Aaron Toponce

This year, at SCALE 12x, I'll be hosting the PGP keysigning party. What is a keysigning party, and why should you attend? Maybe this will clear things up.

What is a keysigning party?

A PGP keysigning party is an event where PGP users meet together to exchange identity information and PGP fingerprints. Typically, at a conference such as SCALE 12x, PGP parties are common. The whole idea of the party is to expand the global "Web of Trust". In reality, however, you attend a keysigning party, because you share interests in cryptography, or you are interested in communicating privately with others. Usually, you can expect 10-20 people to attend keysigning parties at Linux conferences, sometimes more, sometimes less.

What is the Web of Trust?

The Web of Trust is just a logical mapping of exchanged identities. When at the keysigning party, you will exchange photo identification with each other as wall as PGP fingerprints. You do this for two reasons, and two reasons only: to verify that you have the correct key and to verify that the owner of that key is who they say they are. That's it. When you leave the party, you will sign every key that you have personally identified. By doing so, you bring that key into your own personal Web of Trust. An arrow from you to them indicates that you have signed their key. If they return the favor, and sign your key, then a return arrow from them to you will result.

It's not too difficult to create a personal Web of Trust that you can view. I have blogged about it in the past at https://pthree.org/2013/03/01/create-your-own-graphical-web-of-trust-updated/. It's interesting to see the large groupings of signatures. It's clear that there was a PGP keysigning party in those large groups.

What do I bring to a keysigning party?

You really only need three things with you when you come to the party:

1. Something to write with, like a pen or pencil.
2. A government issued photo identification at a minimum. Additional identification is appreciated.
3. Your own printout of your PGP key fingerprint

That last item is important. Very important. If you didn't bring item #3, then most PGP keysigning party organizers will not allow you to participate. In order to printout your PGP key fingerprint, run the following command at your terminal:

$ gpg -K --fingerprint

Print that out on a piece of paper, and bring it with you to the party. Some conferences, such as SCALE 12x, will print your PGP fingerprint on your conference badge. This will allow you to sign keys anywhere anytime. All you need to do is verify that the fingerprint on your personal printout matches the fingerprint on the conference badge. Then you may use your conference badge fingerprint at the party.

It's important that you bring your own copy of your PGP key fingerprint, however. The keysigning party organizer will handout a printout of all the PGP key fingerprints for everyone in attendance. This is to verify that the organizer downloaded your correct and current key(s). You will read off your fingerprint from your personal printout, and everyone else will verify the fingerprint on their printout.

What happens before the party?

All that needs to be done, is every attendant must submit their public PGP key to the party organizer. Typically, there is a deadline on when keys can be submitted. It's important that you adhere to that deadline. The party organize then prints out on paper a list of every PGP key fingerprint of those who are attending. If you submit your key late, it will not be on the paper, and as such, many party orgasizers will not let you participate.

What happens at the party?

The key party organizer will pass out sheets of paper with every PGP key fingerprint that has been submitted. Typically, party organizers will also explain the importance of the party, why cryptography, and other things related to crypto. Then, he will explain how the party will proceed, at which point every attendee will read their PGP key fingerprint from their own printout. Everyone else in attendance will verify that the organizer has the correct key by following along on the handout. This is done for everyone in attendance.

After fingerprints have been verified, we then get into two equal lines, facing each other. While facing someone in the line opposite if you, you introduce yourself, explain where your key is on the handout, and exchange government issued identification. After identification has been exchanged, everyone in both lines takes 1/2 step to their right. This will put you in front of a new person to repeat the process. Those at the ends turn around, facing the opposite direction, and continue shuffling to their right. Think of the whole process as one large conveyor belt.

Once you are facing the person you started with, then everyone should have successfully verified everyone else's identity and key. At this point, the party is typically over.

What happens after the party?

