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I would like to monitor an email server - not whether the port is open and receiving, but rather that a "canary" message sent every so often actually arrives somewhere else. I have had a problem with a server getting firewalled off and no one noticing that cron jobs are not coming from the machine for a few weeks. Of course, the machine itself cannot send out a notification if it is having problems, so this requires an outside service. Any ideas?

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Send a message somewhere where you have POP or IMAP access and try to pick it up again with fetchmail.

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That's what I was thinking. The OP needs an email loop test. – joeqwerty Nov 19 '12 at 17:03
Right, I know how it could be done, but I was hoping there's already a service or solution out there rather than rolling my own. – DGM Nov 19 '12 at 17:05

I have written a simple monitoring script in python which supports this.

if you want to roll your own, you could have a look at the source for an example:

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Panopta's (full disclosure: I'm the founder) monitoring offering supports round-trip email checks, which I think would handle the situation you've got. Our monitoring nodes send a test email every few minutes, and then wait to make sure it can be retrieved via POP or IMAP. Alerts can be sent when the delivery fails or the round trip time exceeds a set threshold.

If you'd like to try it out, let me know and we'd be happy to help with the setup.

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