While the adoption of OpenPGP by the general population is marginal at best, it is a critical component for the security community and particularly for Linux distributions. For example, every package uploaded into Debian is verified by the central repository using the maintainer's OpenPGP keys and the repository itself is, in turn, signed using a separate key. If upstream packages also use such signatures, this creates a complete trust path from the original upstream developer to users. Beyond that, pull requests for the Linux kernel are verified using signatures as well. Therefore, the stakes are high: a compromise of the release key, or even of a single maintainer's key, could enable devastating attacks against many machines.

That has led the Debian community to develop a good grasp of best practices for cryptographic signatures (which are typically handled using GNU Privacy Guard, also known as GnuPG or GPG). For example, weak (less than 2048 bits) and vulnerable PGPv3 keys were removed from the keyring in 2015, and there is a strong culture of cross-signing keys between Debian members at in-person meetings. Yet even Debian developers (DDs) do not seem to have established practices on how to actually store critical private key material, as we can see in this discussion on the debian-project mailing list. That email boiled down to a simple request: can I have a "key dongles for dummies" tutorial? Key dongles, or keycards as we'll call them here, are small devices that allow users to store keys on an offline device and provide one possible solution for protecting private key material. In this article, I hope to use my experience in this domain to clarify the issue of how to store those precious private keys that, if compromised, could enable arbitrary code execution on millions of machines all over the world.

Why store keys offline?

Before we go into details about storing keys offline, it may be useful to do a small reminder of how the OpenPGP standard works. OpenPGP keys are made of a main public/private key pair, the certification key, used to sign user identifiers and subkeys. My public key, shown below, has the usual main certification/signature key (marked SC) but also an encryption subkey (marked E), a separate signature key (S), and two authentication keys (marked A) which I use as RSA keys to log into servers using SSH, thanks to the Monkeysphere project.

    pub   rsa4096/792152527B75921E 2009-05-29 [SC] [expires: 2018-04-19]
      8DC901CE64146C048AD50FBB792152527B75921E
    uid                 [ultimate] Antoine Beaupré <anarcat@anarc.at>
    uid                 [ultimate] Antoine Beaupré <anarcat@koumbit.org>
    uid                 [ultimate] Antoine Beaupré <anarcat@orangeseeds.org>
    uid                 [ultimate] Antoine Beaupré <anarcat@debian.org>
    sub   rsa2048/B7F648FED2DF2587 2012-07-18 [A]
    sub   rsa2048/604E4B3EEE02855A 2012-07-20 [A]
    sub   rsa4096/A51D5B109C5A5581 2009-05-29 [E]
    sub   rsa2048/3EA1DDDDB261D97B 2017-08-23 [S]

All the subkeys (sub) and identities (uid) are bound by the main certification key using cryptographic self-signatures. So while an attacker stealing a private subkey can spoof signatures in my name or authenticate to other servers, that key can always be revoked by the main certification key. But if the certification key gets stolen, all bets are off: the attacker can create or revoke identities or subkeys as they wish. In a catastrophic scenario, an attacker could even steal the key and remove your copies, taking complete control of the key, without any possibility of recovery. Incidentally, this is why it is so important to generate a revocation certificate and store it offline.

So by moving the certification key offline, we reduce the attack surface on the OpenPGP trust chain: day-to-day keys (e.g. email encryption or signature) can stay online but if they get stolen, the certification key can revoke those keys without having to revoke the main certification key as well. Note that a stolen encryption key is a different problem: even if we revoke the encryption subkey, this will only affect future encrypted messages. Previous messages will be readable by the attacker with the stolen subkey even if that subkey gets revoked, so the benefits of revoking encryption certificates are more limited.

Common strategies for offline key storage

Considering the security tradeoffs, some propose storing those critical keys offline to reduce those threats. But where exactly? In an attempt to answer that question, Jonathan McDowell, a member of the Debian keyring maintenance team, said that there are three options: use an external LUKS-encrypted volume, an air-gapped system, or a keycard.

Full-disk encryption like LUKS adds an extra layer of security by hiding the content of the key from an attacker. Even though private keyrings are usually protected by a passphrase, they are easily identifiable as a keyring. But when a volume is fully encrypted, it's not immediately obvious to an attacker there is private key material on the device. According to Sean Whitton, another advantage of LUKS over plain GnuPG keyring encryption is that you can pass the --iter-time argument when creating a LUKS partition to increase key-derivation delay, which makes brute-forcing much harder. Indeed, GnuPG 2.x doesn't have a run-time option to configure the key-derivation algorithm, although a patch was introduced recently to make the delay configurable at compile time in gpg-agent, which is now responsible for all secret key operations.

