There are the exact same files... the ones in the chrooted environment have been taken from the primary environment: Primary environment: curl is working ./ldd /usr/local/bin/curl /usr/local/bin/curl: libcurl.so.4 => /usr/local/lib/libcurl.so.4 (0x28093000) libssl.so.5 => /usr/local/lib/libssl.so.5 (0x280c8000) libcrypto.so.5 => /usr/local/lib/libcrypto.so.5 (0x28101000) libz.so.3 => /lib/libz.so.3 (0x2821e000) libc.so.6 => /lib/libc.so.6 (0x2822f000) Chrooted environment: Curl is not working %./ldd /usr/local/bin/curl /usr/local/bin/curl: libcurl.so.4 => /usr/local/lib/libcurl.so.4 (0x2808a000) libssl.so.5 => /usr/local/lib/libssl.so.5 (0x280bf000) libcrypto.so.5 => /usr/local/lib/libcrypto.so.5 (0x280f8000) libz.so.3 => /lib/libz.so.3 (0x28215000) libc.so.6 => /lib/libc.so.6 (0x28226000) libssl.so.5 => not found (0x0) libcrypto.so.5 => not found (0x0) executing curl in the chrooted environment gives this: csh: using dumb terminal settings. %curl /libexec/ld-elf.so.1: Shared object "libssl.so.5" not found, required by "libcurl.so.4"