Up to date documentation was near-impossible to find, and the scripts that came out of the box on the recommended client needed some fixing. The whole thing took about half a day, plus some hours a few weeks later once the unforgiving anti-abuse thresholds I accidentally triggered during end-to-end testing finally expired. Definitely wasn't a pleasant experience.
It suddenly becomes really, really complicated if you have multiple servers, multiple domains, nginx configurations that the tool does not expect (but insists on rewriting).
For my part, I had to write around a thousand lines of script and alter various existing code in order to switch from manual ssl (whenever the client paid for it) to automatic ssl (everywhere), because there was no way I was going to manually buy hundreds of certificates a year when I took over this role. Nowadays we're 100% ssl but it was harder for an existing person already accustomed to the existing system than doing nothing. I'm just too lazy to check a site every week and renew many certificates manually and copy around stupid files and generally go crazy. Plus, if it's automated, I think there's less chance of the keys being copied. So in my mind it was worth the effort, but it was surely effort.
It's easy to set up a standard cert through Azure, but if you want to use Let's Encrypt there's a whole dance you have to go through to get there, and for many people it's not worth the time and they'll happily pay a bit of money to make it a few-clicks thing.
Though hopefully they simplify it for cases such as yours.
Putting Cloudflare in front is also another cheap option.
I don't know how it could possibly be any simpler.
Most websites now and days are over engineered.
Most websites now and days are over engineered."
That's awesome! Mind sharing some more details? (hosting plan/CDN/etc). Or even the URL?
Most of our traffic goes to our wiki: we are the most active open source video game on github. Most ss13 servers run their own codebase, forked from ours, but will still frequently point their players to our wiki rather then set one up on their own.
A Cloudflare caching layer was added back in march when we got a 4x spike in web traffic from a youtuber talking about the game.
Then your load balancers pull the current cert from the sidecar every day with NFS/Gluster/Ceph/HTTP/whatver-you-want and reload the web server if it changed.
Assuming that you can catch a failure of your sidecar server in 89 days or so you don't need much more redundancy.
I found that the certs behind a load balancer were enough of a problem that a solution was needed.
For instance Heroku still doesn't provide straightforward support for wildcard domains under SSL: https://devcenter.heroku.com/articles/understanding-ssl-on-h...
There is myriad of other cases, basically every time you diverge a bit from the 80% path, you're in for a treat and will deal with all the intricacies of SSL management.
The end game is first-party support for automatic HTTPS in all web (and other) servers. It is happening (e.g. mod_md), it's just going to take time. For example, to get it packaged for all distributions.
For shared hosting, if you ignore the few providers at the top who are either CAs (e.g. GoDaddy) or are in contracts with CAs (e.g. Namecheap), the overwhelming majority of them are already providing free and automatic SSL for all hosted domains.
There's still a need for certbot et al when you have multiple services (e.g. web and mail and XMPP) running on a single domain name. In fact, I actively avoid servers that insist on doing ACME themselves because it breaks my unified ACME process.
If the middlebox can't see inside your flow because it's encrypted it can't object to whatever new thing it's scared of this time whether that's HD video or a new HTML tag.
For example, I have a simple web app hosted on Heroku free plan, and I have to use CloudFlare SSL to get it served over https on my custom domain. But it actually is half encrypted as the connection between CloudFlare and Heroku is plain http.
https://github.community/t5/GitHub-Pages/Does-GitHub-Pages-S...
My employer won't use Let's Encrypt because they (LE) want unlimited indemnity and that's a deal breaker for them (employer).
What i cannot stand is people who can do it, but refuse to out of laziness. Or because they want their content to be insecure on purpose.
This applies mostly to big orgs, so indie devs can have some leeway if it's too hard to implement.
(Raises guilty hand)
I run a couple of sites on my hosted server that are still http. They both sit behind a varnish setup and to be honest I just have not found the time to get it done. Usually when I mess with my configurations I lose a week to troubleshooting stupid stuff and I just can't bring myself to do it.
Again this really only applies to people in a comfortable position to do this and choose not to. The average developer is not my target here, it's the big guys.
I currently use a mini CDN (content delivery network) of three different OpenVZ servers in the cloud to host my content, so getting things to work with Let’s Encrypt took about two or three days of writing Bash and Ansible scripts which get the challenge-response from Let’s Encrypt, uploading it to all my cloud nodes, having Let’s Encrypt verify it got a good response, uploading the new cert to all of the cloud nodes, then using Ansible to log in to all the nodes, put the new cert where the web server can see it, then restarting the web server.
Point being, the amount of effort needed to get things to work with Let’s Encrypt varies, and can be non-trivial.
Still, the stand-alone mode is pretty dang easy. I've also considered the /.well-known mode but there was some tiny snag.
I'm guessing people aren't as lucky as I am to be running on newer machines and such.
I mean it even edits your nginx files to redirect http to https if you agree. It's not hard.