The downside of external volumes is complexity: GnuPG makes it difficult to extract secrets out of its keyring, which makes the first setup tricky and error-prone. This is easier in the 2.x series thanks to the new storage system and the associated keygrip files, but it still requires arcane knowledge of GPG internals. It is also inconvenient to use secret keys stored outside your main keyring when you actually do need to use them, as GPG doesn't know where to find those keys anymore.

Another option is to set up a separate air-gapped system to perform certification operations. An example is the PGP clean room project, which is a live system based on Debian and designed by DD Daniel Pocock to operate an OpenPGP and X.509 certificate authority using commodity hardware. The basic principle is to store the secrets on a different machine that is never connected to the network and, therefore, not exposed to attacks, at least in theory. I have personally discarded that approach because I feel air-gapped systems provide a false sense of security: data eventually does need to come in and out of the system, somehow, even if only to propagate signatures out of the system, which exposes the system to attacks.

System updates are similarly problematic: to keep the system secure, timely security updates need to be deployed to the air-gapped system. A common use pattern is to share data through USB keys, which introduce a vulnerability where attacks like BadUSB can infect the air-gapped system. From there, there is a multitude of exotic ways of exfiltrating the data using LEDs, infrared cameras, or the good old TEMPEST attack. I therefore concluded the complexity tradeoffs of an air-gapped system are not worth it. Furthermore, the workflow for air-gapped systems is complex: even though PGP clean room went a long way, it's still lacking even simple scripts that allow signing or transferring keys, which is a problem shared by the external LUKS storage approach.

Keycard advantages

The approach I have chosen is to use a cryptographic keycard: an external device, usually connected through the USB port, that stores the private key material and performs critical cryptographic operations on the behalf of the host. For example, the FST-01 keycard can perform RSA and ECC public-key decryption without ever exposing the private key material to the host. In effect, a keycard is a miniature computer that performs restricted computations for another host. Keycards usually support multiple "slots" to store subkeys. The OpenPGP standard specifies there are three subkeys available by default: for signature, authentication, and encryption. Finally, keycards can have an actual physical keypad to enter passwords so a potential keylogger cannot capture them, although the keycards I have access to do not feature such a keypad.

We could easily draw a parallel between keycards and an air-gapped system; in effect, a keycard is a miniaturized air-gapped computer and suffers from similar problems. An attacker can intercept data on the host system and attack the device in the same way, if not more easily, because a keycard is actually "online" (i.e. clearly not air-gapped) when connected. The advantage over a fully-fledged air-gapped computer, however, is that the keycard implements only a restricted set of operations. So it is easier to create an open hardware and software design that is audited and verified, which is much harder to accomplish for a general-purpose computer.

Like air-gapped systems, keycards address the scenario where an attacker wants to get the private key material. While an attacker could fool the keycard into signing or decrypting some data, this is possible only while the key is physically connected, and the keycard software will prompt the user for a password before doing the operation, though the keycard can cache the password for some time. In effect, it thwarts offline attacks: to brute-force the key's password, the attacker needs to be on the target system and try to guess the keycard's password, which will lock itself after a limited number of tries. It also provides for a clean and standard interface to store keys offline: a single GnuPG command moves private key material to a keycard (the keytocard command in the --edit-key interface), whereas moving private key material to a LUKS-encrypted device or air-gapped computer is more complex.

Keycards are also useful if you operate on multiple computers. A common problem when using GnuPG on multiple machines is how to safely copy and synchronize private key material among different devices, which introduces new security problems. Indeed, a "good rule of thumb in a forensics lab", according to Robert J. Hansen on the GnuPG mailing list, is to "store the minimum personal data possible on your systems". Keycards provide the best of both worlds here: you can use your private key on multiple computers without actually storing it in multiple places. In fact, Mike Gerwitz went as far as saying:

For users that need their GPG key on multiple boxes, I consider a smartcard to be essential. Otherwise, the user is just furthering her risk of compromise.

Keycard tradeoffs

As Gerwitz hinted, there are multiple downsides to using a keycard, however. Another DD, Wouter Verhelst clearly expressed the tradeoffs:

Smartcards are useful. They ensure that the private half of your key is never on any hard disk or other general storage device, and therefore that it cannot possibly be stolen (because there's only one possible copy of it).

Smartcards are a pain in the ass. They ensure that the private half of your key is never on any hard disk or other general storage device but instead sits in your wallet, so whenever you need to access it, you need to grab your wallet to be able to do so, which takes more effort than just firing up GnuPG. If your laptop doesn't have a builtin cardreader, you also need to fish the reader from your backpack or wherever, etc.

