Hmmm. Guessing from the output, it looks like the basics (name resolution of AOSMonitor using DNS) is working, which makes me suspect a firewall or proxy server somewhere not allowing you through. You could use your local web browser to try to connect to the Elasticsearch server with HTTPS, but make sure to try it with and without a proxy configuration in the browser, but I really prefer a command line tool for that kind of testing. Do PowerShell come with something that will talk HTTPS? Some type of GetUsingUrl command? If not, install some MinGW tools like curl and wget and thank me later. Cygwin will also do, but might be overkill.