macOS Nitrokey Pro 2 Guide

This guide shows the setup of a Nitrokey Pro 2 with GnuPG on macOS.

Content

• Prerequisites
• Nitrokey App
• Set up GnuPG
• SSH
• Git (Coming Soon)
• GitHub / GitLab (Coming Soon)
• Thunderbird
• Git-Tower / Transmit

Prerequisites

During the guide you will need to install some additional tools. You will use Homebrew to install all of these. If you don't have Homebrew installed on your system yet, follow the link below.

Homebrew | brew.sh

Nitrokey App

If it is your first Nitrokey, you will need to install the Nitrokey App to change the user as well as the admin PIN. By default, the user PIN has the value 123456, and the admin PIN has the value 12345678.

Please change the PIN's before you continue!

Install Nitrokey App

Nitrokey App Releases

Set up GnuPG

GnuPG implements the OpenPGP standard and can be seen here as a middleware between your applications like Thunderbird or git and your Nitrokey.

Install gnupg2

brew install gnupg2

You can test the installation of GnuPG by running:

gpg --help

If you run gpg for the first time, gpg will create the folder .gnupg in your home directory.

Create OpenPGP keys and move them onto your Nitrokey

The Nitrokey website already provides a very good tutorial about how to create OpenPGP keys and move them onto your Nitrokey. You can find the tutorial here: OpenPGP Key Generation With Backup | nitrokey.com

Install pinentry-mac

Next, you need to install pinentry-mac | github.com. GnuPG already comes with a pinentry-program but this is for terminal use only. Later in this tutorial we want to integrate GnuPG with other applications like Thunderbird. In this case you don't have access to a terminal to enter your user PIN. Therefore you need pinentry-mac. pinentry-mac pops up as an application window where you can enter your PIN.

brew install pinentry-mac

Create gpg.conf

Now you have to change the gpg.conf. The config below was taken from drduh | github.com and is a good point to start with. If you already use your own personal config, please make sure that it contains the options use-agent and no-tty at least. use-agent is required for SSH support | nitrokey.com and no-tty is required by Git-Tower | git-tower.com if you want to use gpg within Git-Tower.

# https://github.com/drduh/config/blob/master/gpg.conf
# https://www.gnupg.org/documentation/manuals/gnupg/GPG-Configuration-Options.html
# https://www.gnupg.org/documentation/manuals/gnupg/GPG-Esoteric-Options.html
# Use AES256, 192, or 128 as cipher
personal-cipher-preferences AES256 AES192 AES
# Use SHA512, 384, or 256 as digest
personal-digest-preferences SHA512 SHA384 SHA256
# Use ZLIB, BZIP2, ZIP, or no compression
personal-compress-preferences ZLIB BZIP2 ZIP Uncompressed
# Default preferences for new keys
default-preference-list SHA512 SHA384 SHA256 AES256 AES192 AES ZLIB BZIP2 ZIP Uncompressed
# SHA512 as digest to sign keys
cert-digest-algo SHA512
# SHA512 as digest for symmetric ops
s2k-digest-algo SHA512
# AES256 as cipher for symmetric ops
s2k-cipher-algo AES256
# UTF-8 support for compatibility
charset utf-8
# Show Unix timestamps
fixed-list-mode
# No comments in signature
no-comments
# No version in signature
no-emit-version
# Long hexidecimal key format
keyid-format 0xlong
# Display UID validity
list-options show-uid-validity
verify-options show-uid-validity
# Display all keys and their fingerprints
with-fingerprint
# Display key origins and updates
#with-key-origin
# Cross-certify subkeys are present and valid
require-cross-certification
# Disable caching of passphrase for symmetrical ops
no-symkey-cache
# Disable putting recipient key IDs into messages
throw-keyids
use-agent
# Make sure that the TTY (terminal) is never used for any output. 
no-tty

Move the config to ~/.gnupg/:

mv gpg.conf ~/.gnupg/

SSH

In this section you will prepare the gpg-agent for ssh support and configure your shell so that it will take the gpg-agent as SSH identity agent instead of the default macOS ssh-agent.

