It looks like 32 bit builds set the -WX flag (treat warnings as errors) while the 64 bit builds don't.

        cl  -W3 -wd4090 -Gs0 -GF -Gy -nologo /MDd /Od -WX /Zi /Fdossl_static /I "." /I "crypto\include" /I "include" /I "crypto\ec\curve448\arch_32" /I "crypto\ec\curve448" -DDSO_WIN32 -DOPENSSL_SYS_WIN32 -DWIN32_LEAN_AND_MEAN -DL_ENDIAN -D_CRT_SECURE_NO_DEPRECATE -D_WINSOCK_DEPRECATED_NO_WARNINGS -DUNICODE -D_UNICODE -DDEBUG -D_DEBUG -DOPENSSL_USE_APPLINK -DOPENSSL_NO_STATIC_ENGINE -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_BN_ASM_PART_WORDS -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DRC4_ASM -DMD5_ASM -DRMD160_ASM -DAES_ASM -DVPAES_ASM -DWHIRLPOOL_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DPADLOCK_ASM -DPOLY1305_ASM "-DOPENSSLDIR=\"C:\\Program Files (x86)\\Common Files\\SSL\"" "-DENGINESDIR=\"C:\\checkouts\\install11\\lib\\engines-1_1\"" -c /Focrypto\ec\curve448\f_generic.obj @C:\cygwin64\tmp\nmA13D.tmp
f_generic.c
crypto\ec\curve448\f_generic.c(125) : error C2220: warning treated as error - no 'object' file generated crypto\ec\curve448\f_generic.c(125) : warning C4244: 'function' : conversion from 'dsword_t' to 'uint32_t', possible loss of data crypto\ec\curve448\f_generic.c(125) : warning C4244: 'function' : conversion from 'dsword_t' to 'uint32_t', possible loss of data crypto\ec\curve448\f_generic.c(138) : warning C4244: 'function' : conversion from 'dword_t' to 'uint32_t', possible loss of data NMAKE : fatal error U1077: '"C:\Program Files (x86)\Microsoft Visual Studio 10.0\VC\bin\cl.EXE"' : return code '0x2'
Stop.
NMAKE : fatal error U1077: '"C:\Program Files (x86)\Microsoft Visual Studio 10.0\VC\bin\nmake.exe"' : return code '0x2'
Stop.


perl configdata.pm --dump



Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114. Use of uninitialized value $prefix in concatenation (.) or string at configdata.pm line 15114.

Command line (with current working directory = .):

    C:\Perl64\bin\perl.exe Configure --prefix=C:\checkouts\install11 debug-VC-WIN32

Perl information:

    C:\Perl64\bin\perl.exe
    5.24.0 for MSWin32-x64-multi-thread

Enabled features:

    aria
    asm
    async
    autoalginit
    autoerrinit
    bf
    blake2
    camellia
    capieng
    cast
    chacha
    cmac
    cms
    comp
    ct
    deprecated
    des
    dgram
    dh
    dsa
    dso
    dtls
    dynamic-engine
    ec
    ec2m
    ecdh
    ecdsa
    engine
    err
    filenames
    gost
    hw(-.+)?
    idea
    makedepend
    md4
    mdc2
    multiblock
    nextprotoneg
    ocb
    ocsp
    pic
    poly1305
    posix-io
    psk
    rc2
    rc4
    rdrand
    rfc3779
    rmd160
    scrypt
    seed
    shared
    siphash
    sm3
    sm4
    sock
    srp
    srtp
    sse2
    ssl
    static-engine
    stdio
    tests
    threads
    tls
    ts
    ui-console
    whirlpool
    tls1
    tls1-method
    tls1_1
    tls1_1-method
    tls1_2
    tls1_2-method
    tls1_3
    dtls1
    dtls1-method
    dtls1_2
    dtls1_2-method

Disabled features:

