56:00 foo gssproxy[4872]: [CID 10][2022/09/18 05:56:00]: gp_rpc_execute: executing 6 (GSSX_ACQUIRE_CRED) for service "HTTP", euid: 33,socket: (null)
Sep 18 07:56:00 foo gssproxy[4872]: [CID 10][2022/09/18 05:56:00]: gp_rpc_execute: executing 6 (GSSX_ACQUIRE_CRED) for service "HTTP", euid: 33,socket: (null)
Sep 18 07:56:00 foo gssproxy[4872]: [CID 10][2022/09/18 05:56:00]: gp_rpc_execute: executing 1 (GSSX_INDICATE_MECHS) for service "HTTP", euid: 33,socket: (null)
Sep 18 07:56:00 foo gssproxy[4872]: [CID 10][2022/09/18 05:56:00]: gp_rpc_execute: executing 6 (GSSX_ACQUIRE_CRED) for service "HTTP", euid: 33,socket: (null)
Sep 18 07:56:00 foo gssproxy[4872]: [CID 10][2022/09/18 05:56:00]: gp_rpc_execute: executing 9 (GSSX_ACCEPT_SEC_CONTEXT) for service "HTTP", euid: 33,socket: (null)

The Apache log will look like this, notice the authenticated username shown.

127.0.0.1 - jas@GSSPROXY.EXAMPLE.ORG [18/Sep/2022:07:56:00 +0200] "GET /private HTTP/1.1" 200 481 "-" "curl/7.81.0"

Congratulations, and happy hacking!

Static network config with Debian Cloud images

Posted on by

I self-host some services on virtual machines (VMs), and I’m currently using Debian 11.x as the host machine relying on the libvirt infrastructure to manage QEMU/KVM machines. While everything has worked fine for years (including on Debian 10.x), there has always been one issue causing a one-minute delay every time I install a new VM: the default images run a DHCP client that never succeeds in my environment. I never found out a way to disable DHCP in the image, and none of the documented ways through cloud-init that I have tried worked. A couple of days ago, after reading the AlmaLinux wiki I found a solution that works with Debian.

The following commands creates a Debian VM with static network configuration without the annoying one-minute DHCP delay. The three essential cloud-init keywords are the NoCloud meta-data parameters dsmode:local, static network-interfaces setting combined with the user-data bootcmd keyword. I’m using a Raptor CS Talos II ppc64el machine, so replace the image link with a genericcloud amd64 image if you are using x86.

wget https://cloud.debian.org/images/cloud/bullseye/latest/debian-11-generic-ppc64el.qcow2
cp debian-11-generic-ppc64el.qcow2 foo.qcow2

cat>meta-data
dsmode: local
network-interfaces: |
 iface enp0s1 inet static
 address 192.168.98.14/24
 gateway 192.168.98.12
^D

cat>user-data
#cloud-config
fqdn: foo.mydomain
manage_etc_hosts: true
disable_root: false
ssh_pwauth: false
ssh_authorized_keys:
- ssh-ed25519 AAAA...
timezone: Europe/Stockholm
bootcmd:
- rm -f /run/network/interfaces.d/enp0s1
- ifup enp0s1
^D

virt-install --name foo --import --os-variant debian10 --disk foo.qcow2 --cloud-init meta-data=meta-data,user-data=user-data

Unfortunately virt-install from Debian 11 does not support the –cloud-init network-config parameter, so if you want to use a version 2 network configuration with cloud-init (to specify IPv6 addresses, for example) you need to replace the final virt-install command with the following.

cat>network_config_static.cfg
version: 2
 ethernets:
  enp0s1:
   dhcp4: false
   addresses: [ 192.168.98.14/24, fc00::14/7 ]
   gateway4: 192.168.98.12
   gateway6: fc00::12
   nameservers:
    addresses: [ 192.168.98.12, fc00::12 ]
^D

cloud-localds -v -m local --network-config=network_config_static.cfg seed.iso user-data

virt-install --name foo --import --os-variant debian10 --disk foo.qcow2 --disk seed.iso,readonly=on --noreboot

virsh start foo
virsh detach-disk foo vdb --config
virsh console foo

There are still some warnings like the following, but it does not seem to cause any problem:

[FAILED] Failed to start Initial cloud-init job (pre-networking).

