Pretty great privacy with PGP smart cards

This guide is intended for readers familiar with using PGP who want to take an extra step in fortifying the security around their private key. Some of these steps also utilize a command-line interface, and it may be helpful to get comfortable with that interface before diving in. For a beginner-friendly introduction to PGP, check out our guide to using Mailvelope.

Where do your PGP keys live?

In our introduction to PGP, we discussed what public and private key encryption are, and how to create a PGP key pair using Mailvelope, a web browser extension available for Chrome and Firefox. While using Mailvelope is the easiest and most accessible way to get started using PGP, there are potential risks when depending on a web browser’s ability to securely store your keys — not to mention with the security of the computer and its operating system.

A key concern with PGP is keeping the private key used to decrypt or sign messages safe. Your PGP private key is made of a small chunk of text in a file on your computer. Unlike modern end-to-end encrypted communication apps such as Signal, PGP’s keys are static — they don’t change.

What does that mean for you? If an adversary gets a hold of your PGP private key, it can be used to decrypt any existing email or files ever encrypted with your public key. The more places with access to your private key, the greater the possibility of it being exfiltrated by a breach in the security mechanisms of your web browser, operating system, or even the computer hardware itself.

In addition to hacking, there’s also the question of where your key files may be copied. For instance, when your private key lives in the cloud, if you’re using a cloud backup service such as Microsoft’s OneDrive or Apple’s iCloud, you’re entrusting its protection to a third party. Similarly, using a PGP key pair on multiple computers introduces additional risk, as that increases the number of places something can go wrong. The risk of your computer itself being seized is also a concern because it may be possible to exfiltrate the private key with forensic tools.

As a more secure alternative, PGP supports “smart card” hardware, which allows you to decrypt and sign files and emails using the tiny chip encased in a supported smart card device without ever having to share the private key with the computer it’s connected to. Unlike a file for a private key on your computer, smart cards are designed to protect their contents in ways that computers can’t. While general-purpose computers are designed to allow an ever-increasing combination of things to happen in their hardware, smart cards are typically designed to only allow a strict set of functions to run in specific secure circumstances. This massively reduces the possibility that your private key will fall into the wrong hands, although the messages you’re decrypting are still being displayed on your computer. So keep your OS and app updates up to speed to help protect them from malware that could try to read your emails and files once they’re decrypted.

Prepare your computer to create a new key

To create and manage a new key pair safely, it’s important to first have a reasonably secure environment. When PGP was initially created, personal computers were truly personal, existing in a more isolated environment where their data storage was usually only shared with another computer when their owners manually and consciously did so.The way our devices in the modern era are designed, however, both local and remote computers now have copies of their contents, with cloud services — or malware — quietly copying files you don’t even see into parts unknown in the cloud.

Your PGP private key is one file that should never exist outside the devices you own and control. To ensure you know exactly where your key is, you should take some precautions against known risk factors.

Make your computer less vulnerable to malware

Malware presents a similar technology risk but with different adversaries. Whereas an unencrypted backup cloud service might create the vulnerability of lawful access to your files, malware presents the risk of unlawful access to your files.

Malware can find its way into your computer through a few different avenues, including unsolicited email attachments, USB drives of mysterious origin, or sketchy downloads. Modern Windows and Mac devices, however, have built-in defenses against the ability for malware to take hold. Every now and then, though, those security mechanisms are found to have vulnerabilities and can be breached. Run your software updates as often as you can.

In theory, an “air gap” computer that only exists offline and never connects to the internet would offer the most complete possible protection against these risks, but creating an air gap is beyond the scope of this guide.

Pause any file syncing or cloud backups while creating a new key

File syncing software such as iCloud or OneDrive, among others, are designed to copy the files you have on your computer into their cloud service, thus giving them the technical ability to access those files. If you use any cloud file sync or backup services, turn them off before going through this guide:

Windows OneDrive users:

• Windows 10 does not, by default, sync OneDrive with the Application Data folder that your keypair resides in. To make sure of this, click on the blue or white OneDrive cloud icon in the Windows notification area and navigate to More > Settings > Backup > Manage Backup. Only the Desktop, Pictures, and Documents folders, and any folders you’ve previously added to OneDrive should appear.

