I would like something that gets a list of the websites nginx is serving on a node and checks that they are working.

There does not appear to be an equivalent to Apache's VHOST_DUMP.

Preferably it would do a little more than just a 'ping'. Something a bit more than grabbing a server token. Perhaps following a link or two.

Any chance I can cobble this together from bits and bobs out there? Or is this a start from scratch project? Is it a stupid idea?

I'm pretty sure MONIT will check a nginx process.

I did wonder at the time if I should have explicitly mentioned mmonit. That's what I meant by the server token. Mmonit will check a pid file for a process, or hit a token url. However, the issue is not whether nginx is working, but whether all the sites that nginx should be serving are working. If nginx isn't working at all, then none of the sites will work and everyone will know about it pretty quick.

At work, many of our clients open ping.com accounts for each and every one of their websites and "monitor the servers" that way. I want something similar, but a lot more automated.

Monit can check urls and specific files on urls so if it "Stops working" it will alert you. Works fine for me.

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Is there a way to avoid having to manually update which URLs to check? Otherwise it seems quite a laborious task to update it for sites that come and go.

Well what I do is put each file in a separate config include so if the sites goes I just do rm file.

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Presumably mmonit has some wild card file include syntax. It is still a manual thing to add them in the first place, and update them when they change (which they do!). I see where you are coming from, and it's OK for a site or two, but not something I would realistically commit to it on a larger scale.