Shit like this is why building websites is no longer fun for me like it was back in the 90s and 2000s. There's way too much security shit to worry about now.
this post was submitted on 02 Dec 2025
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"You can set up your own email server at home, for fun!"
-- The 90's, Probably.
Lol. I'm kinda sad I missed out on that expressive time of making websites when I was growing up. You're right, now everything is very homogenized and there's a billion botswarms just waiting for you to be 3 seconds late to a security update so they can zombify your site for...
(Flips papers) Crypto somehow... it's always crypto.
Internet crime isn't even cool anymore. Lol
I still think the web would have been better off if certificates were signed and part of a web of trust like in GPG/PGP. It wouldn't stop sites from using trusted CAs to increase their trust levels with browsers, but it would mean that tiny websites wouldn't need to go through layers of mandatory bullshit and inconvenience. Also means that key signers could have meaningful business relationships rather than being some random CA that nobody has a clue about.
3 letter organisms: NSA - CIA. People tend to think that's a conspiracy theory... Even though we have so many real life examples about how the US and the 3 letters agencies have their hands all over the web and privacy and encryption is just a wet dream !
I'm sorry but if you aren't using automated renewals then you are not using let's encrypt the way it's intended to be used. You should take this as an opportunity to get that set up.
Ours is automated, but we incur downtime on the renewal because our org forbids plain http so we have to do TLS-ALPN-01. It is a short downtime. I wish let's encrypt would just allow http challenges over https while skipping the cert validation. It's nuts that we have to meaningfully reply over 80...
Though I also think it's nuts that we aren't allowed to even send a redirect over 80...
Forgive my ignorance but why would that incur a downtime?
The only way I can think of for downtime to happen if you switched certs before the new one was signed (in which case ..don't) or am I missing something?
It also strikes me as weird that LE requires 80 but does allow insecure 443 after a redirect. Why not just do/allow insecure 443 in the first place?
the TLS-ALPN-01 challenge requires a https server that implements generating a self-signed certificate on demand in response to a specific request. So we have to shut down our usual traffic forwarder and let an ACME implementation control the port for a minute or so. It's not a long downtime, but irritatingly awkward to do and can disrupt some traffic on our site that has clients from every timezone so there's no universal '3 in the morning' time, and even then our service is used as part of other clients '3 in the morning' maintenance windows... Folks can generally take a blip in the provider but don't like that we generate a blip in those logs if they connect at just the wrong minute in a month...
As to why not support going straight to 443, don't know why not. I know they did TLS-ALPN-01 to keep it purely as TLS extensions to stay out of the URL space of services which had value to some that liked being able to fully handle it in TLS termination which frequently is nothing but a reverse proxy and so in principle has no business messing with payload like HTTP-01 requires. However for nginx at least this is awkward as nginx doesn't support it.
Hot take: for-profit orgs should be buying TLS certificates from the CA cartel instead of using Let's Encrypt. Unless you're donating to LE, and in that case it's cool.
Frankly, another choice virtually forced by the broader IT.
If the broader IT either provides or brokers a service, we are not allowed to independently spend money and must go through them.
Fine, they will broker commercial certificates, so just do that, right? Well, to renew a certificate, we have to open a ticket and attach our csr as well as a "business justification" and our dept incurs a hundred dollar internal charge for opening that ticket at all. Then they will let it sit for a day or two until one of their techs can get to it. Then we are likely to get feedback about something like their policy changing to forbid EC keys and we must do RSA instead, or vice versa because someone changed their mind. They may email an unexpected manager for confirmation in accordance to some new review process they implemented. Then, eventually, their tech manually renews it with a provider and attaches the certificate to the ticket.
It's pretty much a loophole that we can use let's encrypt because they don't charge and technically the restrictions only come in when purchasing is involved. There was a security guy raising hell that some of our sites used that "insecure" let's encrypt and demanding standards change to explicitly ban them, but the bearaucracy to do that was insurmountable so we continue.
our org forbids plain http
is redirecting http to https also out of the question? because let's encrypt HTTP-01 accepts http -> https redirects:
Our implementation of the HTTP-01 challenge follows redirects, up to 10 redirects deep. It only accepts redirects to “http:” or “https:”, and only to ports 80 or 443. It does not accept redirects to IP addresses. When redirected to an HTTPS URL, it does not validate certificates.
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I've got it setup automated on all my external domains, but trying to automate it on my internal-only domain is rather tedious since not only do I NOT want to open a port for it to confirm, but I have 2 other devices/services on the network not behind my primary reverse proxy that share the same cert.
What In need to do is setup my own custom cron that hits the hosting provider to update the DNS txt entries. Then I need to have it write and restart the services that use the cert. I've tried to automate this once before and it did not go so smoothly so I've been hesitant on wasting time to try it again... But maybe it's time to.
What would be ideal is if I could allow it to be automated just by getting a one time dns approval and storing a local private/public key to prove to them that I'm the owner of the domain or something. Not aware of this being possible though.
