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So my understanding is that Wyden's staff has been bothering the company about this class of vulnerabilities for a while, and the recent recommendations (a blog post explicitly cited in my post) are one output of that.

But I don't really accept this explanation. I always understand that there are legacy deployments and Microsoft needs to support them, but Kerberos-misconfiguration issues are extremely subtle in their implications, and MS should understand that one blog post (or some knowledge base articles) isn't going to get the message across to the hundreds/thousands of AD admins whose networks are currently at risk.

What I think recent versions of the MS software could do: (1) automatically scan configurations for accounts set up this way, (2) be incredibly annoying about changing the configuration (there are a handful of ways to do this that should be workable for many legacy configurations). If admins want to override the annoying and explicit warnings, that would be on them and not MS. As far as I can tell, Microsoft isn't doing this. But if I'm wrong, please let me know.

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I absolutely agree that Microsoft could do better, but they are making progress in removing support entirely for broken (from a security perspective) older protocols such as NTLMv1 (which uses DES as well: more here -- https://bit.ly/crackingntlmv1) and SMB1.

The financial incentives drive Microsoft to support every possible (mis)configuration, forever. It's the tireless work of a few folk at Microsoft like Ned Pyle, Steve Syfus, and Mark Morowczynski that have landed the changes so far.

There could absolutely be a "security check" tool deployed by default with Server 2025 or similar that looks for Kerberoastable user accounts (any account with a ServicePrincipalName is technically Kerberoastable, like computer accounts), AS-REP roastable accounts, weak encryption types, etc. That would probably get more traction than changing defaults out of the box for everyone, as that's another way to phrase "breaking customer environments when they upgrade".

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As an outsider it seems like MS has been much more proactive at moving away from insecure crypto in other places. For example, there was a while where every Windows release would disable some old insecure part of the SMB/CIFS protocol by default while still allowing it to be enabled for backwards compatibility if necessary.

Are they doing the same for AD? From the article it sounds like it falls back to RC4 automatically out of the box. That is something they should have started migrating away from at least a decade ago - gradually, with options for backwards compatibility to support their customers - but the fact that it is enabled by default in 2025 seems insane.

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