Absolutely! Every time I had to create a CSR and install an SSL certificate on a server (having done it before in the past), I felt repeatedly terribly painful the process was.
You're going to have to renew anyway. Previously you would have to remember to do that once a year, or maybe once every two years. Now let's ignore the security implications of having certificates that are valid for a year for a moment, and just focus on the actual work. Every year, you have to request a new certificate, wait for your certificate authority, upload the new certificate to the server, reload your webserver, check if everything works.
With LE, you do all of that once. You set up the tooling and the cronjob once. You make sure it works once. And you're done. No more hassle.
I'm not claiming these risks are that significant, but given that LE takes just as much time and effort for initial set-up as a standard multi-year cert, if not more, I think the mantra "some risk of failure is more risk of failure than no risk of failure" is something worth baring in mind.
And I'm not convinced having 90 day certs is a huge security win. Not only can someone do a lot of damage in 90 days, but your private key (the important bit) can't be rolled every 90 days anyway without integrating your rollover scripts with your HPKP config. If you botch that then your visitors can't come back to your website until the pin expires. Scary. Site ending scary. And if you're not using HPKP then i'm not even going to debate the security pros and cons.
On remembering to renew certs... there are many many services out there to send you reminders. Pick 2 or 3 and use them all. Or use a CA that sends reminders.
I'm glad LetsEncrypt exists, but let's not treat it like the be-all-and-end-all.
That's why I renew them a week in advance. I set up Nagios checks which alert me when a certificate is not renewed. Those were already in place before LetEncrypt since human error is just as likely as a script breaking.
given that LE takes just as much time and effort for
initial set-up as a standard multi-year cert
It's just going to take a long time to get there :)
It already is. Use a self-signed cert and ask your visitors via a side channel to tick the box to add an exception. That's the security model of SSH, and has the same assurances. It's just a terrible comparison. We can do better.
A better comparison would be with DNSSEC...
The way to simplify TLS deployment, while getting a better level security as DV CAs, would have been DANE. DNSSEC has an unfortunate reputation as being hard to setup ("pdnssec secure-zone mydomain" is not hard), but it also has exactly the same X day rollover key problem to solve as LE. Solving it once instead of twice would have made a lot of sense.
The symmetries between DNSSEC and LetsEncrypt are striking. Your account key is your KSK. Your cert is your ZSK... but instead of your webserver (in DNSSEC, your DNS server) doing rollover for you, you're depending on a pile of scripts, leaning on an already insecure DNS, and setting it up is still, comparatively, a pita.
As the Caddy server linked in another comment shows, nothing in LE requires you to depend on a "pile of scripts" to do roll-over for you, it's just early days.
DNSSEC puts the CA monopoly in the DNS. There is no API for a hypothetical web server using DANE, because there's no need for periodic domain validation. Of course, DNSSEC is a disaster, so it's a non-starter... but I'm still going to lament the fact that everything is terrible.
Don't do this. If you have to ask your users to add an SSL exception you're doing it very wrong.
I run my cron job[1] every hour. It checks for the expiry of my existing set of certificates and has a configurable parameter as to how soon before expiry to renew them.
it's what I do
I know for me, it was a choice between farting around with lets-encrypt for hours, or a $40 wildcard cert. so I went with the $40/year cert instead.
There are just too many choices for lets-encrypt with no super-simple how-to for people who don't know this stuff (like myself).
In the next few months we'll be shipping an Nginx installer plugin and model renewal scripts for operating systems to provide native automated renewal with their packages of the client. Both of those should help to reduce the amount of work for your use case!
I'm thinking the only thing that would really fix this is an nginx module that would automatically fetch certificates for domains when they're first requested via SNI. First hit takes some time, then it's cached and refreshed once a month or something... it would effectively mean 0 configuration SSL for all new domains.
Regarding the 5 requests per week, I believe that's only for repeated re-issuances of the same domain. As long as you cache the certs, then this shouldn't be an issue. Registering new certificates for new domains is limited to 500 per 3 hours: https://community.letsencrypt.org/t/rate-limits-for-lets-enc...
this is too hard: https://antipaucity.com/2016/02/26/automated-lets-encrypt-ss... ?
I wrote a server that does this. Would be happy to have your feedback sometime: https://caddyserver.com - here's how it works with regards to Let's Encrypt certs: https://www.youtube.com/watch?v=OE5UhQGg_Fo&t=32m
To me, the killer feature right now is that I can just drop it in my /usr/bin directory and have a performant HTTP server in the current dir with just one command. I don't use the LE integration (even though I love the feature) because I haven't deployed it in anything outward-facing.
One small nit would be that I'm not very clear on how the LE fetching is done (where all the files are placed). The docs do mention this, but I left with a feeling that I was still not very clear on where the files go after reading it. Other than that, great job on Caddy!
Edit: are there statements where they say they don't intend to implement it ever, or is it just not supported yet and e.g. Microsoft might still implement it later to please some enterprise stakeholder?
Thanks for all the information though! :)
2. If the certificate is ever compromised, you'll have to keep it in the revocation list forever, or replace the entire CA.
(And I hope your CA contains a DNS name restriction.)
This is the most annoying part of using certs for Radius authentication with Android. Either you self-sign a cert and forever get these warnings, or you let someone else sign your cert and then that CA can issue device certs for your domain.
(And then there's the university way of things: just run your own trusted (!) CA ;-) (e.g. in Germany: signed by DFN)
The number of not https wordpress admin pages and plain text ftp logins still in regular use is chilling and directly attributable to this misaligned incentive.
So the customer calls their developer and their developer calls the host and insists it's a server problem and someone spends an hour or more explaining what mixed content is to a developer and how to fix it.
Then someone runs it through the SSLLabs test and decides they don't like seeing RC4 supported. So you provide some warnings regarding it, confirm, and then oblige, but then you get angry, aggressive emails because their entire office uses Windows XP and their website doesn't work.
A company can burn hours on every individual SSL deployment. There's plenty of unfortunate incentives against hosting companies.
I never realized this so clearly, but it's true. The biggest hindrance to security until LE was that certs were expensive and hard to install. I don't think it was so much the former as the latter. I'd gladly pay 10% more for my cert if it meant my server could renew automatically without me touching it at all.
Then again, for small things, like my home computer that I want to access some stuff on but don't want to pay $10 for, self-signed was fine, so I guess the price was a problem, to a degree.