Mac iCloud users:

• Open iCloud by navigating to Apple Menu > System Settings > Internet Accounts > iCloud and turn off “iCloud Drive.” See Apple’s documentation for more details.

There may be other file sync and backup services to turn off sync for, beyond OneDrive or iCloud. Take note of any you may have running on your computer and check their documentation to learn how to turn off or pause them.

Get the prerequisites in place

There are several manufacturers producing smart card devices of every shape, and most don’t even look like cards at all! This guide uses Yubico's YubiKey 4 and was also tested with Nitrokey’s Nitrokey Pro, but the same steps will be similar across other smart card devices that support PGP. PGP, in this case, will come in the form of Gnu Privacy Guard, or GPG, a free, open source implementation of PGP available for Mac, Windows, and Linux. In addition to a smart card device, you’ll also need to download and install this software:

Windows users:

• Download Gpg4win

Mac users:

• Download GPG Suite

The Gpg4win software for Windows and GPG Suite software for Mac are distributed as a direct download rather than through a package repository or app store. Because of this, you may want to manually verify the downloaded file’s integrity using special codes — “checksums" — to make sure it hasn’t been tampered with between you and the website you’re downloading from. One caveat to this process is that, ultimately, the downloaded software and checksum probably came from the same website. Although attacks on websites to modify downloads and checksums are extremely rare, easily detectable, and usually addressed swiftly, they do sometimes happen. It may be advisable to keep an eye open for any news on this kind of attack happening on either the Gpg4win or GPG Suite websites.

Windows users:

• When downloading Gpg4win, under “Get started — your next steps,” you’ll find a “check integrity” link to a page listing all the checksums available, including the SHA-256 checksum for the Gpg4win .exe file you downloaded.

Mac users:

• Near the download link for GPG Suite, you’ll find a link to a SHA-256 checksum for the .pkg file you downloaded.

To learn how to use this SHA-256 checksum, check out our guide on verifying open source software.

Create and back up your key pair

After verifying your download, you’ll want to install the software you downloaded and create a new PGP key pair, if you don’t already have one you want to migrate to a smart card.

Windows users:

• Follow Riseup.net’s instructions to install Gpg4win and create a new key pair in Kleopatra, the part of Gpg4win you’ll be using for this guide.

Mac users:

• Install GPG Suite on your Mac with the default settings and follow its instructions to create a new key pair.

Once your new key pair is created, you’ll want to make a backup copy. While your aim is to have a PGP private key that only exists in your smart card, sometimes smart cards break or need to be replaced with newer hardware, so it’s a good idea to have a backup copy in an offline location, like a USB drive in a locked safe. A password-encrypted USB drive adds an extra layer of protection, and can be created on a Mac with Disk Utility or VeraCrypt on either Windows or Mac. This is a password you should keep in a secure place, like on a piece of paper in the aforementioned safe or in your password manager.

Once you have your USB drive ready, export both your public and private keys to it.

Windows users:

• From Kleopatra, highlight your key pair and select File > Export private certificate. Make sure “ASCII armor” is checked and set the “Output file” to one in your USB drive.
• Highlight your key pair from the list in Kleopatra and click the “Export…” button. Save the file to your USB drive.

Mac users:

• From GPG Keychain, highlight your key pair from the list and click the “Export” button. From the Save dialog, check the “Include secret key in exported file” checkbox and then save the file to your USB drive.

Generate a revocation certificate

In a worst-case scenario, where your PGP private key is compromised, you can use a “revocation certificate” to revoke any copy of your compromised public key uploaded to a PGP key server. A revocation certificate has to be created before you lose your private key and can be safely stored as a regular file on the USB drive where you store your backup key. The revocation certificate can only be used to mark a public key as revoked and cannot be used for signing or decrypting anything, so the risk of compromise for that file is lower than a private key, but still warrants being stored in a USB drive outside your computer.

Windows users:

• From Kleopatra, highlight your key pair and select View > Details. Click “Generate revocation certificate.” Save the certificate file to your USB drive and feel free to make a copy to any location where you’d like to keep a copy.

