A Geek With Guns

Chronicling the depravities of the State.

Encrypt Everything: OpenPGP

without comments

I firmly believe that all communications should be encrypted. Even if you have nothing to hide you can contribute to the greater good by encrypting your communications. How so? Simple, encrypted communications appear as garbage data to prying eyes that lack the keys necessary to decrypt them. The more encrypted communications flying across the wires the more garbage data prying eyes have to dig through. If all communications were encrypted spies in organizations such as the National Security Agency (NSA) would entirely ineffective.

Tools that enable users to encrypt e-mails have been around for ages but, sadly, few people take advantage of them. In the hopes of alleviating this problem I am going to provide guides to help people get this stuff encrypted. For the first entry in my Encrypt Everything series I’m going to discuss a tool that will allow you to communicate securely over e-mail, OpenPGP.

OpenPGP can be briefly summarized as a software package that allows users to generate public/private key pairs that can be used to securely communicate with other OpenPGP users.

The first question most people are likely to ask is, what the heck is a public/private key pair? Don’t worry, it’s not complicated. Public/private key pairs are used for asymmetric cryptography. Asymmetric cryptography is a fancy way of noting an encryption method that uses two keys, one public and one private. Data encrypted with the private key can only be decrypted with the public key and data encrypted with the public key can only be decrypted with the private key. After generating a public/private key pair you provide your public key to those who want to communicate securely with you. In turn they will provide you with their public key. When they want to send you a secure communication they will encrypt the message with your public key. That message can only be decrypted with your private key, which, as the name implies, is held by only yourself. When you want to reply to the secure communication you encrypt your response with their public key, which can only be decrypted by their private key.

OpenPGP allows you to generate a public/private key pair, encrypt messages with either your private key or another person’s public key, and decrypt messages sent by people who have provided their public key.

An OpenPGP keys looks something like this (which is the public key to blog [at] christopherburg [dot] com):


-----BEGIN PGP PUBLIC KEY BLOCK-----
Version: GnuPG/MacGPG2 v2.0.19 (Darwin)

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=3COR
-----END PGP PUBLIC KEY BLOCK-----

OpenPGP users can use that gobbledygook to encrypt messages that can only be decrypted by me. Generally people also post their public keys to key servers such as the one provided by the Massachusettes Institute of Technology (MIT) or Canonical, the creators of Ubuntu Linux. If you go to either of those key servers and enter my e-mail address into the search box you will be provided with my published public key.

Many OpenPGP applications can be configured to automatically check key servers for public keys. Later in this series, when I cover specific implementations of OpenPGP, I will explain who an e-mail client can automatically search OpenPGP key servers for public keys associated with e-mail addresses that have send OpenPGP encrypted e-mails. Suffice it to say publishing your public key to a key server makes life easier for other OpenPGP users but there is no requirement to do so (OpenPGP is a decentralized system).

OpenPGP public keys can also be signed by other OpenPGP users. When you sign a public key you are verifying that the person who holds the corresponding private key is who he claims to be. This establishes, what is referred to as, a web of trust. What is a web of trust? A web of trust is a decentralized alternative to the chain of trust system most of us use every day.

When you access this site through its secure connection you receive a public key that has been signed by StartCom. StartCom is a certificate authority, which is an organization that signs Secure Socket Layer (SSL) certificates (certificates used to provide secure connections to websites). StartCom’s public signing key is included in most major web browsers and operating systems so whenever you access a site secured by a certificate signed by StartCom your browser will trust it. By signing the certificate StartCom is verifying that your website is who it claims to be (in my case, blog.christopherburg.com). This system is highly centralized since it relies on a handful of certificate authorities.

Returning to the original question, what is a web of trust, the answer is that a web of trust is a system where individuals sign public keys instead of centralized authorities. If I sign your public key anybody who trusts my public key will see that I trust your public key. A person who trusts my judgement of character will then be more inclined to trust that your public key corresponds to a private key in your possession. This system becomes more effective as more people sign your public key, which is why key signing parties exist (yes, us geeks know how to party). When somebody sees your public key has been signed by several people they personally trust they can be reasonably sure that it is your key.

Now you have a general overview of OpenPGP. In the next installment of my Encrypt Everything series I am going to explain how to use GPGTools to encrypt your e-mails with OpenPGP on OS X (Why am I starting with OS X? Because that’s the operating system I generally use for e-mail. Don’t worry, I will cover other tools as the series progresses).

Written by Christopher Burg

May 30th, 2013 at 11:00 am