Finally, if you do not want the cloud-init tools installed in your VMs, I found the following set of additional user-data commands helpful. Cloud-init will not be enabled on first boot and a cron job will be added that purges some unwanted packages.

runcmd:
- touch /etc/cloud/cloud-init.disabled
- apt-get update && apt-get dist-upgrade -uy && apt-get autoremove --yes --purge && printf '#!/bin/sh\n{ rm /etc/cloud/cloud-init.disabled /etc/cloud/cloud.cfg.d/01_debian_cloud.cfg && apt-get purge --yes cloud-init cloud-guest-utils cloud-initramfs-growroot genisoimage isc-dhcp-client && apt-get autoremove --yes --purge && rm -f /etc/cron.hourly/cloud-cleanup && shutdown --reboot +1; } 2>&1 | logger -t cloud-cleanup\n' > /etc/cron.hourly/cloud-cleanup && chmod +x /etc/cron.hourly/cloud-cleanup && reboot &

The production script I’m using is a bit more complicated, but can be downloaded as vello-vm. Happy hacking!

Towards pluggable GSS-API modules

Posted on by

GSS-API is a standardized framework that is used by applications to, primarily, support Kerberos V5 authentication. GSS-API is standardized by IETF and supported by protocols like SSH, SMTP, IMAP and HTTP, and implemented by software projects such as OpenSSH, Exim, Dovecot and Apache httpd (via mod_auth_gssapi). The implementations of Kerberos V5 and GSS-API that are packaged for common GNU/Linux distributions, such as Debian, include MIT Kerberos, Heimdal and (less popular) GNU Shishi/GSS.

When an application or library is packaged for a GNU/Linux distribution, a choice is made which GSS-API library to link with. I believe this leads to two problematic consequences: 1) it is difficult for end-users to chose between Kerberos implementation, and 2) dependency bloat for non-Kerberos users. Let’s discuss these separately.

  1. No system admin or end-user choice over the GSS-API/Kerberos implementation used

    There are differences in the bug/feature set of MIT Kerberos and that of Heimdal’s, and definitely that of GNU Shishi. This can lead to a situation where an application (say, Curl) is linked to MIT Kerberos, and someone discovers a Kerberos related problem that would have been working if Heimdal was used, or vice versa. Sometimes it is possible to locally rebuild a package using another set of dependencies. However doing so has a high maintenance cost to track security fixes in future releases. It is an unsatisfying solution for the distribution to flip flop between which library to link to, depending on which users complain the most. To resolve this, a package could be built in two variants: one for MIT Kerberos and one for Heimdal. Both can be shipped. This can help solve the problem, but the question of which variant to install by default leads to similar concerns, and will also eventually leads to dependency conflicts. Consider an application linked to libraries (possible in several steps) where one library only supports MIT Kerberos and one library only supports Heimdal.

    The fact remains that there will continue to be multiple Kerberos implementations. Distributions will continue to support them, and will be faced with the dilemma of which one to link to by default. Distributions and the people who package software will have little guidance on which implementation to chose from their upstream, since most upstream support both implementations. The result is that system administrators and end-users are not given a simple way to have flexibility about which implementation to use.
  2. Dependency bloat for non-Kerberos use-cases.

    Compared to the number of users of GNU/Linux systems out there, the number of Kerberos users on GNU/Linux systems is smaller. Here distributions face another dilemma. Should they enable GSS-API for all applications, to satisfy the Kerberos community, or should they be conservative with adding dependencies to reduce attacker surface for the non-Kerberos users? This is a dilemma with no clear answer, and one approach has been to ship two versions of a package: one with Kerberos support and one without. Another option here is for upstream to support loadable modules, for example Dovecot implement this and Debian ship with a separate ‘dovecot-gssapi’ package that extend the core Dovecot seamlessly. Few except some larger projects appear to be willing to carry that maintenance cost upstream, so most only support build-time linking of the GSS-API library.

    There are a number of real-world situations to consider, but perhaps the easiest one to understand for most GNU/Linux users is OpenSSH. The SSH protocol supports Kerberos via GSS-API, and OpenSSH implement this feature, and most GNU/Linux distributions ship a SSH client and SSH server linked to a GSS-API library. Someone made the choice of linking it to a GSS-API library, for the arguable smaller set of people interested in it, and also the choice which library to link to. Rebuilding OpenSSH locally without Kerberos support comes with a high maintenance cost. Many people will not need or use the Kerberos features of the SSH client or SSH server, and having it enabled by default comes with a security cost. Having a vulnerability in OpenSSH is critical for many systems, and therefor its dependencies are a reasonable concern. Wouldn’t it be nice if OpenSSH was built in a way that didn’t force you to install MIT Kerberos or Heimdal? While still making it easy for Kerberos users to use it, of course.

Hopefully I have made the problem statement clear above, and that I managed to convince you that the state of affairs is in need of improving. I learned of the problems from my personal experience with maintaining GNU SASL in Debian, and for many years I ignored this problem.

Let me introduce Libgssglue!

