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CA Root expired on 30 May 2020

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Re: CA Root expired on 30 May 2020

#61

Honestly, certificates should never expire or should expire daily. If certificate revocation works then its pointless to have expiring certs. Its just a mechanism for CAs to seek rent. If certificate revocation doesnt work then certs need to expire super frequently to limit potential damage if compromised. A certificate that expires in 20 years does absolutely nothing for security compared to a certificate that never…

Exactly. Certificate expiration has never really been about security. It's purely for practicality, so that CRLs won't grow without bound. This is especially true now that we have OCSP stapling. From a security perspective, a short-lived certificate is exactly equivalent to a long-lived certificate with mandatory OCSP stapling and a short-lived OCSP response, but the latter is much more complicated. And in this case…

It’s not true that expiration is not about security. Dan Geer’s talk in 1998, noted at https://cseweb.ucsd.edu/~goguen/courses/275f00/geer.html , is just as relevant today in the design of key management systems.

Expiration is not “just” about cryptographic risk either; there are plenty of operational risks. If you’re putting your server on the Internet, and exposing a service, you should be worried about key compromise, whether by hacker or by Heartbleed. Lifetimes are a way of expressing, and managing, that risk, especially in a world where revocation has a host of failure modes (operational, legal/political, interoperability) that may not be desirable.

As for Root expiration, it’s definitely more complicated than being black and white. It’s a question about whether software should fail-secure (fail-closed) or fail-insecure (fail-open). The decision to trust a CA, by a software vendor, is in theory backed by a variety of evidence, such as the CA’s policies and practices, as well as additional evidence such as audits. On expiration, under today’s model, all of those requirements largely disappear; the CA is free to do whatever they want with the key. Rejecting expired roots is, in part, a statement that what is secure now can’t be guaranteed as secure in 5 years, or 10 years, or 6 months, whatever the vendor decides. They can choose to let legacy software continue to work, but insecurely, potentially laying the accidental groundwork for the botnets of tomorrow, or they can choose to have legacy software stop working then, on the assumption that if they were receiving software updates, they would have received an update to keep things working / extend the timer.

Ultimately, this is what software engineering is: balancing these tradeoffs, both locally and in the broader ecosystem, to try and find the right balance.

Re: CA Root expired on 30 May 2020

#62
post #59
post #57

Earlier quoted context omitted.

It's actually worse. The new root (good I believe until 2038) uses the same key as the now expired certificate. It has to or it would not be possible to validate the certificates that were issued. And this new one is a root certificate installed in browsers! What "should" happen is that no certificate should be issued with an expiration date later than the issuing certificate. Then as the issuing certificate gets clo…

Sorry to reply to my own comment. But I want to clarify. Two certificates (at least) expired. The root named "AddTrust External CA Root" and a subordinate certificate with a subject of "USERTrust RSA Certification Authority." Both expired around the same time. The "USERTrust RSA Certification Authority" certificate signed yet another layer of intermediate certificates. The "USERTrust RSA Certification Authority" cert…

There's actually a third certificate for "USERTrust RSA Certification Authority", also using the same key pair, signed by a different root called "AAA Certificate Services". It looks like the intended replacement for the expiring one is this one, rather than the one where it's the root itself.

Re: CA Root expired on 30 May 2020

#63
post #43

This one bit me today and abruptly ended my day at the beach. The certificate reseller advised my customer that it was okay to include the cross-signing cert in the chain, because browsers will automatically ignore it once it expires, and use the Comodo CA root instead. And that was true for browsers I guess. But my customer also has about 100 machines in the field that use cURL to access their HTTPS API endpoint. cU…

Is that a cURL bug?

Re: CA Root expired on 30 May 2020

#64
post #61

Earlier quoted context omitted.

Exactly. Certificate expiration has never really been about security. It's purely for practicality, so that CRLs won't grow without bound. This is especially true now that we have OCSP stapling. From a security perspective, a short-lived certificate is exactly equivalent to a long-lived certificate with mandatory OCSP stapling and a short-lived OCSP response, but the latter is much more complicated. And in this case…

It’s not true that expiration is not about security. Dan Geer’s talk in 1998, noted at https://cseweb.ucsd.edu/~goguen/courses/275f00/geer.html , is just as relevant today in the design of key management systems. Expiration is not “just” about cryptographic risk either; there are plenty of operational risks. If you’re putting your server on the Internet, and exposing a service, you should be worried about key comprom…

I don't see anything about expiration in that talk.

