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Re:Compromised Microsoft Key: More Impactful Than We Thought by crote on Saturday July 22, 2023 @02:44AM (#36823911)
If these keys are so important, why are they not treated with similar security measures as CA keys?

Why is it just a handful of keys shared by dozens, hundreds, or likely even thousands of servers? Where is the HSM-backed root key, per-DC intermediate, and per-server transient signing key? Where is the certificate revocation list?

Is it even possible to secure a bearer token from an attack like this? Should we go back to a nonce which we present to the originating service to securely retrieve the payload?

Re:Compromised Microsoft Key: More Impactful Than We Thought by vladvasiliu on Saturday July 22, 2023 @03:53AM (#36824308)
It's not clear to me why there aren't more signing keys. After all, the public part is exposed at an URL you can retrieve whenever you're verifying the token.

I've seen service provider implementations where the access token is exchanged for a cookie or other similar token, in which case you can't really do anything about it anymore for the lifetime of the cookie.

But if you're always verifying the access token with a reasonably short cached key list, the service provider should be able to refuse the token reasonably quickly once the key is no longer advertised.

Re:Compromised Microsoft Key: More Impactful Than We Thought by ThomasRooney on Saturday July 22, 2023 @04:28AM (#36824484)
Anecdotally, I ran an experiment with Envoy to see how far the number of signing keys could scale. This was for a B2B “API Key” auth solution; we wanted user keys to be self revocable, but just be a relatively standard JWT format for maintainability. The hypothesis was that, rather than running a whitelist or blacklist, we could improve the security signature by have 1 signing key for each JWT.

When we ran some stress tests, turned out Envoy could happily run with ~300K signing keys in its JWK Set before noticeable service degradation occurred. Even then, by bumping up the memory on the validation servers, there was a small sacrifice of a few ms per extra 100K keys.

This makes me fully agree that, for many applications, there’s probably an opportunity to vastly improve the security surface by bumping up the number of signing keys dramatically.

As long as both Keys and Signing keys define a KID, key verification is prefaced only by a hash table lookup or a tight loop through a keyset to find the appropriate Signing Key, before the slower verification procedure.

Re:Compromised Microsoft Key: More Impactful Than We Thought by vladvasiliu on Saturday July 22, 2023 @08:12AM (#36825553)
I guess 640K keys ought to be enough for anybody (TM)(r) (c)

More seriously, though, I wonder how AzureAD is implemented and how hard it would be to scope keys per tenant, if not per application. If I'm not mistaken, SAML certificates are per application.

Re:Compromised Microsoft Key: More Impactful Than We Thought by specialist on Saturday July 22, 2023 @10:42AM (#36826632)
ELI5, sorry:

Taking your POC just a bit further and you've got the basis for zero trust networking, right?

That's the Future Perfect Correct Answer™, right?

Re:Compromised Microsoft Key: More Impactful Than We Thought by mistrial9 on Saturday July 22, 2023 @11:46AM (#36827216)
zero trust, or zero stability ?
Re:Compromised Microsoft Key: More Impactful Than We Thought by specialist on Saturday July 22, 2023 @12:41PM (#36827666)
Re:Compromised Microsoft Key: More Impactful Than We Thought by rvdginste on Sunday July 23, 2023 @08:22AM (#36834677)
If you want 1 signing key per JWT, you would need to generate a new key pair for each JWT; wouldn’t that be too expensive? Or was the generation included in your tests?
Re:Compromised Microsoft Key: More Impactful Than We Thought by jrockway on Saturday July 22, 2023 @04:20AM (#36824444)
> If these keys are so important, why are they not treated with similar security measures as CA keys?

No incentive, right? If you mess up as a CA, you go out of business because every browser drops you. But if you're an identity provider and you have an incident, maybe 1% of your customers opens an angry support ticket and you give them 5% off their bill next month. So why bother? Are YOU going to move your 100,000 employee organization off of Microsoft because of this? No? Then why would they care at all? They won the sale and you're stuck with what you get.

Here's a list of companies that have gone out of business because they didn't take information security seriously:

<list not found>

Here's a list of billionaires who had to sell their yachts because they didn't prioritize security over other concerns:

<list not found>

Yeah.

Re:Compromised Microsoft Key: More Impactful Than We Thought by fauigerzigerk on Saturday July 22, 2023 @09:58AM (#36826281)
>No incentive, right? If you mess up as a CA, you go out of business because every browser drops you.

Not going out of business is not the only possible incentive though. Security is a pretty key part of the sales pitch of every cloud provider: "We can do this better than your in-house team" they keep saying.

No one is going to move 100,000 employees off Microsoft over this, but what about signing up the next 100,000? Will it impact next quarter's growth figures?

And for the people directly responsible for security at Microsoft breaches like these may be a career risk or at least a huge embarrassment. There will be meetings. People will get blamed. Some will feel they haven't met their own professional standards.

There's no lack of incentives.

Re:Compromised Microsoft Key: More Impactful Than We Thought by mistrial9 on Saturday July 22, 2023 @10:24AM (#36826495)
you claim that contracts at this level are executed on the basis of technical merit?
Re:Compromised Microsoft Key: More Impactful Than We Thought by fauigerzigerk on Saturday July 22, 2023 @11:21AM (#36826981)
I'm not sure I would call it technical merit, but sentiment and reputation do play a role in negotiations. No cloud provider wants to be perceived as having a weakness in terms of security compared to its closest competitors.

There are debates about risks when large companies move to the cloud - in some industries more than in others. Opposing groups within companies as well as competitors' sales people will be looking for weak spots to make their case.

In isolation, incidents like this don't make a difference. If it looks like a pattern that would be bad for business though.

Re:Compromised Microsoft Key: More Impactful Than We Thought by freedude on Tuesday July 25, 2023 @04:20PM (#36868765)
Does Microsoft have a reputation for good security, adequate security or poor security?

How has this affected sales over the years?

I believe they won the PC wars years ago and there has never been a good replacement system with enough customer incentive that met the same price point. It is this cow they continue to milk.

Re:Compromised Microsoft Key: More Impactful Than We Thought by TheNewsIsHere on Saturday July 22, 2023 @12:04PM (#36827384)
I get what you’re saying, but there’s more nuance here. The smaller the business is, the likelier it is to fold within 1-1.5 years if a major compromise. I’m asserting that in the back of some FBI statistics published about BECs awhile back.

I would posit that your first list needs a conditional for “too big to fail”.

Re:Compromised Microsoft Key: More Impactful Than We Thought by DANmode on Saturday July 22, 2023 @06:47PM (#36830691)
The US does not prioritize small business, or sole proprietorships.

Anyone even adjacent to business or finance during COVID could very clearly witness the wealth transfer, and the smaller competitors being swallowed.

Re:Compromised Microsoft Key: More Impactful Than We Thought by TheNewsIsHere on Sunday July 23, 2023 @02:46PM (#36838364)
Did you mean to reply to another comment? I don’t see the correlation between your comment and mine. I didn’t assert the US was small business friendly, just that smaller businesses are much more at risk than it seemed the parent comment acknowledged.

Which I think is an important point because by volume the majority of businesses in the US are small and mid-sized businesses.

Re:Compromised Microsoft Key: More Impactful Than We Thought by DANmode on Saturday July 22, 2023 @06:45PM (#36830679)
> why are they not treated with similar security measures as CA keys?

Well, that's an unintentionally loaded question if I've ever seen one.