Unable to install ruby 3.1.4 on M1 macOS 14.3.1 on arm64 using ruby-build 20240119

[valdrinkuchi]

Using rbenv I was able to install ruby version before. I just realized that something is wrong while I was trying to install ruby version 3.1.4

System information

which brew    
=> brew: aliased to arch -arm64 /opt/homebrew/bin/brew

which rbenv
=> which rbenv     
rbenv () {
        local command
        command="${1:-}" 
        if [ "$#" -gt 0 ]
        then
                shift
        fi
        case "$command" in
                (rehash | shell) eval "$(rbenv "sh-$command" "$@")" ;;
                (*) command rbenv "$command" "$@" ;;
        esac
}

which ruby
=> /Users/valdrinkuchi/.rbenv/shims/ruby

rbenv versions
=> system
  2.7.2
  2.7.4
  3.0.3
  3.2.2

rbenv install 3.1.4
=> cd /var/folders/my/tjvgd1591sv3q08h635pzfs80000gn/T/ruby-build.20240220085326.40640.cuBsTm
==> Downloading ruby-3.1.4.tar.gz...
-> curl -q -fL -o ruby-3.1.4.tar.gz https://cache.ruby-lang.org/pub/ruby/3.1/ruby-3.1.4.tar.gz
-> tar xzf ruby-3.1.4.tar.gz
cd /var/folders/my/tjvgd1591sv3q08h635pzfs80000gn/T/ruby-build.20240220085326.40640.cuBsTm/ruby-3.1.4
==> Installing ruby-3.1.4...
-> ./configure "--prefix=$HOME/.rbenv/versions/3.1.4" --enable-shared --with-readline-dir=/usr/local/opt/readline --with-libyaml-dir=/usr/local/opt/libyaml --with-gmp-dir=/usr/local/opt/gmp --with-ext=openssl,psych,+ --with-openssl-dir=/opt/homebrew/opt/openssl@3

...

Configuration summary for ruby version 3.1.4

   * Installation prefix: /Users/valdrinkuchi/.rbenv/versions/3.1.4
   * exec prefix:         ${prefix}
   * arch:                arm64-darwin23
   * site arch:           ${arch}
   * RUBY_BASE_NAME:      ruby
   * enable shared:       yes
   * ruby lib prefix:     ${libdir}/${RUBY_BASE_NAME}
   * site libraries path: ${rubylibprefix}/${sitearch}
   * vendor path:         ${rubylibprefix}/vendor_ruby
   * target OS:           darwin23
   * compiler:            clang
   * with pthread:        yes
   * with coroutine:      arm64
   * enable shared libs:  yes
   * dynamic library ext: bundle
   * CFLAGS:              -fdeclspec ${optflags} ${debugflags} ${warnflags}
   * LDFLAGS:             -L. -fstack-protector-strong \
                          -L/usr/local/opt/gmp/lib -L/usr/local/lib
   * DLDFLAGS:            -L/usr/local/opt/gmp/lib \
                          -Wl,-undefined,dynamic_lookup
   * optflags:            -O3 -fno-fast-math
   * debugflags:          -ggdb3
   * warnflags:           -Wall -Wextra -Wdeprecated-declarations \
                          -Wdivision-by-zero \
                          -Wimplicit-function-declaration -Wimplicit-int \
                          -Wmisleading-indentation -Wpointer-arith \
                          -Wshorten-64-to-32 -Wwrite-strings \
                          -Wold-style-definition -Wmissing-noreturn \
                          -Wno-cast-function-type \
                          -Wno-constant-logical-operand -Wno-long-long \
                          -Wno-missing-field-initializers \
                          -Wno-overlength-strings -Wno-parentheses-equality \
                          -Wno-self-assign -Wno-tautological-compare \
                          -Wno-unused-parameter -Wno-unused-value \
                          -Wunused-variable -Wextra-tokens -Wundef
   * strip command:       strip -A -n
   * install doc:         rdoc
   * JIT support:         yes
   * man page type:       doc
   * BASERUBY -v:         ruby 3.0.3p157 (2021-11-24 revision 3fb7d2cadc) \
                          [arm64-darwin23]

---
-> make -j 10
	BASERUBY = /Users/valdrinkuchi/.rbenv/shims/ruby --disable=gems
	CC = clang
	LD = clang
	LDSHARED = clang -dynamiclib
	CFLAGS = -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef -std=gnu99  -fno-common -pipe 
	XCFLAGS = -D_FORTIFY_SOURCE=2 -fstack-protector-strong -fno-strict-overflow -fvisibility=hidden -DRUBY_EXPORT -I. -I.ext/include/arm64-darwin23 -I./include -I. -I./enc/unicode/13.0.0
	CPPFLAGS = -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   
	DLDFLAGS = -L/usr/local/opt/gmp/lib -Wl,-undefined,dynamic_lookup -install_name /Users/valdrinkuchi/.rbenv/versions/3.1.4/lib/libruby.3.1.dylib -compatibility_version 3.1 -current_version 3.1.4  -fstack-protector-strong -framework CoreFoundation  -fstack-protector-strong -framework CoreFoundation  
	SOLIBS = -lpthread -ldl -lobjc
	LANG = en_US.UTF-8
	LC_ALL = 
	LC_CTYPE = UTF-8
	MFLAGS = - --jobserver-fds=6,7 -j
Apple clang version 15.0.0 (clang-1500.1.0.2.5)
Target: arm64-apple-darwin23.3.0

...