If you don't have a strong revocation system, then your host is vulnerable whether or not you have expiration, since attackers aren't going to wait until the day before your key expires to try to steal it.

In general, when a CA's root certificate expires, it creates a new one and gives it to browser and OS vendors. What's the difference between the CA continuing to guard their old private key, and starting to guard the new private key?

Re: CA Root expired on 30 May 2020

#65
post #61

Earlier quoted context omitted.

Exactly. Certificate expiration has never really been about security. It's purely for practicality, so that CRLs won't grow without bound. This is especially true now that we have OCSP stapling. From a security perspective, a short-lived certificate is exactly equivalent to a long-lived certificate with mandatory OCSP stapling and a short-lived OCSP response, but the latter is much more complicated. And in this case…

It’s not true that expiration is not about security. Dan Geer’s talk in 1998, noted at https://cseweb.ucsd.edu/~goguen/courses/275f00/geer.html , is just as relevant today in the design of key management systems. Expiration is not “just” about cryptographic risk either; there are plenty of operational risks. If you’re putting your server on the Internet, and exposing a service, you should be worried about key comprom…

[deleted]

Re: CA Root expired on 30 May 2020

#66

Surely the current CA paradigm shouldn't continue to be accepted by the people who keep infrastructure running anymore? We need to do something.

At least for many web apps the future is likely automatically created and managed domain validated certificates. Amazon and Azure provide these free of charge and then you have Let’s encrypt.

This does not change the CA paradigm, but removes many operational issues.

Re: CA Root expired on 30 May 2020

#67
post #56

Andrew Ayer has a write-up about this at https://www.agwa.name/blog/post/fixing_the_addtrust_root_exp... At the core, this is not a problem with the server, or the CA, but with the clients. However, servers have to deal with broken clients, so it’s easy to point at the server and say it was broken, or to point at the server and say it’s fixed, but that’s not quite the case. I discussed this some in https://twitter.co…

Andrew Ayer's tip on getting Debian sorted may have saved me hours.

Re: CA Root expired on 30 May 2020

#68
post #38
post #20

Quick reminder from your friendly local SRE: never ever issue certificates that expire on weekends. Make certs expire in the middle of the afternoon on a business day wherever your operators live and work. The cert in question expires at May 30 10:48:38 2020 GMT, which smells suspiciously like a fixed time after the cert was generated, rather than at a well-chosen point in time.

All my applications use a component that watches certs configured (everything in cert and trust store) and returns warning in telemetry from the application if any of the certificates is less than a week from expiration. This is checked periodically while the application runs. This not only makes sure we don't miss expiration but also ensures we don't forget to configure any of the application. We had a situation whe…

[deleted]

Re: CA Root expired on 30 May 2020

#69

Stripe Webhooks are currently failing "for some users" https://twitter.com/stripestatus/status/1266756286734938116 -- some chance that's related. Edit: for https://www.circuitlab.com/ we saw all Stripe webhooks failing from 4:08am through 12:04pm PDT today with "TLS error". Since 12:04pm (5 minutes ago), some webhooks are succeeding and others are still failing. Edit 2: since 12:17pm all webhooks are succeeding again…

For backwards compatibility, I updated our intermediate certificates to provide the AAA Certificate Services signing https://censys.io/certificates/68b9c761219a5b1f0131784474665... to replace the expired 2nd intermediate certificate. (Modifying the "GandiStandardSSLCA2.pem" file in my case.)

Re: CA Root expired on 30 May 2020

#70
post #20

Quick reminder from your friendly local SRE: never ever issue certificates that expire on weekends. Make certs expire in the middle of the afternoon on a business day wherever your operators live and work. The cert in question expires at May 30 10:48:38 2020 GMT, which smells suspiciously like a fixed time after the cert was generated, rather than at a well-chosen point in time.

Also make a Calendar placeholder (like a fake meeting), invite a lot of folks or a distribution list, and turn on an alert for 24 hours ahead.
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