Back in the days when "system" was a reasonable font choice, fixing a bug after shipping would take weeks, months, or years, and could cost $10^4 to $10^8. You might have had to pull actual boxes off actual shelves somewhere!
In this story as it actually happened, the bug was fixed and the fix was deployed in a single day, at the cost of a few laughs.
I'm sure they tested on Windows when they added Segoe to the list, so the problem is that they didn't test again after fiddling with other fonts that they (incorrectly) thought would be irrelevant to Windows. And remember, nothing was broken in a way that a machine would notice, so automated acceptance tests wouldn't have caught this regression.
I think it's worth considering the possibility that this is a story of Medium acting more or less in their economic interest (maybe even in the economic interest of their users?) rather than a story of a bunch of hipsters with a hilariously broken QC policy.