/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:419:9: warning: 'EC_KEY_get0_private_key' is deprecated [-Wdeprecated-declarations]
    if (EC_KEY_get0_private_key(ec))
        ^
/opt/homebrew/opt/openssl@3/include/openssl/ec.h:1067:1: note: 'EC_KEY_get0_private_key' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 const BIGNUM *EC_KEY_get0_private_key(const EC_KEY *key);
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:436:5: warning: 'EVP_PKEY_get0_EC_KEY' is deprecated [-Wdeprecated-declarations]
    GetEC(self, ec);
    ^
ossl_pkey_ec.c:24:13: note: expanded from macro 'GetEC'
    (key) = EVP_PKEY_get0_EC_KEY(_pkey); \
            ^
/opt/homebrew/opt/openssl@3/include/openssl/evp.h:1379:1: note: 'EVP_PKEY_get0_EC_KEY' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:436:5: warning: assigning to 'EC_KEY *' (aka 'struct ec_key_st *') from 'const struct ec_key_st *' discards qualifiers [-Wincompatible-pointer-types-discards-qualifiers]
    GetEC(self, ec);
    ^~~~~~~~~~~~~~~
ossl_pkey_ec.c:24:11: note: expanded from macro 'GetEC'
    (key) = EVP_PKEY_get0_EC_KEY(_pkey); \
          ^ ~~~~~~~~~~~~~~~~~~~~~~~~~~~
ossl_pkey_ec.c:437:9: warning: 'EC_KEY_get0_public_key' is deprecated [-Wdeprecated-declarations]
    if (EC_KEY_get0_public_key(ec) == NULL)
        ^
/opt/homebrew/opt/openssl@3/include/openssl/ec.h:1081:1: note: 'EC_KEY_get0_public_key' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 const EC_POINT *EC_KEY_get0_public_key(const EC_KEY *key);
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:439:9: warning: 'EC_KEY_get0_private_key' is deprecated [-Wdeprecated-declarations]
    if (EC_KEY_get0_private_key(ec))
        ^
/opt/homebrew/opt/openssl@3/include/openssl/ec.h:1067:1: note: 'EC_KEY_get0_private_key' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 const BIGNUM *EC_KEY_get0_private_key(const EC_KEY *key);
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:577:21: warning: 'PEM_read_bio_ECPKParameters' is deprecated [-Wdeprecated-declarations]
            group = PEM_read_bio_ECPKParameters(in, NULL, NULL, NULL);
                    ^
/opt/homebrew/opt/openssl@3/include/openssl/pem.h:465:21: note: 'PEM_read_bio_ECPKParameters' has been explicitly marked deprecated here
DECLARE_PEM_rw_attr(OSSL_DEPRECATEDIN_3_0, ECPKParameters, EC_GROUP)
                    ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:1023:13: warning: 'PEM_write_bio_ECPKParameters' is deprecated [-Wdeprecated-declarations]
        i = PEM_write_bio_ECPKParameters(out, group);
            ^
/opt/homebrew/opt/openssl@3/include/openssl/pem.h:465:21: note: 'PEM_write_bio_ECPKParameters' has been explicitly marked deprecated here
DECLARE_PEM_rw_attr(OSSL_DEPRECATEDIN_3_0, ECPKParameters, EC_GROUP)
                    ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:1081:10: warning: 'ECPKParameters_print' is deprecated [-Wdeprecated-declarations]
    if (!ECPKParameters_print(out, group, 0)) {
         ^
/opt/homebrew/opt/openssl@3/include/openssl/ec.h:945:1: note: 'ECPKParameters_print' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 int ECPKParameters_print(BIO *bp, const EC_GROUP *x,
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_pkey_ec.c:1168:14: warning: 'EC_POINT_bn2point' is deprecated [-Wdeprecated-declarations]
            point = EC_POINT_bn2point(group, GetBNPtr(arg2), NULL, ossl_bn_ctx);
                    ^
/opt/homebrew/opt/openssl@3/include/openssl/ec.h:793:1: note: 'EC_POINT_bn2point' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 EC_POINT *EC_POINT_bn2point(const EC_GROUP *,
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
compiling ossl_ssl_session.c
compiling ossl_ts.c
1 warning generated.
44 warnings generated.
compiling ossl_x509.c
compiling ossl_x509attr.c
40 warnings generated.
ossl_ssl.c:294:12: warning: 'EVP_PKEY_get0_DH' is deprecated [-Wdeprecated-declarations]
    return EVP_PKEY_get0_DH(pkey);
           ^
/opt/homebrew/opt/openssl@3/include/openssl/evp.h:1371:1: note: 'EVP_PKEY_get0_DH' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0 const struct dh_st *EVP_PKEY_get0_DH(const EVP_PKEY *pkey);
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_ssl.c:294:12: warning: returning 'const struct dh_st *' from a function with result type 'DH *' (aka 'struct dh_st *') discards qualifiers [-Wincompatible-pointer-types-discards-qualifiers]
    return EVP_PKEY_get0_DH(pkey);
           ^~~~~~~~~~~~~~~~~~~~~~
ossl_ssl.c:769:5: warning: 'SSL_CTX_set_tmp_dh_callback' is deprecated [-Wdeprecated-declarations]
    SSL_CTX_set_tmp_dh_callback(ctx, ossl_tmp_dh_callback);
    ^
/opt/homebrew/opt/openssl@3/include/openssl/ssl.h:2263:1: note: 'SSL_CTX_set_tmp_dh_callback' has been explicitly marked deprecated here
OSSL_DEPRECATEDIN_3_0
^
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:194:49: note: expanded from macro 'OSSL_DEPRECATEDIN_3_0'
#   define OSSL_DEPRECATEDIN_3_0                OSSL_DEPRECATED(3.0)
                                                ^
compiling ossl_x509cert.c
/opt/homebrew/opt/openssl@3/include/openssl/macros.h:62:52: note: expanded from macro 'OSSL_DEPRECATED'
#     define OSSL_DEPRECATED(since) __attribute__((deprecated))
                                                   ^
ossl_ssl.c:1643:12: warning: passing arguments to a function without a prototype is deprecated in all versions of C and is not supported in C2x [-Wdeprecated-non-prototype]
        ret = func(ssl);
                  ^
compiling ossl_x509crl.c
compiling ossl_x509ext.c
compiling ossl_x509name.c
compiling ossl_x509req.c
compiling ossl_x509revoked.c
compiling ossl_x509store.c
4 warnings generated.
installing default openssl libraries
linking shared-object openssl.bundle
linking shared-object psych.bundle
ld: warning: ignoring duplicate libraries: '-lruby.3.1'
ld: warning: ignoring duplicate libraries: '-lruby.3.1'
1 warning generated.
linking shared-object ripper.bundle
ld: warning: ignoring duplicate libraries: '-lruby.3.1'
make: *** [build-ext] Error 2
external command failed with status 2

