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

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