On 8/29/23 10:46 AM, Charles Mills wrote:
Don't want to get into one of the peeing contests that have become all too common here.

Neither do I.

I do want to have a polite and professional discussion about what things are capable of.

Hopefully I'll learn things from you -- I usually do. :-D Maybe, if I'm very lucky, I'll teach you something. :-)

Let me just say that never mind any enterprise PKI CA constraints, I think Tom was talking about OpenSSL on a PC.

Why elide what is a very germane safety component? That being restricting what a given CA is allowed to sign?

OpenSSL stores private keys -- private keys -- in a pretty accessible format.

OpenSSL /can/ store the private key in a file.

OpenSSL /can/ /also/ depend something like a YubiKey to store the private key.

If I can get into Tom's PC -- perhaps while he is at lunch, or with a clever phish -- and get that private key, then I can generate server certificates for any site in the world and Tom's associates will trust those certificates.

Maybe, maybe not. It will depend if the private key is password protected or not. If there is a password, it won't be a walk up and sign without knowing the password.

Not criticizing Tom or his processes here. Just pointing out to readers that there are some significant risks in general to the approach of "oh, I will just create an ad hoc CA and have my users trust it."

I agree that there are risks.

It's a question of which is more risky long term:

1)  training users to click past certificate warnings
2) the potential for someone to abuse Tom's CA which is constrained to the enterprise domain name and has a hardware token (YubiKey)?

It's all about the lesser of the evils.

Trusting a CA is implicitly trusting everything that anyone does with its root private key.

That's where a constrained CA / root key comes into play.

Trusting the key to sign *. is very bad.

Trusting the key to sign *.example.com, not so much so. Especially if example.com is a private internal domain not possible to use in the real world.

Yes, it is no different in some ways than trusting DigiCert. The difference is that DigiCert has very rigorous protocols for protecting its root private keys. OpenSSL does not.

It's possible for Tom, et al., to make reasonable approximations of what DigiCert, et al., are doing. If Tom's company wanted to, they can purchase a more professional Hardware Security Module (HSM) that can get quite close to what more professional entities do if they so choose.

But using something like a YubiKey to hold the root key of for an enterprise CA constrained to the internal domain is probably reasonably safe. Especially if said YubiKey is used to sign an intermediate certificatte -- like the big kids do -- and storing said YubiKey disconnected, in a safe in between uses once a quarter. Especially if the system that does the signing is disconnected from the network.

I think it's well within reason for individuals, and especially businesses to fairly safely have an (Enterprise) CA that is constrained to their organization.



Grant. . . .

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