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Six day and IP address certificate options in 2025

letsencrypt.org

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Re: Six day and IP address certificate options in 2025

#51
post #41

Earlier quoted context omitted.

Why would that matter? Replacing the cert and sighup'ing nginx or whatever isn't functionally different from doing it in-process.

Oh, my, yes it is :) (I don't have time to elaborate on this again right now, unfortunately.)

You have a link to a previous discussion on this? I'm curious if there is some hidden thing occurring or if just connection resets are happening or something else you are aware of.

Re: Six day and IP address certificate options in 2025

#52
post #21

This will get interesting for many CT transparency monitors which for many are already seeing scalability issues. I am operating https://www.merklemap.com/ and the current scale is already impressive.

What a cool site. For a long time I've been looking for something exactly like this for discovery purposes.

Thank you!

Re: Six day and IP address certificate options in 2025

#53
post #43
post #42

If I wanted to get a cert for an IP address today , what the cheapest CA?

ZeroSSL I think will get you IP certificates with their cheapest plan. (Disclaimer: I work on Caddy, which is a ZeroSSL project; but I do so independently.)

"cheapest" being the free plan, or the cheapest non-free plan?

Re: Six day and IP address certificate options in 2025

#54
IP certs improve a niche but interesting use case for me. I run a domain registrar that implements a simple OAuth2 protocol[0] for delegating domains/subdomains. I also have an open source tunneling tool called boringproxy that implements the client side of this protocol[1].

boringproxy needs to provide a callback redirect_uri to the oauth server in order to retrieve it's token, which it can then use for setting DNS records. However, it can't provide an HTTPS endpoint until it can set up those DNS records and get a cert. Chicken/egg. Currently the spec requires the server to implement a `GET /temp-domain` endpoint which creates a DNS record like 157-245-231-242.example.com which points at the client's IP. This lets boringproxy bootstrap a secure OAuth2 callback endpoint.

IP certs would remove an entire step from this process.

[0]: https://github.com/takingnames/namedrop-protocol-spec

[1]: This is actually broken in boringproxy at the moment, but there's a demo video here: https://www.youtube.com/watch?v=9hf72-fYTts

Re: Six day and IP address certificate options in 2025

#55
post #31

Earlier quoted context omitted.

AFAIK, Caddy is the only integrated ACME client that is tuned for short-lived certificates. All its own self-signed certs are already 24-hour certificates, so 6-day certs will be no problem.

Why would that matter? Replacing the cert and sighup'ing nginx or whatever isn't functionally different from doing it in-process.

As someone who has rolled my own cert updates and used Caddy, I much prefer the Caddy way.

Re: Six day and IP address certificate options in 2025

#56
post #39

Earlier quoted context omitted.

To someone like me with hobby-level serving needs, the 90 day certificate life is pretty inconvenient, despite having automation set up. I run a tiny VPS that hosts basic household stuff like e-mail and a few tiny web sites for people, and letsencrypt/certbot automation around certificate renewal is the only thing that I seem to need to regularly babysit and log in to manually run/fix. Everything else just hums along…

... which means automation was not setup correctly and 90 days is still too long that you just tolerated it. If it was 6 days after a few turns you would have decided "fuck it I'm going to spend time fixing it once and for all".

These are the attitudes we get when we have a WebPKI cabal drunk on power.

Re: Six day and IP address certificate options in 2025

#57

Kinda funny to call the current 90 day certs "long lived". When Let's Encrypted started out more than 10 years ago most certs from major vendors had a 1 year life span. Let's Encrypt was (one of) the first to use drastically shorter life spans, hence all the ACME automation effort.

To someone like me with hobby-level serving needs, the 90 day certificate life is pretty inconvenient, despite having automation set up. I run a tiny VPS that hosts basic household stuff like e-mail and a few tiny web sites for people, and letsencrypt/certbot automation around certificate renewal is the only thing that I seem to need to regularly babysit and log in to manually run/fix. Everything else just hums along…

Let's Encrypt doesn't work great when the Let's Encrypt client software has a bug or is misconfigured (one of those is true for your situation).

I think keeping the validity long just removes incentives for people to bother fixing their setups. We've seen the shift from "Craig needs to spend a few days on certificate renewal every year" to full automation in most environments when the 90 day validity period was introduced, and shortening it to a week will only help further automation.

You'll always have the option to skip the hassle (for a small fee, unless a Let's Encrypt competitor joins the market), but I feel the benefits outweigh the downsides.

I personally would've preferred something like DANE working, but because the best we've got is DNSSEC and most of the internet doesn't even bother implementing that, I doubt we'll ever see that replace the current CA system.

Re: Six day and IP address certificate options in 2025

#58

Earlier quoted context omitted.

To someone like me with hobby-level serving needs, the 90 day certificate life is pretty inconvenient, despite having automation set up. I run a tiny VPS that hosts basic household stuff like e-mail and a few tiny web sites for people, and letsencrypt/certbot automation around certificate renewal is the only thing that I seem to need to regularly babysit and log in to manually run/fix. Everything else just hums along…

For me it's only ever an issue if I stop renewing a domain, which triggers issues somewhere next renewal and now nginx doesn't reload. Other than that, I've never had to babysit certbot. It's just a systemd timer job.

[deleted]

Re: Six day and IP address certificate options in 2025

#59
post #6

I remember being surprised when Cloudflare launched https://1.1.1.1 with a valid cert and I immediately wanted one, but couldn’t find an easy way to get one. I am gonna try to run a DoH resolver on this and see how it goes.

This was a fun conversation.

I remember calling Clint and Jeremy at DigiCert and asking: "hey we have this cool IP address—what are the odds you guys can issue a certificate for it?"

I'm not sure if they had to dust off some code or process to do it, but they got it done really quickly once the demonstration of control was handled.

Re: Six day and IP address certificate options in 2025

#60
This feels like a disaster waiting to happen -- like what happens if (when?) Let's Encrypt suffers a significant outage and sites can't refresh certificates? Do we just tolerate a significant portion of the Internet being down or broken due to expired certificates? And for what tradeoff? A very small amount of extra security? Is this because certificate revocation is a harder problem to solve / implement at Internet scale?
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