Well, I did a "chown -R lsadm:lsadm /etc/ssl/private" and that let me apply the key.
But now I am getting:
"[SSL] Config SSL Context with Certificate File: /etc/ssl/certs/server.crt and Key File:/etc/ssl/private/server.key get SSL error: error:0906406D
EM routines
EM_def_callback: problems getting password"
and
"[config:server:listener:SSL] failed to start SSL listener on address 192.168.1.238:443!"