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SSL certificate requirements are becoming obnoxious

chrislockard.net

241–250 of 305 posts

Re: SSL certificate requirements are becoming obnoxious

#241

Earlier quoted context omitted.

This is what fascinated me too. FWIW the idea of inspecting the certificate "for typos" or similar doesn't make sense. What you're getting from the CA wasn't really the certificate but the act of signing it, which they've already done. Except in some very niche situations your certificate is always already publicly available when you receive it, what you've got back is in some sense a courtesy copy. So it's too late…

It's possible that this was just a slight imprecision of language, and the thing being inspected is the CSR rather than the actual certificate. (But the point about individual certificates/CSRs being unworthy of human attention is totally right.)

There are CAs which to this day have been caught issuing certs that don't match CSRs, because the CA uses a manual process of hand-copy or hand-typing fields from the CSR into the new certificate.

So even reviewing CSRs won't help you.

(The solution of course is to automate your cert request/issuance, which has the side effect of ensuring no human is involved in the cert process)

Re: SSL certificate requirements are becoming obnoxious

#242
post #226

Earlier quoted context omitted.

> I think the most rational takeaway is just that it's too difficult for a typical IT guy to understand, and most SMBs that aren't in tech don't have anyone more knowledgeable on staff. Where would that kind of thinking lead us..? Most medical procedures are too complex for someone untrained to understand. Does that mean clinics should just not offer those procedures anymore, or should they rather make sure to train…

Well I mean there's no inherent requirement that PKI work the way it does. We've mostly just accepted it because it's good enough. Even if your server admins fully understand TLS, there are still issues like clock skew on clients breaking things, old cipher suites needing to be reviewed / sunset, users clicking past certificate warnings despite training, and the list of (sometimes questionable) globally trusted CAs t…

Yeah I have one specific enterprise app (the updater service for another piece of software) that will not work unless TLS 1.1 is turned on at the OS level. It doesn't do anything with it, but some hard coded phone-home function in the software must fire up each time it checks for updates (even though it doesn't use TLS for the connection, but unencrypted FTP) or it will hard fail and not even log the failure.

Re: SSL certificate requirements are becoming obnoxious

#243

Earlier quoted context omitted.

IT serves business needs... not the other way around. If anything, cloud services and mobile device access has made securing anything just about impossible.

Classic case of business not understanding that it doesn't just need access to the data, it needs secure access to the data.

That's what insurance and lawyers are for... so sayeth my management that pay me.

Re: SSL certificate requirements are becoming obnoxious

#244

Since the advent of LetsEncrypt, ACME, and Caddy I haven't thought about SSL/TLS for more than about an hour per year, and that's only because I forget the steps required to setup auto-renewal. I pay nothing, I spend a tiny amount of time dealing with it, and it works brilliantly. I'm not sure why many people are still dealing with legacy manual certificate renewal. Maybe some regulatory requirements? I even have a w…

> Since the advent of LetsEncrypt, ACME, and Caddy I haven't thought about SSL/TLS for more than about an hour per year I run a couple of low-stakes websites just for fun and manually updating certificates takes me about 10 minutes a year, and most of that is remembering how to generate the csr. Setting up an automated process gains me nothing except additional points of failure. Ratcheting the expiration down to 47…

> Ratcheting the expiration down to 47 days is an effort to force everyone to use automation, which makes no sense for small hobby sites.

you make it sound like setting up automated renewals is an onerous process. IME it takes about the same amount of time to set up the automation according to the directions as it does to manually renew the certs with an ACME client. the only difference is you're pasting a command into a crontab/timer instead of directly into your shell to execute.

Re: SSL certificate requirements are becoming obnoxious

#246
post #61

Earlier quoted context omitted.

Why or in which cases is opening a dedicated port better than publishing challenges under some /.well-known path using the standard HTTP port? (You say hijacking the HTTP port, but I don't let the ACME client take over 80/443, I make my reverse proxy point the expected path to a folder the ACME client writes to, I'm not asking for a comparison with a setup where the acme client takes over the reverse proxy and edits…

The case for it is where it's not easy to plop a file in a .well-known path on port 80/443. If you have a reverse proxy that is easy to set up to publish that, that makes it easier. I guess I could have used different wording, I do consider making the .well-known available a subset of hijacking the port, but can see why it would be confusing. ACME setup can still be trickier to set up, but is definitely a good soluti…

ok, thanks!

