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Part 2: PGP

PGP stands for Pretty Good Privacy and has a pretty storied history. The US goverment considered it a crime to teach the system to people outside the US during the 1990s (https://en.wikipedia.org/wiki/Pretty_Good_Privacy). Today, it is still considered a bit arcane to use, but I will do my best to make this simple.

In order to use PGP, you create a pair of "keys". One is your "private key" that you keep to yourself, and the other is your "public key" that you share. You use someone's public key to encrypt a message for them. Only they can use their private key to decrypt and read it.

This is how to use a program called GPG (GNU Privacy Guard, https://www.gnupg.org/) to create a key pair.

1) GPG should already be installed on many Linux distributions. Run

gpg --version

to see if GPG is installed. If you don't see anything, then download GPG from the link above.

2) Generate a public/private key pair. Before you do this, write down a strong passphrase. You will be on a timer to type it in or you will have to start over. This passphrase allows you to use your private key without having to manually type it out, which would take forever. You will also need to provide a "real name" (which can be anything) and an email address. These will show up on your messages created with PGP, but don't actually have to have any connection to your email account or name. In order to generate the key pair, do

gpg --gen-key

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3) On Dino, you should be able to click the top-left hamburger menu to see an "Accounts" option. In your account settings there is a spot that says OpenPGP followed by "Key Publishing Disabled Select Key". Click on that and you will be able to choose your PGP key that you created earlier.

4) If you and a friend both do this, then you can use PGP to message securely on XMPP. On Dino, you must each start a direct conversation with each other by hitting the + button on the menu and then slecting "Start Conversation" and putting in the other person's account name and server. Even though you can talk to each other just from a request one way, you must both do this in order to use PGP.

5) Once you have each requested to message each other, click on the little lock symbol to the right of where you write a message. Select "OpenPGP". Dino will automatically encypt and decrypt messages as appropriate. You will now need to use your passphrase for your PGP key each time you start Dino to read the encrypted messages.

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Part 3: Mobile and beyond

You can do all of this on mobile, too. I found a client called monocles chat (https://f-droid.org/packages/de.monocles.chat/) for Android that supports PGP using an application called OpenKeychain (https://www.openkeychain.org/) for handling keys. You can either generate a key pair on there, or copy the files containing your keys from Linux to your phone and use them there. (I'd avoid posting that private key file to any online storage, so local network is best.)

You can also manually display your public key and encrypt or decrypt messages through the command line with GPG.

There is another option for secure messaging on XMPP called OMEMO which is based on the Signal protocol. I have some concerns about corporation that maintains the Signal app and with the protocol itself. Signal is run by people with heavy ties to the usual sources of power in Silicon Valley, and is being heavily marketed as the "secure messaging app for activists". This central control and marketing sound dubious to me, especially because their emphasis on "forward security" means that you should be generating keys constantly on an internet-connected device. PGP makes it possible to create keys on a machine that never touches the internet again, so you can have some assurance that you're not having your keys read on creation by someone who controls your device.

#Signal

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@caten I've heard people recommend against PGP; my only personal experience with it is that it's hard and confusing, but apparently it's also insecure: https://www.latacora.com/blog/2019/07/16/the-pgp-problem/, https://soatok.blog/2024/11/15/what-to-use-instead-of-pgp/

@olynch @caten I find the tone of many of these articles annoying, but it does seem like their underlying arguments have merit. It seems like the objections to OpenPGP are essentially these:

1. Its basic architecture predates much of the modern research on cryptography, so it embodies many choices that are now regarded as unwise, just as a result of its age.
2. It has attempted to maintain backward compatibility, and that necessarily creates a large attack surface in any software.
3. For reasons of backward comparability and flexibility, it support many options, so it's too easy to select a set of options that are not actually secure.
4. It was designed as a very general tool, but different cryptographic properties are desirable in different contexts, so it is better to use a tool was that designed for the specific context in question.
5. It is based around the use of long-term keys, but the odds of users realistically keeping keys secure long term is low, so this is a bad approach.
6. The trust model (web of trust) is not practically workable, so in practice you won't really have reliable authentication.
7. It's generally a bit too hard to use for the average person, so there isn't wide enough adoption to make it very useful (to wit, though I had OpenPGP setup for years on my email, I could probably count the number of encrypted emails I received on my fingers.

But really the main reason that I would tend toward using other tools, like Signal, is that it seems to be what the vast majority of cryptographers and infosec practitioners advise, and I assume they understand the issues better than I do.

@olynch @caten I personally enjoy monkeying with some of these more complex systems at times, but I also must acknowledge that the practical security of a system is defined by the realistic behavior the humans that use it, and not by what they are capable of on their best day, or even an average day, but how they will behave on their worst day, when they are tired, or in a rush, or distracted. And so to achieve durable, practical security a system must be relatively simple and easy to use.

I also have to acknowledge that a lot of the people who need to use such systems, lawyers, activists, journalists, are not techies who like monkeying with such things, so for that reason it also makes sense to support ecosystems of tools that are simple enough that they can realistically use them.