Chapter 4. Daily use of GnuPG

Table of Contents
Defining your security needs
Building your web of trust
Using GnuPG legally

GnuPG is a complex tool with technical, social, and legal issues surrounding it. Technically, it has been designed to be used in situations having drastically different security needs. This complicates key management. Socially, using GnuPG is not strictly a personal decision. To use GnuPG effectively both parties communicating must use it. Finally, as of 1999, laws regarding digital encryption, and in particular whether or not using GnuPG is legal, vary from country to country and is currently being debated by many national governments.

This chapter addresses these issues. It gives practical advice on how to use GnuPG to meet your security needs. It also suggests ways to promote the use of GnuPG for secure communication between yourself and your colleagues when your colleagues are not currently using GnuPG. Finally, the legal status of GnuPG is outlined given the current status of encryption laws in the world.

Defining your security needs

GnuPG is a tool you use to protect your privacy. Your privacy is protected if you can correspond with others without eavesdroppers reading those messages.

How you should use GnuPG depends on the determination and resourcefulness of those who might want to read your encrypted messages. An eavesdropper may be an unscrupulous system administrator casually scanning your mail, it might be an industrial spy trying to collect your company's secrets, or it might be a law enforcement agency trying to prosecute you. Using GnuPG to protect against casual eavesdropping is going to be different than using GnuPG to protect against a determined adversary. Your goal, ultimately, is to make it more expensive to recover the unencrypted data than that data is worth.

Customizing your use of GnuPG revolves around four issues:

A well-chosen key size protects you against brute-force attacks on encrypted messages. Protecting your private key prevents an attacker from simply using your private key to decrypt encrypted messages and sign messages in your name. Correctly managing your web of trust prevents attackers from masquarading as people with whom you communicate. Ultimately, addressing these issues with respect to your own security needs is how you balance the extra work required to use GnuPG with the privacy it gives you.

Choosing a key size

Selecting a key size depends on the key. In OpenPGP, a public/private keypair usually has multiple keys. At the least it has a master signing key, and it probably has one or more additional subkeys for encryption. Using default key generation parameters with GnuPG, the master key will be a DSA key, and the subkeys will be ElGamal keys.

DSA allows a key size up to 1024 bits. This is not especially good given today's factoring technology, but that is what the standard specifies. Without question, you should use 1024 bit DSA keys.

ElGamal keys, on the other hand, may be of any size. Since GnuPG is a hybrid public-key system, the public key is used to encrypt a 128-bit session key, and the private key is used to decrypt it. Key size nevertheless affects encryption and decryption speed since the cost of these algorithms is exponential in the size of the key. Larger keys also take more time to generate and take more space to store. Ultimately, there are diminishing returns on the extra security a large key provides you. After all, if the key is large enough to resist a brute-force attack, an eavesdropper will merely switch to some other method for obtaining your plaintext data. Examples of other methods include robbing your home or office and mugging you. 1024 bits is thus the recommended key size. If you genuinely need a larger key size then you probably already know this and should be consulting an expert in data security.

Protecting your private key

Protecting your private key is the most important job you have to use GnuPG correctly. If someone obtains your private key, then all data encrypted to the private key can be decrypted and signatures can be made in your name. If you lose your private key, then you will no longer be able to decrypt documents encrypted to you in the future or in the past, and you will not be able to make signatures. Losing sole possession of your private key is catastrophic.

Regardless of how you use GnuPG you should store the public key's revocation certificate and a backup of your private key on write-protected media in a safe place. For example, you could burn them on a CD-ROM and store them in your safe deposit box at the bank in a sealed envelope. Alternatively, you could store them on a floppy and hide it in your house. Whatever you do, they should be put on media that is safe to store for as long as you expect to keep the key, and you should store them more carefully than the copy of your private key you use daily.

To help safeguard your key, GnuPG does not store your raw private key on disk. Instead it encrypts it using a symmetric encryption algorithm. That is why you need a passphrase to access the key. Thus there are two barriers an attacker must cross to access your private key: (1) he must actually acquire the key, and (2) he must get past the encryption.

Safely storing your private key is important, but there is a cost. Ideally, you would keep the private key on a removable, write-protected disk such as a floppy disk, and you would use it on a single-user machine not connected to a network. This may be inconvenient or impossible for you to do. For example, you may not own your own machine and must use a computer at work or school, or it may mean you have to physically disconnect your computer from your cable modem every time you want to use GnuPG

This does not mean you cannot or should not use GnuPG. It means only that you have decided that the data you are protecting is important enough to encrypt but not so important as to take extra steps to make the first barrier stronger. It is your choice.

