||Build Your Own Apache Server with mod_perl and mod_ssl|
Response to: Pass phrase.
AFAIK, putting the passphrase in the startup sequence would defeat the purpose of having one in the first place. It's unlikely that you'll be able to do this. You'll either have to start Apache manually, or build a new certificate without a passphrase. I tend to do the latter, since there's no one else who can log in to my system and muck with the server, anyway.