Installation fails when calling make install to a Windows system directory (clang, Mingw, Windows 10 Home)

I am attempting to set the installation directory to C:\Windows\System32\OpenSSL The two DLLs are generated successfully in the requested system directory, however the script fails before the EXE is created.

Here is the error when running make install_sw:

...
install ./include/openssl/x509.h -> C:/Windows/System32/OpenSSL/include/openssl/x509.h
install ./include/openssl/x509_vfy.h -> C:/Windows/System32/OpenSSL/include/openssl/x509_vfy.h
install ./include/openssl/x509err.h -> C:/Windows/System32/OpenSSL/include/openssl/x509err.h
install ./include/openssl/x509v3.h -> C:/Windows/System32/OpenSSL/include/openssl/x509v3.h
install ./include/openssl/x509v3err.h -> C:/Windows/System32/OpenSSL/include/openssl/x509v3err.h
install libcrypto.a -> C:/Windows/System32/OpenSSL/lib/libcrypto.a
C:\msys64\mingw32\bin\ranlib.exe: 'C:/Windows/System32/OpenSSL/lib/libcrypto.a.new': No such file
make: *** [Makefile:2985: install_dev] Error 1

However, I can see the libcrypto.a.new file in that directory.

I created a "patched" configure file that allowed me to pass in a full Windows path:

sed \
   -e 's/die "Directory given with --prefix/print "Directory given with --prefix/g' \
   -e 's/"aria",$/"apps", "aria",/g' \
   < ./Configure > ./Configure-patched
chmod a+x ./Configure-patched

$ perl configdata.pm --dump

Command line (with current working directory = .):

    perl ./Configure mingw -Wno-unused-command-line-argument no-tests no-unit-test -fno-ident -Wa,--noexecstack -Qunused-arguments --target=x86_64-w64-mingw32 --release no-dso no-loadereng no-padlockeng no-ssl-trace no-filenames no-module --prefix=C:/Windows/System32/OpenSSL --openssldir=ssl --libdir=lib

Perl information:

    perl
    5.36.0 for x86_64-msys-thread-multi

Enabled features:

    apps
    aria
    asm
    async
    autoalginit
    autoerrinit
    autoload-config
    bf
    blake2
    bulk
    cached-fetch
    camellia
    capieng
    cast
    chacha
    cmac
    cmp
    cms
    comp
    ct
    deprecated
    des
    dgram
    dh
    dsa
    dtls
    ec
    ec2m
    ecdh
    ecdsa
    engine
    err
    gost
    idea
    legacy
    makedepend
    md4
    mdc2
    multiblock
    nextprotoneg
    ocb
    ocsp
    pic
    pinshared
    poly1305
    posix-io
    psk
    rc2
    rc4
    rdrand
    rfc3779
    rmd160
    scrypt
    secure-memory
    seed
    shared
    siphash
    siv
    sm2
    sm3
    sm4
    sock
    srp
    srtp
    sse2
    ssl
    static-engine
    stdio
    threads
    tls
    ts
    ui-console
    uplink
    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:

    acvp-tests          [cascade]   OPENSSL_NO_ACVP_TESTS
    afalgeng            [not-linux] OPENSSL_NO_AFALGENG
    asan                [default]   OPENSSL_NO_ASAN
    buildtest-c++       [default]
    crypto-mdebug       [default]   OPENSSL_NO_CRYPTO_MDEBUG
    devcryptoeng        [default]   OPENSSL_NO_DEVCRYPTOENG
    dso                 [option]    OPENSSL_NO_DSO
    dynamic-engine      [cascade]
    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
    filenames           [option]    OPENSSL_NO_FILENAMES
    fips                [default]
    fips-securitychecks [cascade]   OPENSSL_NO_FIPS_SECURITYCHECKS
    fuzz-afl            [default]   OPENSSL_NO_FUZZ_AFL
    fuzz-libfuzzer      [default]   OPENSSL_NO_FUZZ_LIBFUZZER
    ktls                [default]   OPENSSL_NO_KTLS
    loadereng           [option]    OPENSSL_NO_LOADERENG
    md2                 [default]   OPENSSL_NO_MD2 (skip crypto/md2)
    module              [option]
    msan                [default]   OPENSSL_NO_MSAN
    padlockeng          [option]    OPENSSL_NO_PADLOCKENG
    rc5                 [default]   OPENSSL_NO_RC5 (skip crypto/rc5)
    sctp                [default]   OPENSSL_NO_SCTP
    ssl-trace           [option]    OPENSSL_NO_SSL_TRACE
    tests               [option]    OPENSSL_NO_TESTS
    trace               [default]   OPENSSL_NO_TRACE
    ubsan               [default]   OPENSSL_NO_UBSAN
    unit-test           [option]    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:

