Encrypted email is still a pain
Let me contrast the author&#x27;s experience with my own. Note that I had a brain injury during this process that made me forget scripting and GPG plus hard to learn. I&#x27;m a nice test case for how hard things are. :)<p>So, I looked into GPG. Holy shit there&#x27;s a ton of options and complexity. High-assurance security says subset to minimal thing that works for increased trustworthiness. I noticed it could encrypt files with others&#x27; public keys. The person that contacted me was able to receive attached files. Text editors only have so many 0-days left in them &amp; are easy to sandbox. So, I decided on this protocol:<p>1. Type the message into a text file.<p>2. Type a cryptic command to encrypt it with that public key.<p>3. Attach the file to a message to that person. Optionally doing this on a different box passed through a data diode if I was worried about GPG box compromised. Just using Linux for now.<p>4. Receiving works other way where I download an encrypted file that I run a decryption command on.<p>So, that&#x27;s simple. How to get started and what commands to use? I installed GPG first. One look at the man page made me hit Google instead. I found a cheat sheet, identified the minimal commands necessary, and compared them against the man page. Saw what seemed to be right stuff but that man page was horrible. Looked at a bunch of other sources online with varying trustworthiness to see if they had same commands. Seemed like I had the right ones. I was also warned the key gen phase could take a long time so I just ignored that usability problem that stomped the OP so much. I was warned after all.<p>The key generated. Messages sent and received well. Only thing left was tediously typing my new buddy&#x27;s email into the box with every encryption. As others came up, I was having to remember more email addresses. Time to automate that shit with a front end that worked on any system I needed. Also, without remembering how to program.<p>I recalled Python was easy. So, I&#x27;d need a data structure for a list of (alias, email) pairs, basic operations on text for maybe substitution, input, conditionals, ability to  print them, and spawn function of some kind. Python reference gave me all I need which I tested each to be sure then composed them with tests. End result was a Python script with the list of alias&#x2F;emails in it like a config file where I could just add people to the script itself. Then, I run the script on the text message with it asking which of a listed group of people to send it to. I type in number or name for it to run command automatically. Then, I verify by eye the new file looks like gibberish and attach it to the email.<p>End result was that I had GPG for friends using it, I figured out how to use it with fair degree of trustworthiness, and I automated the annoying part with less than beginner&#x27;s knowledge of scripting. This shows GPG is way less hard than it appears to be. Although I sure could use a great front-end to smooth over all this. I&#x27;m sure any half-ass programmer could create one given what I did in that state. :)