Matryoshka Dolls
Matryoshka Dolls – photo CC-4.0-BY-NC by PngAll

Libgssglue is a library written by Kevin W. Coffman based on historical GSS-API code, the initial release was in 2004 (using the name libgssapi) and the last release was in 2012. Libgssglue provides a minimal GSS-API library and header file, so that any application can link to it instead of directly to MIT Kerberos or Heimdal (or GNU GSS). The administrator or end-user can select during run-time which GSS-API library to use, through a global /etc/gssapi_mech.conf file or even a local GSSAPI_MECH_CONF environment variable. Libgssglue is written in C, has no external dependencies, and is BSD-style licensed. It was developed for the CITI NFSv4 project but libgssglue ended up not being used.

I have added support to build GNU SASL with libgssglue — the changes required were only ./configure.ac-related since GSS-API is a standardized framework. I have written a fairly involved CI/CD check that builds GNU SASL with MIT Kerberos, Heimdal, libgssglue and GNU GSS, sets ups a local Kerberos KDC and verify successful GSS-API and GS2-KRB5 authentications. The ‘gsasl’ command line tool connects to a local example SMTP server, also based on GNU SASL (linked to all variants of GSS-API libraries), and to a system-installed Dovecot IMAP server that use the MIT Kerberos GSS-API library. This is on Debian but I expect it to be easily adaptable to other GNU/Linux distributions. The check triggered some (expected) Shishi/GSS-related missing features, and triggered one problem related to authorization identities that may be a bug in GNU SASL. However, testing shows that it is possible to link GNU SASL with libgssglue and have it be operational with any choice of GSS-API library that is shipped with Debian. See GitLab CI/CD code and its CI/CD output.

This experiment worked so well that I contacted Kevin to learn that he didn’t have any future plans for the project. I have adopted libgssglue and put up a Libgssglue GitLab project page, and pushed out a libgssglue 0.5 release fixing only some minor build-related issues. There are still some missing newly introduced GSS-API interfaces that could be added, but I haven’t been able to find any critical issues with it. Amazing that an untouched 10 year old project works so well!

My current next steps are:

  • Release GNU SASL with support for Libgssglue and encourage its use in documentation.
  • Make GNU SASL link to Libgssglue in Debian, to avoid a hard dependency on MIT Kerberos, but still allowing a default out-of-the-box Kerberos experience with GNU SASL.
  • Maintain libgssglue upstream and implement self-checks, CI/CD testing, new GSS-API interfaces that have been defined, and generally fix bugs and improve the project. Help appreciated!
  • Maintain the libgssglue package in Debian.
  • Look into if there are applications in Debian that link to a GSS-API library that could instead be linked to libgssglue to allow flexibility for the end-user and reduce dependency bloat.

What do you think? Happy Hacking!

OpenPGP smartcard with GNOME on Debian 11 Bullseye

Posted on by

The Debian operating system is what I have been using on my main computer for what is probably around 20 years. I am now in the process of installing the hopefully soon released Debian 11 “bullseye” on my Lenovo X201 laptop. Getting a OpenPGP smartcard to work has almost always required some additional effort, but it has been reliable enough to use exclusively for my daily GnuPG and SSH operations since 2006. In the early days, the issues with smartcards were not related to GNOME, see my smartcard notes for Debian 4 Etch for example. I believe with Debian 5 Lenny, Debian 6 Squeeze, and Debian 7 Stretch things just worked without workarounds, even with GNOME. Those were the golden days! Back in 2015, with Debian 8 Jessie I noticed a regression and came up with a workaround. The problems in GNOME were not fixed, and I wrote about how to work around this for Debian 9 Stretch and the slightly different workaround needed for Debian 10 Buster. What will Bullseye be like?

The first impression of working with GnuPG and a smartcard is still the same. After inserting the GNUK that holds my private keys into my laptop, nothing happens by default and attempting to access the smartcard results in the following.

jas@latte:~$ gpg --card-status
gpg: error getting version from 'scdaemon': No SmartCard daemon
gpg: OpenPGP card not available: No SmartCard daemon
jas@latte:~$

The solution is to install the scdaemon package. My opinion is that either something should offer to install it when the device is inserted (wasn’t there a framework for discovering hardware and installing the right packages?) or this package should always be installed for a desktop system. Anyway, the following solves the problem.

jas@latte:~$ sudo apt install scdaemon
...
jas@latte:~$ gpg --card-status
 Reader ………..: 234B:0000:FSIJ-1.2.14-67252015:0
 Application ID …: D276000124010200FFFE672520150000
...
 URL of public key : https://josefsson.org/key-20190320.txt
...

