about:nerds

For the average furry using encryption and privacy tools means standing on the shoulders of macros. Friendly and helpful macros for the most part, but free spirits who like the GNU prairies better than the backdoored Microsoft® pen. That pen can be more or less patched up against predators, but not against sophisticated attackers or Bill Gates himself.

So why even bother with privacy tools in Windows®? For the same reason as you put a lock on your front door. It won't stop Al Capone, but yellow press reporters... mostly. And maybe even more importantly, with locks on every door criminals will no longer be able to pick valuable targets by just checking for locks. You benefit from the herd.


Usability

Still, macros' tools are not easy to use in a small pen. I certainly paid my dues and here are just a few examples of hilarious realizations after hours on hours of trial and error:
- Restarting your PC after installation will actually solve problems with Gpg4win and Enigmail. It's the 90s all over again.
- The Thunderbird email-client: "Now that this user has downloaded his emails, I'm sure they won't mind me deleting them from the mail-server. Hurr-durr. They could have told me not to during account set-up."
- So to tighten gpg's password management security in Windows® 8.1, I had to create a file named "gpg-agent.conf" containing the lines "max-cache-ttl 5" and "max-cache-ttl-ssh 5" and put it in gpg's home directory in the hidden App-data folder under "C:\Users\USERNAME"? Wouldn't that be something to put in the documentation?
- In order to anonymize your Pidgin chat traffic via an active tor browser, you can change the proxy settings of Pidgin's OTR plug-in to use the "SOCKS5-Proxy" at host address "127.0.0.1" on port "9150". Apparently they thought that was obvious.


Privacy and the authorities

You may wonder if using tools like gpg or tor might attract the attention of law-enforcers or agencies. Personally, I don't think these institutions should be considered a bunch of evil people. They want to do a good job protecting and serving. Of course they hate guys, who abuse anonymity tools to sell drugs online. But they shouldn't resent you for putting your email into a safe envelope.