This guide will show you how to sign, encrypt, and decrypt content where GPG is in a Coder workspace while the private key is on your local machine.

Step 1: Configure your local machine

We assume that you're already capable of using and signing GPG on your local machine.

The examples in this guide were created using macOS 11 (Big Sur); Windows and Linux users may need to modify the provided instructions.

First, make sure that you've:

• Installed GnuPG (GPG) using Homebrew or gpg-suite
• Verified that pinentry is installed (if not, install pinentry)
• Created or imported both your public and private GPG keys

You can verify your GnuPG installation and version number as follows:

gpg --version
gpg (GnuPG) 2.3.1

Starting GnuPG

When running any gpg command, your system knows to start gpg-agent, which creates the sockets needed and performs the cryptographic activity. However, if you connect to a workspace via SSH using the -R flag to remote forward the sockets, your local gpg-agent won't start automatically since this process doesn't invoke the gpg binary.

To address this issue, add the gpg-agent to your local .profile, .bashrc, .zshrc, or configuration script that runs for each terminal session:

gpgconf --launch gpg-agent

Alternatively, you can run gpg-agent --daemon to prepare your local system.

If you don't perform either of the steps above, there won't be sockets for mounting and the remote gpg command won't work (instead, you'll end up starting an agent in the remote system that has no keys).

Step 2: Configure Coder

The following steps must be performed by a Coder user assigned the site manager role.

To use GPG agent forwarding, ensure that you've enabled:

• SSH access to workspaces; you must use OpenSSH (the basic libssh server doesn't support forwarding)
• Container-based virtual machines (CVMs); CVMs are required to run systemd, which is required for OpenSSH to start

Step 3: Configure a Coder image to support GPG forwarding

Update the image on which your workspace is based to include the following dependencies for GPG forwarding:

• openssh-server and gnupg2 installed
• StreamLocalBindUnlink yes set in the /etc/ssh/sshd_config file
• Socket masking
• OpenSSH enabled (so that Coder doesn't inject its own ssh daemon)

Your updated Dockerfile would look something like:

FROM ubuntu:20:04
RUN apt-get update && \
    DEBIAN_FRONTEND="noninteractive" apt-get install --yes \
    openssh-server \
    gnupg2 \
    systemd \
    systemd-sysv

RUN echo  "StreamLocalBindUnlink yes" >> /etc/ssh/sshd_config && \
    systemctl --global mask gpg-agent.service \
    gpg-agent.socket gpg-agent-ssh.socket \
    gpg-agent-extra.socket gpg-agent-browser.socket && \
    systemctl enable ssh

Alternatively, you can create a new image from scratch. If so, we recommend starting with Coder's Enterprise Base image, which helps establish dependencies and conventions that improves the Coder user experience.

If you use the Enterprise Base image as your starting point:

1. run apt-get install gnupg2 openssh-server

2. Add the following to the Dockerfile:

   RUN echo  "StreamLocalBindUnlink yes" >> /etc/ssh/sshd_config && \
       systemctl --global mask gpg-agent.service \
       gpg-agent.socket gpg-agent-ssh.socket \
       gpg-agent-extra.socket gpg-agent-browser.socket && \
       systemctl enable ssh
   

Step 4: Create/update a workspace using the image

Once you've created your image, you can import it for use. When creating a workspace using that image, be sure to create a CVM-enabled workspace.

Step 5: Define the workspace-startup configurations using dotfiles

The configuration detailed in this section must be be run after you've created and started your workspace (the configurations must be run within the context of your user). We recommend defining your configuration using Coder personalization scripts (otherwise known as dotfiles).

To use your local private key on the remote Coder workspace, you must provide the workspace a reference to the public key and the key must be trusted. You must also account for the fact that not all images will include GPG. To do both, add the following to an install.sh script, then add the file to your dotfiles repo:

if hash gpg 2>/dev/null; then
  echo "gpg found, configuring public key"
  gpg --import ~/dotfiles/.gnupg/mterhar_coder.com-publickey.asc
  echo "16AD...B84AC:6:" | gpg --import-ownertrust
  git config --global user.signingkey F371232FA31B84AC
  echo "pinentry-mode loopback" > ~/.gnupg/gpg.conf
  echo "export GPG_TTY=\$(tty)" > ~/.profile
  echo "to enable commit signing, run"
  echo "git config --global commit.gpgsign true"
else
  echo "gpg not found, no git signing"
fi

Notes regarding the sample script:

• Adding the public key export directly to the dotfiles repository (as shown in the example) allows it to be imported.
• The gpg --import-ownertrust command gets the fingerprint of the key that was just imported with a trust level of 6 (this indicates a trust level of ultimate).
• The "pinentry-mode loopback" > ~/.gnupg/gpg.conf allows the remote system to trigger pinentry inline so that you can type your passphrase into the same terminal where you're running the GPG command to unlock the mounted socket.
• Setting GPG_TTY allows pinentry time to send the request for a passphrase to the correct place. The use of a single > prevents that line from being added to .profile repeatedly, though anything you have in the file will be erased.

