Usually, April is the first person to hear about Mozilla SSH Observatory issues because she's working Observatory stuff a lot more than I. However, these issues generally boil down to one of two areas, which I should just add monitoring to let me know, so I'm the first person to know.
1.) Alert me when the site is not responding (this is usually nginx restarting and failing or a failed lets encrypt renew)
2.) Alert me when the queues are non-zero and not changing (this is usually an indication that something is broken or site abuse)