I've got the same problem OP has with a freshly generated key and signed cert from wosign.com on OpenBSD 5.7-stable.
The cert/key work fine with nginx, but with httpd the client simply times out when trying to open a session with the server. OpenSSL s_client stops right after connecting to the server: % openssl s_client -connect $host:443 CONNECTED(00000003) Anything else we can give you for debugging? Thanks Henrik