* System libcrypto.dylib and libssl.dylib are used by system ld on MacOS X. [NOTE: This is currently undergoing tests, and may be removed soon] This is really a misfeature in ld, which seems to look for .dylib libraries along the whole library path before it bothers looking for .a libraries. This means that -L switches won't matter unless OpenSSL is built with shared library support. The workaround may be to change the following lines in apps/Makefile.ssl and test/Makefile.ssl: LIBCRYPTO=-L.. -lcrypto LIBSSL=-L.. -lssl to: LIBCRYPTO=../libcrypto.a LIBSSL=../libssl.a It's possible that something similar is needed for shared library support as well. That hasn't been well tested yet. Another solution that many seem to recommend is to move the libraries /usr/lib/libcrypto.0.9.dylib, /usr/lib/libssl.0.9.dylib to a different directory, build and install OpenSSL and anything that depends on your build, then move libcrypto.0.9.dylib and libssl.0.9.dylib back to their original places. Note that the version numbers on those two libraries may differ on your machine. As long as Apple doesn't fix the problem with ld, this problem building OpenSSL will remain as is. * Parallell make leads to errors While running tests, running a parallell make is a bad idea. Many test scripts use the same name for output and input files, which means different will interfere with each other and lead to test failure. The solution is simple for now: don't run parallell make when testing. * Bugs in gcc 3.0 triggered According to a problem report, there are bugs in gcc 3.0 that are triggered by some of the code in OpenSSL, more specifically in PEM_get_EVP_CIPHER_INFO(). The triggering code is the following: header+=11; if (*header != '4') return(0); header++; if (*header != ',') return(0); header++; What happens is that gcc might optimize a little too agressively, and you end up with an extra incrementation when *header != '4'. We recommend that you upgrade gcc to as high a 3.x version as you can.