Most if not all readers of my blog are probably aware of the Lets Encrypt project, which officially exited Beta this month.
For those of you not familiar with it, the basic premise is "It's the goddamn 21st century, and there is no reason every website shouldn't be available over HTTPS. We're giving away certificates for free, and giving you an automated tool to acquire and renew them. You have no more excuses!"
Most of you also know I was originally quite skeptical of this project: I'm not a huge fan of trusting third-party programs with my cryptography, and I like to ensure that I'm maintaining control of the impotant bits (like private keys) at all times. The final implementation however appears to be well-designed and reasonably secure, enough so that I have used it for this year's certificate renewal on bsd-box.net.
What follows is a brief description of the Lets Encrypt process on FreeBSD: Its successes, its failures, and some thiings I may be submitting patches for in the near future.