My setup :

• OSX : 10.8.5
• Apache :

# httpd -V
Server version: Apache/2.2.26 (Unix)
Server built: Dec 10 2013 22:06:35
Server's Module Magic Number: 20051115:33
Server loaded: APR 1.4.5, APR-Util 1.3.12
Compiled using: APR 1.4.5, APR-Util 1.3.12
Architecture: 64-bit
Server MPM: Prefork
 threaded: no
 forked: yes (variable process count)
Server compiled with....
 -D APACHE_MPM_DIR="server/mpm/prefork"
 -D APR_HAS_SENDFILE
 -D APR_HAS_MMAP
 -D APR_HAVE_IPV6 (IPv4-mapped addresses enabled)
 -D APR_USE_FLOCK_SERIALIZE
 -D APR_USE_PTHREAD_SERIALIZE
 -D SINGLE_LISTEN_UNSERIALIZED_ACCEPT
 -D APR_HAS_OTHER_CHILD
 -D AP_HAVE_RELIABLE_PIPED_LOGS
 -D DYNAMIC_MODULE_LIMIT=128
 -D HTTPD_ROOT="/usr"
 -D SUEXEC_BIN="/usr/bin/suexec"
 -D DEFAULT_PIDLOG="/private/var/run/httpd.pid"
 -D DEFAULT_SCOREBOARD="logs/apache_runtime_status"
 -D DEFAULT_LOCKFILE="/private/var/run/accept.lock"
 -D DEFAULT_ERRORLOG="logs/error_log"
 -D AP_TYPES_CONFIG_FILE="/private/etc/apache2/mime.types"
 -D SERVER_CONFIG_FILE="/private/etc/apache2/httpd.conf"

openssl :

# openssl version
OpenSSL 0.9.8y 5 Feb 2013

Generate a self-signed certificate :

As root :

# cd /etc/apache
# mkdir ssl
# cd ssl

# openssl req -new -newkey rsa:2048 -nodes \
 -out www_192_168_90_25_xip_io.csr \
 -keyout www_192_168_90_25_xip_io.key \
 -subj "/C=FR/ST=FRANCE/L=PARIS/O=MyProject/OU=The Team/CN=www.192.168.90.25.xip.io"

# ls -l
 total 16
 -rw-r--r-- 1 root wheel 1050 Apr 1 10:15 www_192_168_90_25_xip_io.csr
 -rw-r--r-- 1 root wheel 1675 Apr 1 10:15 www_192_168_90_25_xip_io.key

# openssl x509 -req -days 730 -in www_192_168_90_25_xip_io.csr -signkey www_192_168_90_25_xip_io.key -out www_192_168_90_25_xip_io.crt
 Signature ok
 subject=/C=FR/ST=FRANCE/L=PARIS/O=MyProject/OU=The Team/CN=www.192.168.90.25.xip.io
 Getting Private key

# ls -l
 total 24
 -rw-r--r-- 1 root wheel 1294 Apr 1 10:23 www_192_168_90_25_xip_io.crt
 -rw-r--r-- 1 root wheel 1050 Apr 1 10:15 www_192_168_90_25_xip_io.csr
 -rw-r--r-- 1 root wheel 1675 Apr 1 10:15 www_192_168_90_25_xip_io.key

Configure Apache

In extra/httpd-ssl.conf add the following NameVirtualHost directive :

NameVirtualHost *:443
 Listen 443

Also configure your default virtualhost :

<VirtualHost _default_:443>
    DocumentRoot "/Users/charles/Sites"
    ServerName localhost:443
    SSLEngine on
    SSLProtocol all -SSLv2
    SSLCipherSuite HIGH:MEDIUM:!aNULL:!MD5
    SSLCertificateFile "/private/etc/apache2/ssl/www_192_168_90_25_xip_io.crt"
    SSLCertificateKeyFile "/private/etc/apache2/ssl/www_192_168_90_25_xip_io.key"
 </VirtualHost>

In httpd.conf enable ssl (by default, it’s commented out) :

Include /private/etc/apache2/extra/httpd-ssl.conf

You can now connect on your https://localhost

To setup a new virtualhost, enable ssl in your vhost directive :

<VirtualHost *:443>
    ServerAlias www.192.168.90.25.xip.io
    DocumentRoot "/Users/charles/Sites/project
    <Directory /Users/charles/Sites/project>
        Options FollowSymLinks Indexes
        AllowOverride All
    </Directory>
    SSLEngine on
    SSLProtocol all -SSLv2
    SSLCipherSuite HIGH:MEDIUM:!aNULL:!MD5
    SSLCertificateFile "/private/etc/apache2/ssl/www_192_168_90_25_xip_io.crt"
    SSLCertificateKeyFile "/private/etc/apache2/ssl/www_192_168_90_25_xip_io.key"
</VirtualHost>