I've found a solution to this problem. You have to use the version of OpenSSL installed on your machine. In my case, it's 0.9.7l (the latest version Apple is supporting). When I tried configuring mod_ssl with SSL_BASE=SYSTEM, it failed saying it couldn't find the OpenSSL libraries. So I grabbed the latest version of OpenSSL (0.9.8g) and compiled against that.
After a lot of digging, I came across this old post (2002) by David Wheeler: http://www.mail-archive.com/modssl-users@modssl.org/msg15623.html This fixed my problem after manually applying the patch. Is there any reason this wasn't applied to mod_ssl 5 years ago or addressed at all? Thanks! Bob [EMAIL PROTECTED] Sent by: [EMAIL PROTECTED] 12/19/2007 09:45 AM Please respond to modssl-users@modssl.org To modssl-users@modssl.org cc Subject mod_ssl-2.8.30-1.3.39 w/ mm-1.4.2 on mac os 10.4 issues Hi, I am trying to run Apache 1.3.39 with mod_ssl 2.8.30, openssl 0.9.8g and mm 1.4.2. I am able to successfully compile it, but when I start Apache in SSL mode, it exits immediately. Looking in the error log, I see the following message: dyld: lazy symbol binding failed: Symbol not found: _SSL_CTX_sess_set_new_cb Referenced from: /usr/local/apache-1.3.39/libexec/libssl.so Expected in: flat namespace Can anyone help me in resolving why this is happening? Thanks, Bob