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minor panic, oh, "2028".
Might as well adjust the setting now. I had that same feeling for something they changed several years ago and never got around to changing it til all my stuff went down lol.
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So what's the floor here realistically, are they going to lower it to 30 days, then 14, then 2, then 1? Will we need to log in every morning and expect to refresh every damn site cert we connect to soon?
It is ignoring the elephant in the room -- the central root CA system. What if that is ever compromised?
Certificate pinning was a good idea IMO, giving end-users control over trust without these top-down mandated cert update schedules. Don't get me wrong, LetsEncrypt has done and is doing a great service within the current infrastructure we have, but ...
I kind of wish we could just partition the entire internet into the current "commercial public internet" and a new (old, redux) "hobbyist private internet" where we didn't have to assume every single god-damned connection was a hostile entity. I miss the comraderie, the shared vibe, the trust. Yeah I'm old.
Will we need to log in every morning and expect to refresh every damn site cert we connect to soon?
Automate your certificate renewals. You should be automating updates for security anyway.
This is one of the reasons they're reducing the validity - to try and convince people to automate the renewal process.
That and there's issues with the current revocation process (for incorrectly issued certificates, or certificates where the private key was leaked or stored insecurely), and the most effective way to reduce the risk is to reduce how long any one certificate can be valid for.
A leaked key is far less useful if it's only valid or 47 days from issuance, compared to three years. (note that the max duration was reduced from 3 years to 398 days earlier this year).
From https://www.digicert.com/blog/tls-certificate-lifetimes-will-officially-reduce-to-47-days:
In the ballot, Apple makes many arguments in favor of the moves, one of which is most worth calling out. They state that the CA/B Forum has been telling the world for years, by steadily shortening maximum lifetimes, that automation is essentially mandatory for effective certificate lifecycle management.
The ballot argues that shorter lifetimes are necessary for many reasons, the most prominent being this: The information in certificates is becoming steadily less trustworthy over time, a problem that can only be mitigated by frequently revalidating the information.
The ballot also argues that the revocation system using CRLs and OCSP is unreliable. Indeed, browsers often ignore these features. The ballot has a long section on the failings of the certificate revocation system. Shorter lifetimes mitigate the effects of using potentially revoked certificates. In 2023, CA/B Forum took this philosophy to another level by approving short-lived certificates, which expire within 7 days, and which do not require CRL or OCSP support.
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So what's the floor here realistically, are they going to lower it to 30 days, then 14, then 2, then 1?
LE is beta-testing a 7-day validity, IIRC.
Will we need to log in every morning and expect to refresh every damn site cert we connect to soon?
No, those are expected or even required to be automated.
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Reducing the validity timespan will not solve the problem, it only reduces the risk. And how big is that risk really? I'm an amateur and would love to see some real malicious case descriptions that would have been avoided had the certificate been revoked earlier...
Anybody have some pointers?
Terminology: revoked means the issuer of the certificate has decided that the certificate should not be trusted anymore even though it is still valid.
If a attacker gets access to a certificates key, they can impersonate the server until the validity period of the cert runs out or it is revoked by the CA. However ... revocation doesn't work. The revocation lists arent checked by most clients so a stolen cert will be accepted potentially for a very long time.
The second argument for shorter certs is adoption of new technology so certs with bad cryptographic algorithms are circled out quicker.
And third argument is: if the validity is so short you don't want to change the certs manually and automate the process, you can never forget and let your certs expire.
We will probably get to a point of single day certs or even one cert per connection eventually and every step will be saver than before (until we get to single use certs which will probably fuck over privacy)
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It's the "change your password often odyssey" 2.0. If it is safe, it is safe, it doesn't become unsafe after an arbitrary period of time (if the admin takes care and revokes compromised certs). If it is unsafe by design, the design flaw should be fixed, no?
Or am I missing the point?
The point is, if the certificate gets stolen, there's no GOOD mechanism for marking it bad.
If your password gets stolen, only two entities need to be told it's invalid. You and the website the password is for.
If an SSL certificate is stolen, everyone who would potentially use the website need to know, and they need to know before they try to contact the website. SSL certificate revocation is a very difficult communication problem, and it's mostly ignored by browsers because of the major performance issues it brings having to double check SSL certs with a third party.
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Short lifespans are also great when domains change their owner. With a 3 year lifespan, the old owner could possibly still read traffic for a few more years.
When the lifespan ist just 30-90 days, that risk is significatly reduced.
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I've been dreading this switch for months (I still am, but I have been, too!) considering this year and next year will each double the amount of cert work my team has to do. But, I'm hopeful that the automation work I'm doing will pay off in the long run.
Are you not using LE certbot to handle renewals? I can't even imagine doing this manually.
Personally, yes. Everything is behind NPM and SSL cert management is handled by certbot.
Professionally? LOL NO. Shit is manual and usually regulated to overnight staff. Been working on getting to the point it is automated though, but too many bespoke apps for anyone to have cared enough to automate the process before me.
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