This is the most critical step of the whole process, and for some reason, not everyone does it. Now that you have your handout with all the keys printed on it, you need to sign every key that you have personally identified. What you attended was a KEYSIGNING party. This means that you must SIGN KEYS. I know I'm putting a lot of emphasis on this, but I have personally attended close to a dozen PGP keysigning parties, and I would say the rate of signing keys is about 70%, unless I annoy them week in and week out to sign my key, then I'll get a return close to 90%. It blows my mind that people spent a great amount of time at the PGP keysigning party, then don't actually do anything about it.

There are a lot of utilities out there for keysigning party events that make attempts at making the whole process easier. In all reality, the only "difficult" or troublesome part about it is, is converting the fingerprints you have on paper to your computer. Some PGP keysigning organizers will already have a party public keyring, that they will email to those who attended, with only the keys of those that attended. If that's the case, you have it easy. Otherwise, you must do something like the following:

$ gpg --recv-keys 0x<KEYID>

Where "<KEYID>" is the last 16 characters of the person's fingerprint. After you have their public key, then you can sign it with the following command for each key:

$ gpg --default-cert-level 3 --sign-key 0x<KEYID>

It's important that you add the "--default-cert-level 3" as part of the signing process. This certification level says that you have done very careful checking, and you are 100% confident that the key in question belongs to the owner, and that you have personally verified the owner's identity.

After you have signed the key, it is courtesy to email them their public key with your signature. As such, you will need to export their key from your public keyring. You should do this for each key:

$ gpg --armor --output /tmp/0x<KEYID>.asc --export 0x<KEYID>

Attach "/tmp/0x<KEYID>.asc" to your encrypted email, and send it off.

Additional Information

• Should I bring a computer to the keysigning party? No. It's not necessary, and many party organizers consider it a security liability. Things like swapping around USB sticks could infect viruses or other badware. If secret keys are on the computer, it's possible they could be compromised. Even worse, the physical computer itself could get damaged. It's generally best to just leave the computer in your backback or hotel room, and attend the party without it.
• Why should I care about signing PGP keys? Have you ever stopped to think about certificate authorities? When you create an SSL certificate signing request, you ship the CSR off to the CA, along with $200, and they returned a signed key. You then install your key on your web server, and browsers automatically trust data encrypted with it. All because you paid someone money. PGP keys do not have a centralized authority. As such, signing keys is done in an ad hoc manner. Further, money is not exchanged when signing keys. Instead, signing keys is done in person, with face-to-face contact. When you sign a key, you are ultimately saying that you have verified the owner is who they claim to be, and that the key you just signed belongs to them. As a result, a decentralized Web of Trust is built.
• What is the Web of Trust really? The PGP Web of Trust is a decentralized web of connected keys, where the connection is made by cryptographically signing keys. The larger and more connected the Web of Trust is, the stronger the trust becomes for people to send private data to each other within that web. It sounds all geeky and mathematical, but if you just sit back and think about it, it makes sense. No money is involved, like using CAs. No blind trust is involved, such as the behavior of browsers. It's you and me, meeting face-to-face, claiming we are who we say we are, and claiming we own the key we have. Now, after this meeting, I can rest assured that if you send me cryptographically signed data from your key, I know it came from you, and no one else. If you send me encrypted data, I have a copy of your public key, and can decrypt it knowing that you were the one encrypting it. The Web of Trust is just that- establishing trust.
• What is the PGP Strong Set? The largest and most connected Web of Trust is called the PGP Strong Set. There are more keys in this Web of Trust than any other. The way you get into the PGP Strong Set is by having someone in the Strong Set sign your key. A great deal of analysis has been done on the Strong Set. You can read about that analysis at http://pgp.cs.uu.nl/plot/. You can get key statistics such as mean signature distance (MSD), and calculate the distance from one key in the strong set to another key, such as yours that may not be in the strong set. My key, 0x8086060F is in the Strong Set. If ever I am at a keysigning party, and I sign your key, your key will also be included in the Strong Set.