First, do yourself a favor and replace the gpg.conf that came with your app with this: If you have multiple keys, you can set a default with: default-key <key ID> Command line gpg is easy to use. There are a handful of basic commands, and gpg will ask you for any input that it needs if you haven't provided it. I can give you a run down of the basic commands right now. For the commands that require input, you can either specify a file or type/paste stuff directly in the command prompt window. I will use the "gpg" command, but on Windows you'll have to use "gpg.exe". To import a key: gpg --import If you just type that, you'll see a cursor in the command window and can paste the key in the window. After pasting it in, hit CTRL+D. Otherwise you can save the key in a file and specify that: gpg --import buddy.key To print out your public key, so you can give it to other people: gpg --export KEYINFO Where KEYINFO is either the name, email address or key ID. gpg will search your key ring and use the first match. If it's a long name, you only need to supply a part of it, enough that it uniquely matches that key. The previous command will print it in the command window. You can put the output in a file with redirection: gpg --export KEYINFO > pub.key Ok, with the basic importing and exporting out of the way, we're ready to do encryption. The simplest command to encrypt is: gpg -e Yep, that's it. If you don't supply the recipients, it will ask you for them. Just type in some key info, like above, either part of the name, email address, or key ID. You can add as many recipients as you want, and hit enter (blank recipient) to stop adding recipients. Then you'll get a cursor to type your message. and when you're done, hit CTRL+D, and it will spit the encrypted block into the command window. Alternatively you can type your message in a text file and specify that. gpg -e message.txt And you can specify the recipients too, although I'm too lazy to do that and let it prompt me. gpg -r astor -r bedtime666 -e message.txt It will create a file called message.txt.asc which contains the encrypted message. To decrypt a message: gpg -d And you can paste the message in the command window, then hit CTRL+D. Or specify the file: gpg -d encrypted_message.txt That's enough to get you started.