    afalgeng                [not-linux]
    asan                    [default]   OPENSSL_NO_ASAN
    crypto-mdebug           [default] OPENSSL_NO_CRYPTO_MDEBUG
    crypto-mdebug-backtrace [default] OPENSSL_NO_CRYPTO_MDEBUG_BACKTRACE
    devcryptoeng            [default] OPENSSL_NO_DEVCRYPTOENG
    ec_nistp_64_gcc_128     [default] OPENSSL_NO_EC_NISTP_64_GCC_128
    egd                     [default]   OPENSSL_NO_EGD
    external-tests          [default] OPENSSL_NO_EXTERNAL_TESTS
    fuzz-libfuzzer          [default] OPENSSL_NO_FUZZ_LIBFUZZER
    fuzz-afl                [default]   OPENSSL_NO_FUZZ_AFL
    heartbeats              [default] OPENSSL_NO_HEARTBEATS
    md2                     [default]   OPENSSL_NO_MD2 (skip crypto\md2)
    msan                    [default]   OPENSSL_NO_MSAN
    rc5                     [default]   OPENSSL_NO_RC5 (skip crypto\rc5)
    sctp                    [default]   OPENSSL_NO_SCTP
    ssl-trace               [default] OPENSSL_NO_SSL_TRACE
    tls13downgrade          [default] OPENSSL_NO_TLS13DOWNGRADE
    ubsan                   [default]   OPENSSL_NO_UBSAN
    unit-test               [default] OPENSSL_NO_UNIT_TEST
    weak-ssl-ciphers        [default] OPENSSL_NO_WEAK_SSL_CIPHERS
    zlib                    [default]
    zlib-dynamic            [default]
    ssl3                    [default]   OPENSSL_NO_SSL3
    ssl3-method             [default] OPENSSL_NO_SSL3_METHOD

Config target attributes:

    aes_asm_src => "aes-586.s vpaes-x86.s aesni-x86.s",
    aes_obj => "aes-586.o vpaes-x86.o aesni-x86.o",
    apps_aux_src => "win32_init.c",
    apps_init_src => "../ms/applink.c",
    apps_obj => "win32_init.o",
    ar => "lib",
    arflags => "/nologo",
    aroutflag => "/out:",
    as => "nasm",
    asflags => "-f win32",
    asoutflag => "-o",
    bf_asm_src => "bf-586.s",
    bf_obj => "bf-586.o",
    bin_cflags => "/Zi /Fdapp /MDd",
    bin_lflags => "/subsystem:console /opt:ref",
    bn_asm_src => "bn-586.s co-586.s x86-mont.s x86-gf2m.s",
    bn_obj => "bn-586.o co-586.o x86-mont.o x86-gf2m.o",
    bn_ops => "BN_LLONG EXPORT_VAR_AS_FN",
    build_file => "makefile",
    build_scheme => [ "unified", "windows", "VC-W32" ],
    cast_asm_src => "c_enc.c",
    cast_obj => "c_enc.o",
    cc => "cl",
    cflags => "-W3 -wd4090 -Gs0 -GF -Gy -nologo /MDd /Od -WX",
    chacha_asm_src => "chacha-x86.s",
    chacha_obj => "chacha-x86.o",
    cmll_asm_src => "cmll-x86.s",
    cmll_obj => "cmll-x86.o",
    coutflag => "/Fo",
    cpp => "\$(CC) /EP /C",
    cppflags => "",
    cpuid_asm_src => "x86cpuid.s",
    cpuid_obj => "x86cpuid.o",
    defines => [ "DSO_WIN32", "OPENSSL_SYS_WIN32", "WIN32_LEAN_AND_MEAN", "L_ENDIAN", "_CRT_SECURE_NO_DEPRECATE", "_WINSOCK_DEPRECATED_NO_WARNINGS", "UNICODE", "_UNICODE", "DEBUG", "_DEBUG", "OPENSSL_USE_APPLINK", "OPENSSL_NO_STATIC_ENGINE", "OPENSSL_PIC", "OPENSSL_CPUID_OBJ", "OPENSSL_BN_ASM_PART_WORDS", "OPENSSL_IA32_SSE2", "OPENSSL_BN_ASM_MONT", "OPENSSL_BN_ASM_GF2m", "SHA1_ASM", "SHA256_ASM", "SHA512_ASM", "RC4_ASM", "MD5_ASM", "RMD160_ASM", "AES_ASM", "VPAES_ASM", "WHIRLPOOL_ASM", "GHASH_ASM", "ECP_NISTZ256_ASM", "PADLOCK_ASM", "POLY1305_ASM" ],
    des_asm_src => "des-586.s crypt586.s",
    des_obj => "des-586.o crypt586.o",
    disable => [  ],
    dso_cflags => "/Zi /Fddso",
    dso_cxxflags => "",
    dso_extension => "",
    dso_lflags => "/dll",
    dso_scheme => "WIN32",
    ec_asm_src => "ecp_nistz256.c ecp_nistz256-x86.s",
    ec_obj => "ecp_nistz256.o ecp_nistz256-x86.o",
    enable => [  ],
    ex_libs => "ws2_32.lib gdi32.lib advapi32.lib crypt32.lib user32.lib",
    exe_extension => "",
    hashbangperl => "/usr/bin/env perl",
    includes => [  ],
    ld => "link",
    lflags => "/nologo /debug",
    lib_cflags => "/Zi /Fdossl_static",
    loutflag => "/out:",
    md5_asm_src => "md5-586.s",
    md5_obj => "md5-586.o",
    modes_asm_src => "ghash-x86.s",
    modes_obj => "ghash-x86.o",
    mt => "mt",
    mtflags => "-nologo",
    mtinflag => "-manifest ",
    mtoutflag => "-outputresource:",
    padlock_asm_src => "e_padlock-x86.s",
    padlock_obj => "e_padlock-x86.o",
    perlasm_scheme => "win32n",
    poly1305_asm_src => "poly1305-x86.s",
    poly1305_obj => "poly1305-x86.o",
    ranlib => "CODE(0x48e7f0)",
    rc => "rc",
    rc4_asm_src => "rc4-586.s",
    rc4_obj => "rc4-586.o",
    rc5_asm_src => "rc5-586.s",
    rc5_obj => "rc5-586.o",
    rcoutflag => "/fo",
    rmd160_asm_src => "rmd-586.s",
    rmd160_obj => "rmd-586.o",
    sha1_asm_src => "sha1-586.s sha256-586.s sha512-586.s",
    sha1_obj => "sha1-586.o sha256-586.o sha512-586.o",
    shared_cflag => "",
    shared_defines => [  ],
    shared_extension => "",
    shared_extension_simple => "",
    shared_ldflag => "/dll",
    shared_rcflag => "",
    shared_target => "win-shared",
   sys_id => "WIN32",
    thread_defines => [  ],
    thread_scheme => "winthreads",
    unistd => "<unistd.h>",
    uplink_aux_src => "../ms/uplink.c",
    uplink_obj => "../ms/uplink.o",
    wp_asm_src => "wp_block.c wp-mmx.s",
    wp_obj => "wp_block.o wp-mmx.o",

