Install "xcode" from Apple, specifically "gcc" package and BSD SDK; or install "fink". You may need newer zlib library, in Mac OS X 10.3, there is very old version of it. Make sure you got exec right on configure script and self test shell script: chmod +x ./configure ./irc_bot/selftest_eval-test-1.sh Use "--enable-wildcard-bind" argument to "configure" along others. Run configure. Use "--with-gnutls" for GnuTLS library, or "--with-openssl" for OpenSSL library, but not both. Use "--without-pthread" to explicitly disable Posix Threads library (not recommended). Use "--enable-ipv6" to explicitly enable IPv6 support. Use CXXFLAGS="-g -O0" to enable debugging support, e.g.: CXXFLAGS="-g -O0" ./configure --with-openssl --enable-wildcard-bind Run make After successful build, you can run a self-test suite of bot (strongly recommended): make check