I downloaded OpenSSL 1.0.1e and tried to build it for both 32-bit and 64-bit with release and debug configurations but it failed on 64-bit debug configuration.
There are only "darwin-i386-cc", "debug-darwin-i386-cc" and "darwin64-x86_64-cc" in 'Configure' of 1.0.1e: ##### MacOS X (a.k.a. Rhapsody or Darwin) setup (from 1.0.1e) ... "darwin-i386-cc","cc:-arch i386 -O3 -fomit-frame-pointer -DL_ENDIAN::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:BN_LLONG RC4_INT RC4_CHUNK DES_UNROLL BF_PTR:".eval{my $asm=$x86_asm;$asm=~s/cast\-586\.o//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch i386 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", "debug-darwin-i386-cc","cc:-arch i386 -g3 -DL_ENDIAN::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:BN_LLONG RC4_INT RC4_CHUNK DES_UNROLL BF_PTR:${x86_asm}:macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch i386 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", "darwin64-x86_64-cc","cc:-arch x86_64 -O3 -DL_ENDIAN -Wall::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:SIXTY_FOUR_BIT_LONG RC4_CHAR RC4_CHUNK DES_INT DES_UNROLL:".eval{my $asm=$x86_64_asm;$asm=~s/rc4\-[^:]+//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch x86_64 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", ... There is a "debug-darwin64-x86_64-cc" entry in 'Configure' of 1.0.1c that is missing in 1.0.1e ##### MacOS X (a.k.a. Rhapsody or Darwin) setup (from 1.0.1c) ... "darwin-i386-cc","cc:-arch i386 -O3 -fomit-frame-pointer -DL_ENDIAN::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:BN_LLONG RC4_INT RC4_CHUNK DES_UNROLL BF_PTR:".eval{my $asm=$x86_asm;$asm=~s/cast\-586\.o//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch i386 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", "debug-darwin-i386-cc","cc:-arch i386 -g -DL_ENDIAN::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:BN_LLONG RC4_INT RC4_CHUNK DES_UNROLL BF_PTR:".eval{my $asm=$x86_asm;$asm=~s/cast\-586\.o//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch i386 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", "darwin64-x86_64-cc","cc:-arch x86_64 -O3 -fomit-frame-pointer -DL_ENDIAN -Wall::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:SIXTY_FOUR_BIT_LONG RC4_CHAR RC4_CHUNK DES_INT DES_UNROLL:".eval{my $asm=$x86_64_asm;$asm=~s/rc4\-[^:]+//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch x86_64 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", "debug-darwin64-x86_64-cc","cc:-arch x86_64 -g -DL_ENDIAN -Wall::-D_REENTRANT:MACOSX:-Wl,-search_paths_first%:SIXTY_FOUR_BIT_LONG RC4_CHAR RC4_CHUNK DES_INT DES_UNROLL:".eval{my $asm=$x86_64_asm;$asm=~s/rc4\-[^:]+//;$asm}.":macosx:dlfcn:darwin-shared:-fPIC -fno-common:-arch x86_64 -dynamiclib:.\$(SHLIB_MAJOR).\$(SHLIB_MINOR).dylib", ... Is this is mistake in Configure or is it intentional. If so, what is the reason? Thanks for the help. Alex