In this case, it's likely that they somehow found the backdoor in SolarWinds' network and realized what was happening that way.
It doesn't take a great deal of sophistication to come up with some of these things, just a bit of cleverness and exposure to the possibility of cleverness.
Then someone realized it was also a good early warning system for new viruses, as many viruses would crash their host process in novel ways that were unlike the usual software-induced errors.
WER reports also could do other things. Sometimes bizarre, impossible crashes would happen. Microsoft would investigate some of these by showing a popup to the user inviting them to participate in analysis. If the user consented, they were put in contact with a Microsoft engineer. Turned out a lot of people were running unstable, overclocked hardware sold to them by vendors who had fraudulently misrepresented the hardware.
The telemetry that is out there is amazing, but not as amazing as the secrets it can reveal.
The original devblog from 2005 is (https://devblogs.microsoft.com/oldnewthing/20050412-47/?p=35...). Aside: Upon pulling that up, I recognized the author as the one who wrote my favorite article about undefined behavior (https://devblogs.microsoft.com/oldnewthing/20140627-00/?p=63...).
[0]: https://www.goodreads.com/book/show/18465875-countdown-to-ze...
But it could go unnoticed and disregarded as completely normal, benign network traffic for years, or perhaps forever.
I frankly don't know how anyone finds any of these sort of burried attacks anymore. When software systems were simpler, it was already difficult to know enough about a system to detect or observe abnormal behavior and that was with simple systems with a fairly deep understanding of how things should be.
Anymore, so many systems are some tower of SaaS APIs mixed with commercial on prem software, then mixed with internal developed software spread across multiple teams, developers with high turnover rates, focus on functional software over specification/documentation for anyone to compare to, etc. that it seems like running over these issues are flukes discovered either by dedicated teams looking only for these issues (security auditing teams) or developers maintaining systems than happen to run across an abnormal behavior in the process of normal maintenance.
Human ingenuity is really impressive sometimes.
Unless the outer layer is a legitimate service that's actually in use, this kind of thing only fools people who'd dismiss this traffic as "something I don't know about, but which is probably benign". Then there's the whole figuring out what IPs this is going to part, which would raise more alarm bells.
Cute, but I think you could do better. Hiding from someone looking at your traffic is very hard. The more important part is how well you hide from dumb automated tools that people rely on for initial detection.
Then again, a huge portion of the auditing/"infosec" market nowadays are untrained random people running automated scanners who actually have zero reverse engineering or proper security research experience, so I'm sure it'd work well against those.
This isn't accurate. If you look at the Snort rules used to block it[1], it is masquerading as traffic to .solarwinds.com (ie, the vendor) to URLs looking like: swip/upd/SolarWinds.CortexPlugin.Components.xml
Unless you knew the software isn't supposed to do that, it isn't suspicious at all.
[1] https://github.com/fireeye/sunburst_countermeasures/blob/mai...
If this were HTTPS then it wouldn't need the obfuscation to pass by undetected. And then there isn't much you could do at that point to find it via traffic analysis, assuming the uncompromised app makes similar HTTPS connections, other than perhaps going deeper into traffic pattern analysis if you're lucky.
Once the threat is identified some other way, it might be possible to develop blocking rules that work at the ciphertext layer (e.g. from packet size patterns exhibited only by the backdoor requests).
It's unclear from that one rule but the majority of the Snort rules for this exploit stop HTTPS. Note the "port 443" in the rules.
A proper analyst working in a well-funded clean environment with carefully defined legitimate traffic patterns. That is not a majority of organizations and it would be very easy to miss something like this in the other 99% where they’re understaffed, dealing with the noise of routine malware, and what appears to be a poorly written vendor application doesn’t stand out as much when you have hundreds of them.