Hi,
since openssl 1.1.0 it is possible to establish a HTTPs CONNECT connection to a (Web)server behind a http proxy.
Use the following syntax. Do not omit the port at the connect parameter.
michael@debdev ~ # openssl s_client -proxy myProxy.myDomain.org:8080 -connect www.myDomain.org:443 -showcerts
For versions lower then 1.1.0 use proxytunnel to establish a connection to the proxy and open a local socket for the openssl connect.
michael@debdev ~ # proxytunnel -p myProxy.myDomain.org:8080 -d www.myDomain.org:443 -a 44433 michael@debdev ~ # openssl s_client -connect localhost:44433 -showcerts
Michael
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