Hello,

I am running Apache 2.2.13 with SSL and SNI enabled

This is what the virtual host portions looks like:

<VirtualHost *:443>
ServerAdmin support@itherd.com
DocumentRoot /srv/www/apps/login.itherd.com/
ServerName login.itherd.com
ErrorLog /var/log/apache2/login.itherd.com-error_log
SSLEngine on
SSLCertificateFile /etc/apache2/ssl.crt/login.itherd.com.crt
SSLCertificateKeyFile /etc/apache2/ssl.key/login.itherd.com.key
<Directory "srv/www/apps/login.itherd.com/">
AllowOverride None
Options ExecCGI
AddHandler cgi-script cgi pl
Order allow,deny
Allow from all
</Directory>
</VirtualHost>

<VirtualHost *:443>
ServerAdmin support@clubherd.com
DocumentRoot /srv/www/apps/app.clubherd.com/
ServerName app.clubherd.com
ErrorLog /var/log/apache2/club.clubherd.com-error_log
SSLEngine on
SSLCertificateFile /etc/apache2/ssl.crt/app.clubherd.com.crt
SSLCertificateKeyFile /etc/apache2/ssl.key/app.clubherd.com.key
<Directory "srv/www/apps/app.clubherd.com/">
AllowOverride None
Options ExecCGI
AddHandler cgi-script cgi pl
Order allow,deny
Allow from all
</Directory>
</VirtualHost>

When I start Apache it ask me for the pass phrase for the second host (both hosts have one)

When I browse to first host it have recognized the loaded its certificate. When I go to the second server I get am untrusted message because it is using the first certificate.

I have found and followed the directions of several web posts:
http://wiki.apache.org/httpd/NameBasedSSLVHostsWithSNI
http://en.gentoo-wiki.com/wiki/Apach..._Virtual_Hosts

Any help is greatly appreciated.

This is because SSL operates at a lower level than the level hostnames/domains names are transmitted at. So the SSL connection is made before the mention of a domain name.

Thus it is commonly know you can't have more than 1 443/HTTPS server on 1 IP address.

The only way to get it working is to, wildcard cert, like I have. A *.domain.com cert, works on many domains then.
See startssl.com

Or get more IP addresses.

HTH