I would appreciate any help.

[mislav]

Hi, thanks for providing detailed output. From what you've shared, I see no visible error message anywhere. Most of the log you've pasted is "warning" and "note" lines, which are non-fatal and can be safely ignored. However, building suddenly fails with a make: *** [build-ext] Error 2 line. I don't understand what failed, but perhaps it was while building an extension, for example the "openssl" extension?

You could cd into a temporary build directory that ruby-build uses when compiling 3.1.4 and look for the ext/openssl/mkmf.log. There could be additional error messages there. Or, in some of the other mkmf.log files?

Please check your log files again and search for "error" or "fatal" to better isolate the lines that actually report a fatal error.

[valdrinkuchi]

Thanks a lot for looking into it. Here is the output of the ext/openssl/mkmf.log

=== OpenSSL for Ruby configurator ===
have_func: checking for rb_io_maybe_wait()... -------------------- yes

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc   "
checked program was:
/* begin */
1: #include "ruby.h"
2: 
3: int main(int argc, char **argv)
4: {
5:   return !!argv[argc];
6: }
/* end */

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc   "
conftest.c:14:57: error: use of undeclared identifier 'rb_io_maybe_wait'
int t(void) { void ((*volatile p)()); p = (void ((*)()))rb_io_maybe_wait; return !p; }
                                                        ^
1 error generated.
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: int t(void) { void ((*volatile p)()); p = (void ((*)()))rb_io_maybe_wait; return !p; }
/* end */

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc   "
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: extern void rb_io_maybe_wait();
15: int t(void) { rb_io_maybe_wait(); return 0; }
/* end */

--------------------

=== Checking for system dependent stuff... ===
have_library: checking for t_open() in -lnsl... -------------------- no

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lnsl   "
conftest.c:14:57: error: use of undeclared identifier 't_open'
int t(void) { void ((*volatile p)()); p = (void ((*)()))t_open; return !p; }
                                                        ^
1 error generated.
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: int t(void) { void ((*volatile p)()); p = (void ((*)()))t_open; return !p; }
/* end */