Re: SSL certificate requirements are becoming obnoxious

#247
Too many people don't realize that it's not an open ecosystem any more. The Web is no longer an open collection of a large number of HTTP/HTML clients and servers. It's a singular platform, produced by control a centralised consortium of a small number of entities (browser vendors (mostly Google), ad vendors (mostly Google), and a few very large for-profit sites (mostly Google)) and since it is their product alone, they dictate how it works and they don't have your interests in mind. You not liking this fact doesn't make it untrue. We're not heading towards this endpoint - we're already there.

You will either obey the rules of the product (as dictated by mostly-Google), or you will stop using the product. It's no different in kind from either obeying the new Play Store policies or getting removed from the Play Store. It's no different in kind from either obeying the new Twitter terms or getting banned from Twitter. These are applications, centrally controlled platforms, not ecosystems.

If the Web decides that you need to meet some requirement but your corporate process is set up in a way that makes it onerous to meet, then you either change your corporate process or you get off the Web.

At least it still doesn't cost actual money or ID documents to be on the Web, like it does on the Play Store. I'm not very sympathetic to corporations who put roadblocks in front of themselves and then play the victim. The Web has demanded that you must have a streamlined fully automated process for certificate issuance and deployment, but, key point, this isn't an unreasonable requirement.

It's justified to keep a close eye on the rollout of new Web requirements, because unreasonable ones are surely not far behind. Google has just announced that in the next version of Android you won't be able to sideload apps that Google hasn't approved. It'd be folly to assume they aren't trying to impose something similar on the Web as well. But this isn't that, and can't become that.

Re: SSL certificate requirements are becoming obnoxious

#248

Since the advent of LetsEncrypt, ACME, and Caddy I haven't thought about SSL/TLS for more than about an hour per year, and that's only because I forget the steps required to setup auto-renewal. I pay nothing, I spend a tiny amount of time dealing with it, and it works brilliantly. I'm not sure why many people are still dealing with legacy manual certificate renewal. Maybe some regulatory requirements? I even have a w…

> Since the advent of LetsEncrypt, ACME, and Caddy I haven't thought about SSL/TLS for more than about an hour per year I run a couple of low-stakes websites just for fun and manually updating certificates takes me about 10 minutes a year, and most of that is remembering how to generate the csr. Setting up an automated process gains me nothing except additional points of failure. Ratcheting the expiration down to 47…

> Ratcheting the expiration down to 47 days is an effort to force everyone to use automation

Forcing everyone to use automation sounds like a great idea. I am sure it is by design.

Re: SSL certificate requirements are becoming obnoxious

#249
post #198
post #173

Earlier quoted context omitted.

I feel like a lot of these requirements need to be really solved from first principles. What do you need these certificates for -- specifically, TLS certificates? If the biggest issue is "we want to encrypt traffic" then the answer really should be something more automated. To put it another way, TLS certificates used to convey a lot of things. We had basic certs that said "you are communicating with the rightful own…

What do I need these certificates for? I need them because browsers have started equating a vanilla http server to a malware-infested North Korean honeypot

Have they? All I see is a little message saying "not secure". They've backtracked from trying to impose a scare screen, and they've even backtracked from displaying a red line through the letters "http".

They've also blocked JavaScript access to things like cameras and microphones if you're not using HTTPS. If it were up to me they'd always block them and you'd have to install an app, but still.

Re: SSL certificate requirements are becoming obnoxious

#250
post #248

Earlier quoted context omitted.

> Since the advent of LetsEncrypt, ACME, and Caddy I haven't thought about SSL/TLS for more than about an hour per year I run a couple of low-stakes websites just for fun and manually updating certificates takes me about 10 minutes a year, and most of that is remembering how to generate the csr. Setting up an automated process gains me nothing except additional points of failure. Ratcheting the expiration down to 47…

> Ratcheting the expiration down to 47 days is an effort to force everyone to use automation Forcing everyone to use automation sounds like a great idea. I am sure it is by design.

This is explicitly the purpose, yes.
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