Mac users:

• From GPG Keychain, highlight your key pair from the list and select Key > Create Revoke Certificate. Save the certificate file to your USB drive and feel free to make a copy to any location where you’d like to keep a copy.

Move your private key to your smart card

Unfortunately, neither Gpg4win nor GPGTools have a modern interface for interacting with smart cards, so you’ll need to use a command line interface, which you briefly previewed when verifying your download’s checksum. The command line interface is unfamiliar to the vast majority of humanity, since it was designed for a time before graphical user interfaces. In order to set up your smart card with PGP, however, you’ll have to use it.

Windows users:

• Open a Command Prompt by navigating to Start > Windows System > Command Prompt.

Mac users:

• Open Terminal by navigating to Applications > Utilities > Terminal.

Once you’re in Command Prompt or Terminal, you’ll be presented with an empty window leading to a blinking “prompt” where you’ll type your commands.

Each “command” is just a line of instructions you type in. After typing a command, press “Enter” or “Return” on your keyboard to run it and the command line will display the result.

Run a preflight check

Plug your new smart card into a free USB slot.

Note for Windows users: The first time you plug in your smart card, Windows will detect it and may try to install the driver software it needs to be able to communicate with it. After Windows is done installing the drivers, you may need to restart your computer before moving on to the next step.

Note for macOS users: MacOS may mistake your smart card for a keyboard. If you see a Keyboard Setup Assistant dialog appear, you can safely close it and move on with the guide.

At the command line, run the “gpg --card-status” command and confirm you can see the smart card is connected and accessible to GPG. The output should be similar to:

Change the smart card default PGP PINs

The Yubikey 4 we are using in this guide has PGP smart card settings that include two default PINs and a Reset Code Option:

PIN: For normal use, “123456” by default.

Admin PIN: For admin privileges, “12345678” by default.

Reset Code: Used in case you lose or forget your PINs and want to perform a reset and start over.

Before setting up the PINs for your smart card, it is important to have a safe place to store them. A password manager will help you generate, store (and label) each of the three PINs (PIN, admin PIN, and reset code) that you'll be setting up. If you take slightly too long to type some of the commands you'll be using, they may "time out" abruptly and force you to start over in entering a new PIN. So it is recommended that you choose these three PINs ahead of time. Write down your PINs (or preferably, store them in your password manager), so you don’t risk forgetting them.

Important note: If you forget your PIN and enter an incorrect PIN when signing or encrypting something more than three times, you will be locked out of your smart card, and you’ll need to use the admin PIN to reset the PIN. If you forget your admin PIN and enter an incorrect admin PIN more than three times, you’ll need to use the reset code to factory-reset the entire smart card (which will wipe any PGP keys you have stored) and start over. If you forget the reset code, you may have to start over with a new smart card.

Don’t forget to save and label your PINs and reset code in your password manager.

The PIN and admin PIN may contain up to 127 characters for the Yubikey 4 or 32 characters for the Nitrokey Pro, and may include these characters:

• numbers
• uppercase English letters
• lowercase English letters
• special characters such as "#$%_&'() and more if they are ASCII standard characters

The risk of a password breach here is substantially lower than one for any of the passwords you use to log into your devices or online services; smart cards are forged with hardware mechanisms that limit the number of incorrect PIN attempts that can be entered. Because of this, the horse race of password cracking can go no further than three attempts at guessing either the PIN or admin PIN. After attempts at gaining access to the PIN and admin PIN fail, the device is locked and its secrets are irreversibly wiped.

The reset code is a less sensitive code, since, while it can wipe the keys off your smart card, it cannot be used to decrypt or sign anything, so feel free to make it something easy to remember.

Now you'll configure the smart card to use the new PINs.

When prompted, you will have to enter the default PIN (regular or admin, respectively) before entering the one you want to replace it with. If you type an incorrect PIN too many times, you will have to reset your smart card and start over.

At the command line, run the “gpg2 --card-edit” command.

Note for Windows users: If you see a “gpg: can’t connect to the agent: IPC connect call failed” error after running “gpg2 --card-edit,” wait a few minutes for the gpg> prompt to appear, type “quit” and hit enter to exit the prompt, then try “gpg2 --card-edit” again.