Create gpg-agent.conf

Let's start by creating a gpg-agent config. You can use the config below or create your own one. It is important that your config contains the option enable-ssh-support for ssh support. At the same time you can already set the pinentry-program to /usr/local/bin/pinentry-mac if you want to integrate gpg in Thunderbird or Git-Tower.

default-cache-ttl 600
max-cache-ttl 7200
enable-ssh-support
pinentry-program /usr/local/bin/pinentry-mac

Move the agent config to ~/.gnupg/:

mv gpg-agent.conf ~/.gnupg/

Reload the gpg-agent to apply the changes:

gpgconf --reload gpg-agent

Configure your profile

unset SSH_AGENT_PID
if [ "${gnupg_SSH_AUTH_SOCK_by:-0}" -ne $$ ]; then
	export SSH_AUTH_SOCK="$(gpgconf --list-dirs agent-ssh-socket)"
fi

Create sshcontrol

If you have more than one authentication key but you only want to allow a specific one to be used for ssh, you can put this key into the sshcontrol file. The sshcontrol file contains all gpg authentication keys that are allowed to be used for ssh by the gpg-agent.

First, we need to get the keygrip of your authentication key:

gpg -K --with-keygrip 

Output:

/home/alice/.gnupg/pubring.kbx
-------------------------------
sec>  rsa2048/CB2F38F25B491A54 2019-11-24 [SC]
      Keygrip = D4DF0C35D3E22FA6AC37DA2E54FB03F73616A3CB
      Kartenseriennr. = XXXX XXXXXXXX
uid                [ ultimativ ] Alice <[email protected]>
ssb>  rsa2048/04BB7F8FDEC5E5D9 2019-11-24 [E]
      Keygrip = 21B2EDF018D7CAF0B45644FDB753DD42307C4425
ssb>  rsa2048/BBB6B86627C2D43A 2019-11-24 [A]
      Keygrip = 2E149DA9C5E46E0DECC6A17EFD8B5FB1DF1E1BAB

Add the keygrip of your authentication key [A] to your sshcontrol file:

# List of allowed ssh keys. Only keys present in this file are used
# in the SSH protocol. The ssh-add tool may add new entries to this.

2E149DA9C5E46E0DECC6A17EFD8B5FB1DF1E1BAB

Move the sshcontrol file to ~/.gnupg/:

mv sshcontrol ~/.gnupg/

Reload the gpg-agent to apply the changes:

gpgconf --reload gpg-agent

Git (Coming Soon)

GitHub / GitLab (Coming Soon)

Thunderbird

OpenPGP Email Encryption with Thunderbird | nitrokey.com

Git-Tower and Transmit

Git-Tower and Transmit don't have access to the environment variables that are defined in your shell (.zshrc, .profile, ~/.bashrc). Therefore, the environment variable SSH_AUTH_SOCK will still point at the default macOS ssh-agent instead of the gpg-agent.

In Git-Tower you can create a environment.plist file and set the SSH_AUTH_SOCK variable to the right ssh-agent:

Create environment.plist

<!-- https://www.git-tower.com/help/mac/integration/environment -->

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
  <dict>
    <key>SSH_AUTH_SOCK</key>
    <string>~/.gnupg/S.gpg-agent.ssh</string>
  </dict>
</plist>

mv environment.plist ~/Library/Application Support/com.fournova.Tower3/

After you have moved the file, you need to restart Git-Tower to apply the changes.

The downside of this procedure is, that this is only a solution for Git-Tower. Transmit will still point at the default macOS ssh-agent. A more generic and easier way is to define the IdentityAgent in your .ssh/config like:

Host github.com
  IdentityAgent ~/.gnupg/S.gpg-agent.ssh
  User git
  ...