Step 6: Connect to Coder

On your local machine, ensure that gpg-agent is running and that it works when you attempt to perform a GPG action (e.g., echo "test" | gpg --clearsign). Note that you'll be prompted to provide your pin; as such, the socket will be open for a bit unless you kill and restart the GPG agent.

To launch gpg-agent and connect to Coder:

gpgconf --launch gpg-agent
coder config-ssh
ssh -R /run/user/1000/gnupg/S.gpg-agent:/Users/mterhar/.gnupg/S.gpg-agent coder.<workspace name>

At this point, there is a connection from your local filesystem socket to the remote filesystem socket, so you can begin running GPG actions:

$ echo "test " | gpg --clearsign -v
gpg: using character set 'utf-8'
gpg: using pgp trust model
gpg: key F371232FA31B84AC: accepted as trusted key
gpg: writing to stdout
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

test
gpg: EDDSA/SHA256 signature from: "F371232FA31B84AC Mike Terhar <[email protected]>"
-----BEGIN PGP SIGNATURE-----

iHUEARYIAB0WIQQWraRO2qW8c4RXhlTzcSMvoxuErAUCYPm2fwAKCRDzcSMvoxuE
rHYNAQCrGPbF9Z89dDjemFMtgt0dfsPSUcAlgVj1PKGsg/K8lgEAj8MeTXi1RQhv
dqbC8blPKTAzupH7OeQpe6EbweZHjAI=
=tgC/
-----END PGP SIGNATURE-----

If you decide to run a web terminal or use the terminal within code-server, you'll be prompted for to enter your pin and to use the SSH socket (this is true for terminals that are running from different devices as well).

Example: GPG forwarding action

The following is an example of what a GPG forwarding action looks like:

% gpgconf --launch gpg-agent
% ssh -R /run/user/1000/gnupg/S.gpg-agent:/Users/mterhar/.gnupg/S.gpg-agent coder.gpg
Welcome to Ubuntu 20.04.2 LTS (GNU/Linux 5.4.0-1039-gke x86_64)

 * Documentation:  https://help.ubuntu.com
 * Management:     https://landscape.canonical.com
 * Support:        https://ubuntu.com/advantage

This system has been minimized by removing packages and content that are
not required on a system that users do not log into.

To restore this content, you can run the 'unminimize' command.
Last login: Thu Jul 22 18:17:57 2021 from 127.0.0.1

$ echo "test " | gpg --clearsign -v
gpg: using character set 'utf-8'
gpg: using pgp trust model
gpg: key F371232FA31B84AC: accepted as trusted key
gpg: writing to stdout
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

test
gpg: EDDSA/SHA256 signature from: "F371232FA31B84AC Mike Terhar <[email protected]>"
-----BEGIN PGP SIGNATURE-----

iHUEARYIAB0WIQQWraRO2qW8c4RXhlTzcSMvoxuErAUCYPm2fwAKCRDzcSMvoxuE
rHYNAQCrGPbF9Z89dDjemFMtgt0dfsPSUcAlgVj1PKGsg/K8lgEAj8MeTXi1RQhv
dqbC8blPKTAzupH7OeQpe6EbweZHjAI=
=tgC/
-----END PGP SIGNATURE-----

To sign Git commits via the command line:

$ git commit -m "trigger signature"
[gpg-test 2ece8ea] trigger signature
 1 file changed, 2 insertions(+)
$ git verify-commit 2ece8ea
gpg: Signature made Thu Jul 22 19:15:50 2021 UTC
gpg:                using EDDSA key 16ADA44EDAA5BC7384578654F371232FA31B84AC
gpg: Good signature from "Mike Terhar <[email protected]>" [ultimate]

Now, when you push commits to GitHub/GitLab, you'll see that the commits are flagged as verified.

Using a Yubikey or other smart card

The Yubikey configurations required to make GPG work with the local machine are all that is necessary to use it as a smart card.

Once you've configured Yibikey, you can follow the steps detailed in this article to set up GPG forwarding; the only difference is that you should provide pinentry with your Yubikey PIN, not the private key passphrase.

As soon as the cryptographic action is complete, be sure remove the Yubikey from the USB port to prevent any additional cryptographic actions from occurring through the GPG forwarding socket.

Limitations for code-server users

The Git functionality in code-server will sign the commit and obey the .gitconfig file. However, it lacks the ability to ask for a GPG pin, so the forwarding process only works if the socket is already open due to some other activity. For example, the following Git CLI command would typically prompt you to unlock the GPG key:

git verify-commit <commit>

However, if the socket isn't already open, you'd get an error saying Git: gpg failed to sign the data, even if the configuration setting is enabled:

"git.enableCommitSigning": true

Security considerations

Any time you use a private key, you expose it to the systems that are granted access to the key.

Furthermore, actions such as typing the passphrase or using gpg-preset-passphrase to keep the socket open each have different risk profiles associated (e.g., the risk of someone looking over your shoulder and the risk of someone accessing the system with open socket from another terminal).