    AR => "ar",
    ARFLAGS => "qc",
    CC => "gcc",
    CFLAGS => "-Wall -O3 -fomit-frame-pointer",
    HASHBANGPERL => "/usr/bin/env perl",
    RANLIB => "ranlib",
    RC => "windres",
    asm_arch => "x86",
    bn_ops => "BN_LLONG",
    build_file => "Makefile",
    build_scheme => [ "unified", "unix" ],
    cflags => "-m32",
    cppflags => "-DUNICODE -D_UNICODE -DWIN32_LEAN_AND_MEAN -D_MT",
    defines => [ "OPENSSL_BUILDING_OPENSSL" ],
    disable => [  ],
    dso_scheme => "win32",
    enable => [  ],
    ex_libs => "-lws2_32 -lgdi32 -lcrypt32",
    includes => [  ],
    lflags => "",
    lib_cflags => "",
    lib_cppflags => "-DL_ENDIAN",
    lib_defines => [  ],
    module_cflags => "",
    module_cxxflags => undef,
    module_ldflags => "-static-libgcc -shared -Wl,--enable-auto-image-base",
    multilib => "",
    perl_platform => "mingw",
    perlasm_scheme => "coff",
    shared_argfileflag => "\@",
    shared_cflag => "",
    shared_cppflags => "_WINDLL",
    shared_defflag => "",
    shared_defines => [  ],
    shared_impflag => "-Wl,--out-implib=",
    shared_ldflag => "-static-libgcc -shared -Wl,--enable-auto-image-base",
    shared_rcflag => "--target=pe-i386",
    shared_target => "mingw-shared",
    sys_id => "MINGW32",
    thread_defines => [  ],
    thread_scheme => "winthreads",
    unistd => "<unistd.h>",
    uplink_arch => "x86",

Recorded environment:

    AR =
    BUILDFILE =
    CC = clang
    CFLAGS =
    CPPFLAGS =
    CROSS_COMPILE =
    CXX =
    CXXFLAGS =
    HASHBANGPERL =
    LDFLAGS =
    LDLIBS =
    OPENSSL_LOCAL_CONFIG_DIR =
    PERL =
    RANLIB =
    RC =
    RCFLAGS =
    WINDRES =
    __CNF_CFLAGS =
    __CNF_CPPDEFINES =
    __CNF_CPPFLAGS =
    __CNF_CPPINCLUDES =
    __CNF_CXXFLAGS =
    __CNF_LDFLAGS =
    __CNF_LDLIBS =

Makevars:

    AR              = ar
    ARFLAGS         = qc
    CC              = clang
    CFLAGS          = -Wall -O3 -fomit-frame-pointer -Wno-unused-command-line-argument -fno-ident -Wa,--noexecstack -Qunused-arguments --target=x86_64-w64-mingw32
    CPPDEFINES      =
    CPPFLAGS        =
    CPPINCLUDES     =
    CXXFLAGS        = -Wno-unused-command-line-argument -fno-ident -Wa,--noexecstack -Qunused-arguments --target=x86_64-w64-mingw32
    HASHBANGPERL    = /usr/bin/env perl
    LDFLAGS         =
    LDLIBS          =
    PERL            = perl
    RANLIB          = ranlib
    RC              = windres
    RCFLAGS         =

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/common0.tmpl
    Configurations/unix-Makefile.tmpl

make clean; make build_sw

make install_sw