"Smartcards" here refer to older OpenPGP cards that relied on the IEC 7816 smartcard connectors and therefore needed a specially-built smartcard reader. Newer keycards simply use a standard USB connector. In any case, it's true that having an external device introduces new issues: attackers can steal your keycard, you can simply lose it, or wash it with your dirty laundry. A laptop or a computer can also be lost, of course, but it is much easier to lose a small USB keycard than a full laptop — and I have yet to hear of someone shoving a full laptop into a washing machine. When you lose your keycard, unless a separate revocation certificate is available somewhere, you lose complete control of the key, which is catastrophic. But, even if you revoke the lost key, you need to create a new one, which involves rebuilding the web of trust for the key — a rather expensive operation as it usually requires meeting other OpenPGP users in person to exchange fingerprints.

You should therefore think about how to back up the certification key, which is a problem that already exists for online keys; of course, everyone has a revocation certificates and backups of their OpenPGP keys... right? In the keycard scenario, backups may be multiple keycards distributed geographically.

Note that, contrary to an air-gapped system, a key generated on a keycard cannot be backed up, by design. For subkeys, this is not a problem as they do not need to be backed up (except encryption keys). But, for a certification key, this means users need to generate the key on the host and transfer it to the keycard, which means the host is expected to have enough entropy to generate cryptographic-strength random numbers, for example. Also consider the possibility of combining different approaches: you could, for example, use a keycard for day-to-day operation, but keep a backup of the certification key on a LUKS-encrypted offline volume.

Keycards introduce a new element into the trust chain: you need to trust the keycard manufacturer to not have any hostile code in the key's firmware or hardware. In addition, you need to trust that the implementation is correct. Keycards are harder to update: the firmware may be deliberately inaccessible to the host for security reasons or may require special software to manipulate. Keycards may be slower than the CPU in performing certain operations because they are small embedded microcontrollers with limited computing power.

Finally, keycards may encourage users to trust multiple machines with their secrets, which works against the "minimum personal data" principle. A completely different approach called the trusted physical console (TPC) does the opposite: instead of trying to get private key material onto all of those machines, just have them on a single machine that is used for everything. Unlike a keycard, the TPC is an actual computer, say a laptop, which has the advantage of needing no special procedure to manage keys. The downside is, of course, that you actually need to carry that laptop everywhere you go, which may be problematic, especially in some corporate environments that restrict bringing your own devices.

Quick keycard "howto"

Getting keys onto a keycard is easy enough:

  1. Start with a temporary key to test the procedure:

        export GNUPGHOME=$(mktemp -d)
        gpg --generate-key
    
  2. Edit the key using its user ID (UID):

        gpg --edit-key UID
    
  3. Use the key command to select the first subkey, then copy it to the keycard (you can also use the addcardkey command to just generate a new subkey directly on the keycard):

        gpg> key 1
        gpg> keytocard
    
  4. If you want to move the subkey, use the save command, which will remove the local copy of the private key, so the keycard will be the only copy of the secret key. Otherwise use the quit command to save the key on the keycard, but keep the secret key in your normal keyring; answer "n" to "save changes?" and "y" to "quit without saving?" . This way the keycard is a backup of your secret key.

  5. Once you are satisfied with the results, repeat steps 1 through 4 with your normal keyring (unset $GNUPGHOME)

When a key is moved to a keycard, --list-secret-keys will show it as sec> (or ssb> for subkeys) instead of the usual sec keyword. If the key is completely missing (for example, if you moved it to a LUKS container), the # sign is used instead. If you need to use a key from a keycard backup, you simply do gpg --card-edit with the key plugged in, then type the fetch command at the prompt to fetch the public key that corresponds to the private key on the keycard (which stays on the keycard). This is the same procedure as the one to use the secret key on another computer.

Conclusion

There are already informal OpenPGP best-practices guides out there and some recommend storing keys offline, but they rarely explain what exactly that means. Storing your primary secret key offline is important in dealing with possible compromises and we examined the main ways of doing so: either with an air-gapped system, LUKS-encrypted keyring, or by using keycards. Each approach has its own tradeoffs, but I recommend getting familiar with keycards if you use multiple computers and want a standardized interface with minimal configuration trouble.

And of course, those approaches can be combined. This tutorial, for example, uses a keycard on an air-gapped computer, which neatly resolves the question of how to transmit signatures between the air-gapped system and the world. It is definitely not for the faint of heart, however.

Once one has decided to use a keycard, the next order of business is to choose a specific device. That choice will be addressed in a followup article, where I will look at performance, physical design, and other considerations.

This article first appeared in the Linux Weekly News.

Created . Edited .