The two most common ways I use: 1) I use this the most, since I've already generated a key pair and have the configuration set up to know the default key. To encrypt with default key: gpg --encrypt filename To decrypt with default key to the screen: gpg --decrypt filename (you could | it to less/more if desired) To decrypt to a file: gpg --decrypt f--output savetofilename filename.gpg If you don't want to use keys which use assymetric encryption, you can use a simple passwword which uses symmetric encryption. To encrypt the file doc.txt: gpg --output doc.gpg --symmetric doc.txt To decrypt the file doc.gpg: gpg --output doc.txt --decrypt doc.gpg 2) Another way, right there without any extra installation in OpenBSD, is openssl. To encrypt: openssl enc -des3 -in filename -out filename.des3 To decrypt: openssl enc -des3 -d -in filename.des3 -out filename Some notes on openssl: Don't forget your passphrase and cipher used, e.g., des3. I should be noted these days most people prefer AES or BlowFish over 3DES. All rules for password length/entropy still apply and some, if not most, consider keys far stronger. See openssl(8) for more details. Also see the "-P" switch in rm(1) for deletion of the original, unencrypted file. 3) Here's a simple way to encrypt a file your editing in vim. This taken from vim(1): To encrypt a document with vim open the new or existing file with: vim -x [file] This will prompt you for a passphrase, and only apply the encryption when writing a file. i.e., if you don't save it or write the file it won't be applied. Use any passphrase you like and the file will be encrypted to that string. Anytime you open the file after this, even using the normal open method (vim [file]) it will prompt for the password before showing any file contents.