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Whenever I face a problem like this, I try to narrow it down to a certain layer of the OSI model as quickly as possible. Is DNS resolution working? Yes, so we have an IP address to connect to. Can I ping that address, or is there a network connectivity problem? Am I able to establish a TCP connection to that address/port using telnet?

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Yep. This page describes about half my day job. Our customers will run a windows application on a rather random port, and in the instructions we tell them to open firewall/AWS for it but half the time they forget.

I have a pretty decent powershell script where they put their host name and port and the script will print out what it succeeds at and fails on.

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