On 2021-11-17 at 03:10:13 UTC-0500 (Wed, 17 Nov 2021 09:10:13 +0100)
Hans-Martin Mosner via mailop <h...@heeg.de>
is rumored to have said:

Hi folks,

I'm trying to understand the root causes and vulnerabilities that lead to hacked mailboxes. Currently, we can handle dynamic IP ranges pretty well, and we have an extensive list of network ranges whose owner are spammers or knowingly accept spammers as customers.

So what mainly remains as spam sources are hacked servers/websites, hacked mail accounts, and freemail accounts registered with the purpose of spamming (I'm looking at you, Google).

Here I want to focus on hacked mail accounts. I can think of two major root causes but I have no idea about their relative significance:

 * Easily guessable passwords, with two subcauses for exploits:
o Brute force authentication attempts - I'm seeing them regularly, and the most egregious networks (e.g. 5.188.206.0/24) are fully blocked at our mailserver, but some mailops are less struct about blocking such abusers. o Hashed password data exfiltration and cracking (for example using JtR) these lists - this would work better with weaker password hashing, but with weak passwords and some CPU power it is probably possible even for strong hash
       algorithms.

Who needs to bother with brute force "cracking" when so many passwords are just out there for the taking? Many breaches of user data, even in recent years, have included unhashed passwords. Based on my own informal observations of multiple systems (some production, some more amenable to careful instrumentation...) the constant stream of auth attempts is mostly using username+password combinations that work *somewhere* or that at least have worked at some point in the past. Phishing is also a significant path of compromise, sometimes with very well-crafted phish messages.

* Malware on client machines where passwords are either stored in a password vault, or entered manually.

Theoretically possible. I know this was common in the past, but I don't think it's currently a major activity. Of the users I've dealt with who have had compromises, 0.00% have used a password manager and >90% reused passwords and/or had pathologically weak passwords.

My gut feeling is that some organizations are especially prone to hacked mail accounts. We're seeing lots of south american government agency users, and many accounts at educational institutions. The latter are often hosted using Microsoft O365 services, and I highly suspect that weak passwords for all the freshly created student accounts may be a major cause, although exfiltrated password data may be a possibility, too.

Big and broadly trusted entities are attractive targets, especially if they do some sort of federated authentication. No one is putting effort into making a credible phish for a site with 20 users. In the case of MS365 & Google, they attract a huge flow of phishes and credential-stuffing of all the passwords that attackers find by other means.

So does anyone have pointers to studies analyzing these (and probably more) causes of exploited mail accounts?

No, but I also would be interested in something more rigorous than my hunches and chance observations.

--
Bill Cole
b...@scconsult.com or billc...@apache.org
(AKA @grumpybozo and many *@billmail.scconsult.com addresses)
Not Currently Available For Hire
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