We have old Apache + PHP. We can't move to newer versions because of PHP code compatibility issues. But now we neet TLS support, which was not available at previous build time. Let's backup ports tree and install fresh one. Build new OpenSSL and Curl. Rebuild Apache + PHP from old port tree. Restart and see

This happens due to new directory layout in newer port tree. New libs are stored in /usr/local/lib/, but old ones are still in /usr/lib and /usr/lib32. New .h files are at the same location as they were before. Thus, build step is successfull, but further load fails. We must replace old libs with new ones or make symlinks.

/usr/lib/libcrypt.so -> /usr/local/lib/libcrypt.so
/usr/lib/libcrypt.a -> /usr/local/lib/libcrypt.a
/usr/lib/libssl.so -> /usr/local/lib/libssl.so
/usr/lib/libssl.a -> /usr/local/lib/libssl.a

And the same for /usr/lib32. And now rebuild Apache + PHP. Do not run make clean !!!. This may cause rebuild of OpenSSL and Curl from old port tree. Just remove work directory before build.

See also:

• Apache will not start with OpenSSL from ports | The FreeBSD Forums
• Apache22 Undefined symbol "TLSv1_2_server_method"
• Bug #400: Apache will not start with OpenSSL from ports - FreeBSD

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