At the gpg/card> prompt, run “admin” to enable administrative changes to your smart card.

Next, run the “passwd” command, which will present a list of actions you can take.

First, change the admin pin, so run “3.” A prompt will appear asking for the existing, default admin PIN (12345678). Enter that, then enter the PIN you want to change it to in the prompt that follows.

Next, change the user pin, so run “1.” A prompt will appear asking for the existing default PIN (123456). Enter that, then enter the PIN you want to change it to in the prompt that follows.

Finally, change the reset code, so run “4.” You will be asked for the new admin PIN you just set up. Enter that, then enter the reset code you want to set, in the prompt that appears (there’s no default reset code).

Now that the two PINs and reset code are set, run “q” to exit the “passwd” menu.

Finally, exit from the gpg/card> prompt.

Next, you’ll want to move the private key pair you generated earlier into the smart card. You’ll select it by using its unique long key ID, which is made of the last 16 characters in a PGP key’s fingerprint, which is the even longer, mathematically-derived identifier unique for every PGP key, such as "CEC6EF2BBA762BE5C1345C87DF258C11C785858F," which we’ll use as an example.

With the gpg prompt open, run the “toggle” command to allow the ability to edit the key.

Before moving your private key from your computer to your smart card, it’s important to make sure you have the backup copy you made earlier. Once the private key gets into the smart card and the computer’s copy is removed in the process, there’s no way to get it back. This is why it’s important to follow through on the previous steps of making a backup copy.

You’ll notice there are technically two keys listed: a primary key with the same long key ID that the public key has and a subkey with its own long key ID. You’ll need to move both, one at a time, to the smart card.

Select the subkey and move it first. Computers begin counting (if one can call it that) at zero, so for the second key, run “key 1” to select it.

You’ll now notice there is an asterisk “*” in the line identifying the subkey. Now that you have it selected, let’s move it to the smart card by running the “keytocard” command.

The “usage” attribute for this key was set to Encrypt (E) when it was created. Run “2” to select Encryption key.

Next, you’ll move on to the primary key by running “key 0” to select.

When the primary key is selected, no asterisk “*” is displayed. This “design” decision may make it confusing to tell if anything is selected. In this case, the primary key is always selected by default when no subkey is selected otherwise. With the gpg prompt open, run the “keytocard” command and confirm with “y” when asked to.

Run “3” to choose the authentication key, which will give your smart card the ability to sign files and messages.

Finally, run the “save” command to save your changes and exit the gpg prompt.

Congratulations! You now have PGP set up with your smart card. Just like any security practice though, what’s tested in hypothetical scenarios does not always match up with the chaos of reality. Being able to access encrypted messages is ultimately as important as making sure they’re confidential, and in the real world, people sometimes lose physical objects. (Ever lost your wallet?)

If you lose or upgrade your computer

Because your private key is in a separate device and the only other place it exists is in a backup drive somewhere, anyone seizing your computer will not have what they need to decrypt messages or files encrypted with your private key. Chances are, though, you’ll want to use PGP on a replacement computer. Luckily, there are only a few small steps involved:

After re-installing the aforementioned GPG Suite or Gpg4win software again (or restoring it from a backup), re-import your public key from your USB drive backup.

Windows users:

• From Kleopatra, click the “Import” button and navigate to your USB drive. Select the public key file once you find it and click “Open.”

Mac users:

• From GPG Keychain, click the “Import” button and navigate to your USB drive. Select the public key file once you find it and click “Open.”

After this, you’ll want to run a command on the new computer to re-generate the “stubs” that allow your computer’s PGP key ring to interface with your smart card.

Plug in your smart card and run this command:

After running this command, you should see a list of keys on the card.

If you lose your smart card

Although your private key is protected by a PIN code on your smart card, there is still a chance an attacker may correctly guess it, so the standard procedure is to revoke the existing key with the revocation certificate created earlier. After that, you can start this guide over, generate a new key pair, and move it to a new smart card.

If your smart card has been run over by a tank, chewed and scratched by a ferret, or lost at the bottom of the ocean, but not in the hands of a potential adversary, then it may be OK to restore your key pair from the backup USB drive created earlier, then follow the instructions to move it into a new smart card.