LibreSSL 2.7+ is a big change and it caused a host of issues for me, most of which I've resolved with the patches posted on the LibreSSL wiki at https://wiki.freebsd.org/LibreSSL/2.7, but www/apache24 is still refusing to start post-update (the port was patched for LibreSSL on 24 Mar with 2.4.33)
FreeBSD 10.3-RELEASE-p28 #0 r330946
When I try # apachectl restart I get:
Apache24 will not start:
httpd: Syntax error on line 130 of /usr/local/etc/apache24/httpd.conf: Cannot load libexec/apache24/mod_ssl.so into server: /usr/local/libexec/apache24/mod_ssl.so: Undefined symbol "OPENSSL_malloc_init"
The following innocuous seeming error reported during the build seems relevant
--- mod_ssl.slo ---
mod_ssl.c:404:5: warning: implicit declaration of function 'OPENSSL_malloc_init' is invalid in C99 [-Wimplicit-function-declaration]
mod_ssl.c: ± 405:
/* We must register the library in full, to ensure our configuration
* code can successfully test the SSL environment.
I don't see a declaration in mod_ssl.h. I believe the function is declared in OPENSSL_malloc, e.g. int OPENSSL_malloc_init(void) and that maybe the latest version of LibreSSL replaced the OpenSSL code that contained this declaration without replacing it. Or something like that. Maybe.
Also posted at