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I need to monitor a windows box remotely, and if it goes down, I need to receive an email. The catch is that the box needs to reboot nightly, and sometimes during the day as well. So a short downtime of ~5 min or less is fine. But, a longer downtime should trigger an email alert.

I don't want to receive a whole stack of emails if it goes down at night, just one to inform me so I can go bring it back up in the morning. My current thinking involves using net-snmp and rolling my own python script to monitor the box.

This, of course, is reinventing the wheel. But I haven't been able to find any FOSS that does what I want. Either they are more complicated than necessary, or expect you to check their control panel, or don't have an obvious way to monitor if the box is online with the options I want.

I'd like to know if there is a tool I missed, which does what I want. Or failing that, what is considered best practices for this kind of application? Will SNMP provide the info I need, or do I have to do something else? Any gotchas I need to watch out for in the python script?

Alternatives and suggestions welcome, especially if they include links or samples to point me in the right direction.

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All what you want to do can be done by Nagios. It's somewhat overkill for your purpose, but it has good documentation and you can come back here if you have specific questions on how to configure it.

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Do you need to self host it? If yes, Nagios is always a good choice. But if not, I suggest you use a 3rd party website monitoring service. Your requirements are very basic, so you can use the free plan of e. g. AlertFox or Pingdom.

So a short downtime of ~5 min or less is fine. But, a longer downtime should trigger an email alert.

This is a very common requirement. Most monitoring services allow you to define a minimum downtime before an alert is triggered.

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