A good passphrase is absolutely critical when using GnuPG. Any attacker who gains access to your private key must bypass the encryption on the private key. Instead of brute-force guessing the key, an attacker will almost certainly instead try to guess the passphrase.

The motivation for trying passphrases is that most people choose a passphrase that is easier to guess than a random 128-bit key. If the passphrase is a word, it is much cheaper to try all the words in the dictionaries of the world's languages. Even if the word is permuted, e.g., k3wldood, it is still easier to try dictionary words with a catalog of permutations. The same problem applies to quotations. In general, passphrases based on natural-language utterances are poor passphrases since there is little randomness and lots of redundancy in natural language. You should avoid natural language passphrases if you can.

A good passphrase is one that you can remember but is hard for someone to guess. It should include characters from the whole range of printable characters on your keyboard. This includes uppercase alphabetics characters, numbers, and special characters such as } and |. Be creative and spend a little time considering your passphrase; a good choice is important to ensure your privacy.

Selecting expiration dates and using subkeys

By default, a DSA master signing key and an ElGamal encryption subkey are generated when you create a new keypair. This is convenient, because the roles of the two keys are different, and you may therefore want the keys to have different lifetimes. The master signing key is used to make digital signatures, and it also collects the signatures of others who have confirmed your identity. The encryption key is used only for decrypting encrypted documents sent to you. Typically, a digital signature has a long lifetime, e.g., forever, and you also do not want to lose the signatures on your key that you worked hard to collect. On the other hand, the encryption subkey may be changed periodically for extra security, since if an encryption key is broken, the attacker can read all documents encrypted to that key both in the future and from the past.

It is almost always the case that you will not want the master key to expire. There are two reasons why you may choose an expiration date. First, you may intend for the key to have a limited lifetime. For example, it is being used for an event such as a political campaign and will no longer be useful after the campaign is over. Another reason is that if you lose control of the key and do not have a revocation certificate with which to revoke the key, having an expiration date on the master key ensures that the key will eventually fall into disuse.

Changing encryption subkeys is straightforward but can be inconvenient. If you generate a new keypair with an expiration date on the subkey, that subkey will eventually expire. Shortly before the expiration you will add a new subkey and publish your updated public key. Once the subkey expires, those who wish to correspond with you must find your updated key since they will no longer be able to encrypt to the expired key. This may be inconvenient depending on how you distribute the key. Fortunately, however, no extra signatures are necessary since the new subkey will have been signed with your master signing key, which presumably has already been validated by your correspondents.

The inconvenience may or may not be worth the extra security. Just as you can, an attacker can still read all documents encrypted to an expired subkey. Changing subkeys only protects future documents. In order to read documents encrypted to the new subkey, the attacker would need to mount a new attack using whatever techniques he used against you the first time.

Finally, it only makes sense to have one valid encryption subkey on a keyring. There is no additional security gained by having two or more active subkeys. There may of course be any number of expired keys on a keyring so that documents encrypted in the past may still be decrypted, but only one subkey needs to be active at any given time.

Managing your web of trust

As with protecting your private key, managing your web of trust is another aspect of using GnuPG that requires balancing security against ease of use. If you are using GnuPG to protect against casual eavesdropping and forgeries then you can afford to be relatively trusting of other people's signatures. On the other hand, if you are concerned that there may be a determined attacker interested in invading your privacy, then you should be much less trusting of other signatures and spend more time personally verifying signatures.

Regardless of your own security needs, through, you should always be careful when signing other keys. It is selfish to sign a key with just enough confidence in the key's validity to satisfy your own security needs. Others, with more stringent security needs, may want to depend on your signature. If they cannot depend on you then that weakens the web of trust and makes it more difficult for all GnuPG users to communicate. Use the same care in signing keys that you would like others to use when you depend on their signatures.

In practice, managing your web of trust reduces to assigning trust to others and tuning the options --marginals-needed and --completes-needed. Any key you personally sign will be considered valid, but except for small groups, it will not be practical to personally sign the key of every person with whom you communicate. You will therefore have to assign trust to others.

It is probably wise to be accurate when assigning trust and then use the options to tune how careful GnuPG is with key validation. As a concrete example, you may fully trust a few close friends that you know are careful with key signing and then marginally trust all others on your keyring. From there, you may set --completes-needed to 1 and --marginals-needed to 2. If you are more concerned with security you might choose values of 1 and 3 or 2 and 3 respectively. If you are less concerned with privacy attacks and just want some reasonable confidence about validity, set the values to 1 and 1. In general, higher numbers for these options imply that more people would be needed to conspire against you in order to have a key validated that does not actually belong to the person whom you think it does.