Before the private key in the smartcard can be used, the public key must be imported into GnuPG. I now believe the best way to do this (see earlier posts for alternatives) is to configure the smartcard with a public key URL and retrieve it as follows.

jas@latte:~$ gpg --card-edit
 Reader ………..: 234B:0000:FSIJ-1.2.14-67252015:0
...
 gpg/card> fetch
 gpg: requesting key from 'https://josefsson.org/key-20190320.txt'
 gpg: key D73CF638C53C06BE: public key "Simon Josefsson simon@josefsson.org" imported
 gpg: Total number processed: 1
 gpg:               imported: 1
 gpg/card> quit
jas@latte:~$ gpg -K
 /home/jas/.gnupg/pubring.kbx
 sec#  ed25519 2019-03-20 [SC] [expires: 2021-08-21]
       B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE
 uid           [ unknown] Simon Josefsson simon@josefsson.org
 ssb>  ed25519 2019-03-20 [A] [expires: 2021-08-21]
 ssb>  ed25519 2019-03-20 [S] [expires: 2021-08-21]
 ssb>  cv25519 2019-03-20 [E] [expires: 2021-08-21]
jas@latte:~$

The next step is to mark your own key as ultimately trusted, use the fingerprint shown above together with gpg --import-ownertrust. Warning! This is not the general way to remove the warning about untrusted keys, this method should only be used for your own keys.

jas@latte:~$ echo "B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE:6:" | gpg --import-ownertrust
gpg: inserting ownertrust of 6
jas@latte:~$ gpg -K
gpg: checking the trustdb
gpg: marginals needed: 3  completes needed: 1  trust model: pgp
gpg: depth: 0  valid:   1  signed:   0  trust: 0-, 0q, 0n, 0m, 0f, 1u
gpg: next trustdb check due at 2021-08-21
 /home/jas/.gnupg/pubring.kbx
sec#  ed25519 2019-03-20 [SC] [expires: 2021-08-21]
       B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE
uid           [ultimate] Simon Josefsson simon@josefsson.org
ssb>  cv25519 2019-03-20 [E] [expires: 2021-08-21]
ssb>  ed25519 2019-03-20 [A] [expires: 2021-08-21]
ssb>  ed25519 2019-03-20 [S] [expires: 2021-08-21]
jas@latte:~$

Now GnuPG is able to both sign, encrypt, and decrypt data:

jas@latte:~$ echo foo|gpg -a --sign|gpg --verify
 gpg: Signature made Sat May  1 16:02:49 2021 CEST
 gpg:                using EDDSA key A3CC9C870B9D310ABAD4CF2F51722B08FE4745A2
 gpg: Good signature from "Simon Josefsson simon@josefsson.org" [ultimate]
 jas@latte:~$ echo foo|gpg -a --encrypt -r simon@josefsson.org|gpg --decrypt
 gpg: encrypted with 256-bit ECDH key, ID 02923D7EE76EBD60, created 2019-03-20
       "Simon Josefsson simon@josefsson.org"
 foo
jas@latte:~$

To make SSH work with the smartcard, the following is the GNOME-related workaround that is still required. The problem is that the GNOME keyring enables its own incomplete SSH-agent implementation. It is lacking the smartcard support that the GnuPG agent can provide, and even set the SSH_AUTH_SOCK environment variable if the enable-ssh-support parameter is provided.

jas@latte:~$ ssh-add -L
 The agent has no identities.
jas@latte:~$ echo $SSH_AUTH_SOCK 
 /run/user/1000/keyring/ssh
jas@latte:~$ mkdir -p ~/.config/autostart
jas@latte:~$ cp /etc/xdg/autostart/gnome-keyring-ssh.desktop ~/.config/autostart/
jas@latte:~$ echo 'Hidden=true' >> .config/autostart/gnome-keyring-ssh.desktop 
jas@latte:~$ echo enable-ssh-support >> ~/.gnupg/gpg-agent.conf

For some reason, it does not seem sufficient to log out of GNOME and then login again. Most likely some daemon is still running, that has to be restarted. At this point, I reboot my laptop and then log into GNOME again. Finally it looks correct:

jas@latte:~$ echo $SSH_AUTH_SOCK 
 /run/user/1000/gnupg/S.gpg-agent.ssh
jas@latte:~$ ssh-add -L
 ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAILzCFcHHrKzVSPDDarZPYqn89H5TPaxwcORgRg+4DagE cardno:FFFE67252015
jas@latte:~$

Please discuss in small groups the following topics:

  • How should the scdaemon package be installed more automatically?
  • Should there a simple command to retrieve the public key for a smartcard and set it as ultimately trusted? The two step --card-edit and --import-ownertrust steps is a bad user interface and is not intuitive in my opinion.
  • Why is GNOME keyring used for SSH keys instead of ssh-agent/gpg-agent?
  • Should gpg-agent have enable-ssh-support on by default?

After these years, I would probably feel a bit of sadness if the problems were fixed, since then I wouldn’t be able to rant about this problem and celebrate installing Debian 12 Bookworm the same way I have done for the some past releases.

Thanks for reading and happy hacking!