PGP part 2

How Secure Is It?



If all of this is new to you, you’re likely wondering how secure is the encryption used in PGP. Can we really trust it to protect us from from the NSA and its $52.9 billion black budget? All I can really say is that the cryptographic algorithms used in PGP are all part of the public domain have been heavily vetted by the community of experts. At this point in time there are no feasible attacks known to the general public or academia. It’s certainly possible that the NSA has access to highly advanced math that isn’t publicly known, but even there the best attacks typically don’t reveal the plaintext, rather they just make the keys slightly easier to brute force. The fact that the NSA has pressured Google, Microsoft, Apple etc. into giving them backdoors into their systems seems to be prima facie evidence that they can’t break commercial cryptographic algorithms.

Generating A New Certificate

In PGP a “certificate” is essentially a public key with extra data attached to help others verify that the key really belongs to you. In practice this is usually your name, email address and one or more digital signatures from others (more on that later).

Depending on your operating system, you’ll generate a new certificate by clicking “New”, “New Certificate”, or “New PGP Key”.

At minimum you will have to enter your name, email address, and a strong password that you will use for decrypting and signing data. In the advanced options menu you can select your encryption algorithm (RSA, DSA/ElGamal), key size (in bits), and an expiration date if you want your certificate to expire. The defaults here should suffice for our purposes. The differences are technical and unlikely to affect your overall security (just don’t reduce to the key size).

Once this process is complete you will have generated a new certificate and private key. You can click on “export” to save your public key to a .asc file for distributing to others, or you can copy the text of the key block and share it with people that way.

Key Servers

You might want to consider uploading your public key to a key server such as the MIT Key Server or PGP Global Directory. These are searchable directories from which other people can download your public key without first asking you for it. This functionality comes in especially handy when using email. Some email clients can be configured to search the key servers for the PGP keys of your contacts or anyone who has sent you an encrypted email and import them automatically.

Just keep in mind that once you upload a key to a server, you typically can’t remove it. It’s probably a good idea to play around with PGP first, get used to it, then once you’ve created your permanent key, upload it. That way you don’t litter the key server with multiple keys bearing your name.

Importing Keys

In order to encrypt files to send to others, you will first need to import their public key into PGP. You can do this by downloading the .asc file containing their public key (either directly from others or from a key server), clicking “Import” or “Import Certificate”, and selecting the file. In Linux you can import a key simply by double clicking the .asc file. In Windows you have the option to copy the public key block and import it directly from the clipboard.

The software will typically let you view, edit and sign the public keys on your keyring. More on signing other people’s keys later.

Encrypting Data

You have two options for encrypting data in PGP ― you can encrypt a plain text message from the clipboard or encrypt whole files. Let’s start with encrypting plain text messages. The first thing you need to do is pull up your plain text editor (Notepad in Windows, GNU Emacs works well for this in Linux). You’ll have to forgive me for not being familiar with OS X, but I assume you can encrypt from the clipboard in that operating system (though I’m not positive).

Some things to keep in mind, once you encrypt something with someone else’s public key, you can’t decrypt it. You can, however, encrypt a message using multiple public keys and the message can be decrypted with any of the corresponding private keys. So you could encrypt a message with someone else’s public key and your public key, then you can both decrypt it at a later date. Also, if you encrypt data using only your public key, it basically works like symmetric key encryption in that only you will be able to decrypt it.

To encrypt an entire file select “Sign/Encrypt File” from the menu and select the file you want to encrypt. Just like before, you’ll need to select a public key(s) from your keyring with which to encrypt the file.

PGP part 1

What is PGP?



PGP stands for Pretty Good Privacy. At it’s core, it is an internet standard (called OpenPGP) used for data encryption and digital signatures. Software that employs this standard is available in  free, open source version .



 In conventional encryption, a secret key is used to transform plaintext (the unencrypted data) into unreadable ciphertext. The same key is also used to decrypt the ciphertext and reveal the plaintext. While this process works well for encrypting data stored on your hard drive, it has its drawbacks for use in communication. For one, you need to somehow communicate the secret key to the other party. But how to do this securely? After all, the reason you are using encryption is because you don’t believe your communication channel is secure. You could meet in person and exchange the secret key offline, but that isn’t very convenient. 

Use Cases

 Anyone who has your public key can send you encrypted emails which only you can view. Likewise, you can send encrypted emails to your contacts by first downloading their public keys. In a future post we’ll provide a more thorough tutorial demonstrating how to set up an email client to work with PGP. What you need to keep in mind, however, is only the body of the email will be encrypted. The subject and metadata (to, from, cc, and timestamp) will still be visible to anyone snooping on your emails.

You aren’t limited to just encrypting emails either. Buyers at anonymous marketplaces like Silk Road frequently download their merchant’s public key and use it to encrypt their shipping address so that only the merchant view it. Edward Snowden persuaded journalist Glenn Greenwald to set up PGP prior to leaking the top secret classified documents that revealed the depths of the NSA’s spying operation. You can encrypt whole folders and files with your own public key to protect them from attackers who may gain access to your hard drive. In other words, PGP can be used in just about every conceivable case where strong encryption is needed.

Digital Signatures

A digital signature is created by a mathematical algorithm which combines your private key with data you wish to “sign”. The validity of the signature can by verified by anyone simply by checking it with your public key.

In the above diagram you see that the plaintext is run through a hash function to produce a message digest which is then signed with your private key. What this process ensures is that a signed document cannot be altered without invalidating the signature, allowing people to not only check the document’s authenticity but also the integrity of the data. Just to give an example, suppose you sign a 10,000 word document. If someone were change even a single punctuation in that document, the signature would show as invalid.

Digital signatures are also extremely useful in verifying the integrity of software. A great example here would be Bitcoin wallets. Given the security implications, you want to be able to trust that the wallet you download is legitimate and wont leak information that would allow someone to steal your bitcoins. While all Bitcoin wallets are open source, unless you check and compile the source code yourself, you will most likely download a pre-compiled version that could contain malicious lines of code. Software developers will typically sign the software and provide a link to download the public key used for signing. With Bitcoin-Qt, lead developer Gavin Andresen signs new versions with his PGP key. Simply by checking the signature with his public key you can guarantee you’ve downloaded a legitimate copy.