1. Still WAY too complicated (look at all the stuff you have to know and type)
2. Doesn't seem to support my preferred OS (Windows) or web server (IIS) what-so-ever. Which is strange since, from my experience, installing certs in IIS is already far easier than in Apache and Nginx. (Although maybe that's why they perceive it as less of a priority?)
We've had hundreds of people remark that they found Let's Encrypt faster and easier to use than other CA offerings (though most of those people were using Apache on Debian-based systems), so I think we are getting somewhere. But we definitely hope that upstream web server projects and hosting environments will integrate ACME clients of their own, like Caddy has done, so that eventually most people won't need to run an external client at all and won't have to worry about compatibility or integration problems.
https://community.letsencrypt.org/t/how-letsencrypt-work-for...
The website mentions at the bottom that they're intending to get all of this automated, but they're not at that point yet; they're still in public beta. Certainly all those commands look automatable, just with enough integration with lots of distros / web servers, testing, and debugging. The Let's Encrypt protocol (ACME) is very much designed so that a web server can acquire a certificate with just about no human interaction besides telling it to do so, and keep it up-to-date with no human interaction.
I certainly agree that the instructions on that website are still way too complicated for general use, though far, far simpler than the status quo ante Let's Encrypt.
I didn't realise that people getting SSL certs and administrating servers don't know how to read a literally one-page rundown of what to run. They also have helper scripts to make it much simpler.
> Which is strange since, from my experience, installing certs in IIS is already far easier than in Apache and Nginx. (Although maybe that's why they perceive it as less of a priority?)
nginx literally takes less than 10 minutes to set up not only SSL, but also CSP and several other very important security features.