Recorded environment:

    AR =
    ARFLAGS =
    AS =
    ASFLAGS =
    BUILDFILE =
    CC = cl
    CFLAGS =
    CPP =
    CPPDEFINES =
    CPPFLAGS =
    CPPINCLUDES =
    CROSS_COMPILE =
    CXX =
    CXXFLAGS =
    HASHBANGPERL =
    LD = link
    LDFLAGS =
    LDLIBS =
    MT =
    MTFLAGS =
    OPENSSL_LOCAL_CONFIG_DIR =
    PERL = perl
    RANLIB =
    RC =
    RCFLAGS =
    RM =
    WINDRES =

Makevars:

    AR              = lib
    ARFLAGS         = /nologo
    AS              = nasm
    ASFLAGS         = -f win32
    CC              = cl
    CFLAGS          = -W3 -wd4090 -Gs0 -GF -Gy -nologo /MDd /Od -WX
    CPP             = $(CC) /EP /C
    CPPDEFINES      = DSO_WIN32 OPENSSL_SYS_WIN32 WIN32_LEAN_AND_MEAN L_ENDIAN _CRT_SECURE_NO_DEPRECATE _WINSOCK_DEPRECATED_NO_WARNINGS UNICODE _UNICODE DEBUG _DEBUG OPENSSL_USE_APPLINK OPENSSL_NO_STATIC_ENGINE OPENSSL_PIC OPENSSL_CPUID_OBJ OPENSSL_BN_ASM_PART_WORDS OPENSSL_IA32_SSE2 OPENSSL_BN_ASM_MONT OPENSSL_BN_ASM_GF2m SHA1_ASM SHA256_ASM SHA512_ASM RC4_ASM MD5_ASM RMD160_ASM AES_ASM VPAES_ASM WHIRLPOOL_ASM GHASH_ASM ECP_NISTZ256_ASM PADLOCK_ASM POLY1305_ASM
    CPPFLAGS        =
    CPPINCLUDES     =
   CXXFLAGS        =
    HASHBANGPERL    = perl
    LD              = link
    LDFLAGS         = /nologo /debug
    LDLIBS          = ws2_32.lib gdi32.lib advapi32.lib crypt32.lib user32.lib
    MT              = mt
    MTFLAGS         = -nologo
    RANLIB          = ranlib
    RC              = rc

NOTE: These variables only represent the configuration view.  The build file
template may have processed these variables further, please have a look at the
build file for more exact data:
    makefile

build file:

    makefile

build file templates:

    Configurations\windows-makefile.tmpl
    Configurations\common.tmpl

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