The following are steps you can take to minimize your risk:

1. Setting default-cache-ttl 30, which will prompt you for your PIN more frequently. While the signing activity only takes a short amount of time to complete, the GPG socket remains open longer.

2. Connect to the local .extra socket rather than the primary socket, which helps limit key exposure (if you do this, modify examples in this article to use the appropriate socket).

3. Create a separate sub-key for Coder to use to prevent the primary key from being compromised if a security incident occurs. You'll need to add the sub-keys to your Git provider, and if there's a security incident, the old commits signed using the affected keys may be considered unverified.

4. As of Coder v1.22.x, running coder config-ssh enables the ControlMaster mechanism, which caches connections even you exit the interactive shell. This means that GPG actions on the remote system can occur even if there's no apparent connection. To disable ControlMaster on your GPG-forwarded SSH connection, add the following options to your command: -o ControlMaster=no -o ControlPath=none.

Troubleshooting

The following sections explain how you can troubleshoot errors you may see when using up GPG forwarding.

Unable to connect to the default agent port

connect to /Users/mterhar/.gnupg/S.gpg-agent port -2 failed: No such file or directory
gpg: no running gpg-agent - starting '/usr/bin/gpg-agent'

If you see this error, the socket wasn't present on the local machine when you executed your ssh command. This is caused by a lack of -R or ForwardRemote in the ssh configuration, so update your configuration accordingly.

No secret key

gpg: key F371232FA31B84AC: accepted as trusted key
gpg: no default secret key: No secret key
gpg: [stdin]: clear-sign failed: No secret key

This error can happen if there's a gpg agent running in the remote workspace that is intercepting the GPG commands before they get to the remote socket.

You can fix this by:

1. Running gpgconf --kill gpg-agent
2. Using ps ax | grep gpg-agent to find and kill all of the pids.

Then, reconnect your ssh session to re-establish the socket forwarding.

Inappropriate ioctl for the device

$ echo "test " | gpg --clearsign -vvv
gpg: using character set 'utf-8'
gpg: using pgp trust model
gpg: key F371232FA31B84AC: accepted as trusted key
gpg: writing to stdout
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA256

test
gpg: pinentry launched (1744 curses 1.1.1 - xterm-256color - - 501/20 0)
gpg: signing failed: Inappropriate ioctl for device
gpg: [stdin]: clear-sign failed: Inappropriate ioctl for device

If gpg: pinentry launched (1744 curses 1.1.1 - xterm-256color - - 501/20 0) does not include the /dev/pts/1 after the version number, you may need to add the GPG_TTY environment variable to a process that runs before trying to use gpg.

If GPG_TTY is set to the same output as tty, be sure you have a .gnupg/gpg.conf file that contains pinentry-mode loopback.

SSH error with remote port forwarding

If you receive this error when connecting via SSH:

Warning: remote port forwarding failed for listen path
/run/user/1000/gnupg/S.gpg-agent

The likely cause is that openssh isn't running. This could be a result of:

• The image you're using doesn't include openssh
• The systemctl enable ssh command didn't work
• The workspace doesn't have CVMs enabled.

Unverified commits in GitHub or GitLab

Both GitHub and GitLab display verification statuses beside signed commits. If you see a commit that's unverified, it could be that the signing key hasn't been uploaded to the associated account.

To fix this issue, add the GPG key to your account:

• GitHub: Adding a GPG key
• GitLab: Adding a GPG key

If this doesn't fix the issue, ensure that the email address in the author field matches the email associated with the username and signing key.

The signing still works after disconnecting the session

Coder CLI's coder config-ssh command uses session caching:

Host coder.[workspace name]
   [...]
   ControlMaster auto
   ControlPath ~/.ssh/.connection-%r@%h:%p
   ControlPersist 600

Therefore, the connection persists for some time and the GPG socket forwarding remains open to make opening a new shell fast.

Verbose logging

If you're having issues with GPG forwarding, getting verbose logs is helpful for pinpointing where the issue may be. One way to do so is to add -v to the SSH command you run.

You can also add --verbose to the gpg command. For example, if your sockets aren't where you expected them and you receive the following output, you'll need to get additional information via verbose logs:

$ gpgconf --list-dirs
sysconfdir:/etc/gnupg
bindir:/usr/bin
libexecdir:/usr/lib/gnupg
libdir:/usr/lib/x86_64-linux-gnu/gnupg
datadir:/usr/share/gnupg
localedir:/usr/share/locale
socketdir:/run/user/1000/gnupg
dirmngr-socket:/run/user/1000/gnupg/S.dirmngr
agent-ssh-socket:/run/user/1000/gnupg/S.gpg-agent.ssh
agent-extra-socket:/run/user/1000/gnupg/S.gpg-agent.extra
agent-browser-socket:/run/user/1000/gnupg/S.gpg-agent.browser
agent-socket:/run/user/1000/gnupg/S.gpg-agent
homedir:/home/coder/.gnupg