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I'd advise using Curl to call the web hook from the base monitor machine to check that the target can be hit, and track the request, Curl will give you any error headers if present as well. You can also track the response using Wireshark.
There really isn't anything clever going on within Monitor, it just passes the payload to the given URL. This is almost always an environmental issue - usually firewall.
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Just setting up some slack alerts and managed to get part of the way there, I suspect that there might be a firewall issue with the security settings on my browser but getting the error:
could it be an issue with the https? in https://hooks.slack.com/services/etc
tried different browsers to no avail
How do I trace the issue