On 12/14/22 3:06 PM, Murray S. Kucherawy wrote:
On Tue, Dec 13, 2022 at 5:00 PM Michael Thomas <[email protected]> wrote:

    On 12/13/22 6:35 AM, Murray S. Kucherawy wrote:

    This tactic appears to me to have three problems: (1) negative
    reputations are of little value to receivers, because attackers
    can easily shed them; (2) if I have to remember everything with a
    negative reputation for some undetermined period of time, I now
    have a resource problem; (3) I can just not sign my mail, because
    maybe no reputation is better than a negative one.

    I don't understand #1. As in they can move to another service? Or
    what?

Right.  IP address gets a bad reputation?  Move to another one.  Domain blocklisted?  Register another one. etc.  Any bad reputation is trivially exchanged for a neutral one.  That leaves us in a world where only positive reputations are meaningful, and presumably once you have one you'll work to protect it.

Unless they're running ipv6, that's getting harder and harder to do, of course. And don't DNSBL's also blacklist subnets too? That's certainly not optimal for whoever is hosting them. ipv4 space costs money these days.

    As for 3, it's pretty easy to cons up a new domain with fresh
    neutral reputation and still enjoy the supposed benefit of mail
    being signed for awhile. If you factor SPF in though it probably
    gets harder because now you need not only a new domain, but the
    underlying network connectivity to avoid detection.

Yep, but if a receiver values DKIM more than SPF, for instance, then maybe they're willing to forgive that lack of support.  Maybe the forwarding problem bugs you enough that you're forced into such a position, for instance.

     Which brings up a question: even though they pass on DKIM they
    should fail on SPF, right? For transactional email that seems like
    a big old red flag, right?

Yes, but that doesn't work for all applications or flows.  It depends on what tolerances work for your use case and your users.

It seems to me that the attack is a pretty narrow use case. That is, spam disguised as marketing email. That seems like a use case that SPF covers well. And it would be really suspicious to have a mile long set of RCPT-TO's for that kind of use case where SPF fails, right? And I'm not sure why they would prefer one or the other -- they are just inputs to a larger data set. But if something with good reputation that normally passes SPF too starts sending mail where SPF fails, that's like a red flag, right? Again the ESP use case should be pretty predictable.

Mike
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