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lnsl   "
ld: library 'nsl' not found
clang: error: linker command failed with exit code 1 (use -v to see invocation)
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: extern void t_open();
15: int t(void) { t_open(); return 0; }
/* end */

--------------------

have_library: checking for socket() in -lsocket... -------------------- no

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lsocket   "
conftest.c:14:57: error: use of undeclared identifier 'socket'
int t(void) { void ((*volatile p)()); p = (void ((*)()))socket; return !p; }
                                                        ^
1 error generated.
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: int t(void) { void ((*volatile p)()); p = (void ((*)()))socket; return !p; }
/* end */

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lsocket   "
ld: library 'socket' not found
clang: error: linker command failed with exit code 1 (use -v to see invocation)
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: extern void socket();
15: int t(void) { socket(); return 0; }
/* end */

--------------------

=== Checking for required stuff... ===
have_header: checking for openssl/ssl.h... -------------------- yes

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe   -c conftest.c"
checked program was:
/* begin */
1: #include "ruby.h"
2: 
3: #include <openssl/ssl.h>
/* end */

--------------------

have_library: checking for CRYPTO_malloc() in -lcrypto... -------------------- no

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lcrypto   "
conftest.c:14:57: error: use of undeclared identifier 'CRYPTO_malloc'
int t(void) { void ((*volatile p)()); p = (void ((*)()))CRYPTO_malloc; return !p; }
                                                        ^
1 error generated.
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: int t(void) { void ((*volatile p)()); p = (void ((*)()))CRYPTO_malloc; return !p; }
/* end */

DYLD_FALLBACK_LIBRARY_PATH=.:../.. "clang -o conftest -I../../.ext/include/arm64-darwin23 -I../.././include -I../.././ext/openssl -I/usr/local/opt/openssl@3/include -I/usr/local/opt/gmp/include -D_XOPEN_SOURCE -D_DARWIN_C_SOURCE -D_DARWIN_UNLIMITED_SELECT -D_REENTRANT   -fdeclspec -O3 -fno-fast-math -ggdb3 -Wall -Wextra -Wdeprecated-declarations -Wdivision-by-zero -Wimplicit-function-declaration -Wimplicit-int -Wmisleading-indentation -Wpointer-arith -Wshorten-64-to-32 -Wwrite-strings -Wold-style-definition -Wmissing-noreturn -Wno-cast-function-type -Wno-constant-logical-operand -Wno-long-long -Wno-missing-field-initializers -Wno-overlength-strings -Wno-parentheses-equality -Wno-self-assign -Wno-tautological-compare -Wno-unused-parameter -Wno-unused-value -Wunused-variable -Wextra-tokens -Wundef  -fno-common -pipe conftest.c  -L. -L../.. -L/usr/local/opt/openssl@3/lib -L. -fstack-protector-strong -L/usr/local/opt/gmp/lib -L/usr/local/lib     -lruby.3.1-static -framework CoreFoundation -lpthread -ldl -lobjc -lcrypto   "
ld: warning: ignoring file '/usr/local/Cellar/openssl@3/3.2.0_1/lib/libcrypto.3.dylib': found architecture 'x86_64', required architecture 'arm64'
ld: Undefined symbols:
  _CRYPTO_malloc, referenced from:
      _t in conftest-1337d2.o
clang: error: linker command failed with exit code 1 (use -v to see invocation)
checked program was:
/* begin */
 1: #include "ruby.h"
 2: 
 3: /*top*/
 4: extern int t(void);
 5: int main(int argc, char **argv)
 6: {
 7:   if (argc > 1000000) {
 8:     int (* volatile tp)(void)=(int (*)(void))&t;
 9:     printf("%d", (*tp)());
10:   }
11: 
12:   return !!argv[argc];
13: }
14: extern void CRYPTO_malloc();
15: int t(void) { CRYPTO_malloc(); return 0; }
/* end */

--------------------

=== Checking for required stuff failed. ===
Makefile wasn't created. Fix the errors above.
/private/var/folders/my/tjvgd1591sv3q08h635pzfs80000gn/T/ruby-build.20240221155319.59639.kEtr19/ruby-3.1.4/ext/openssl/extconf.rb:100: OpenSSL library could not be found. You might want to use --with-openssl-dir=<dir> option to specify the prefix where OpenSSL is installed.
	/private/var/folders/my/tjvgd1591sv3q08h635pzfs80000gn/T/ruby-build.20240221155319.59639.kEtr19/ruby-3.1.4/ext/openssl/extconf.rb:100:in `<top (required)>'
	./ext/extmk.rb:223:in `load'
	./ext/extmk.rb:223:in `block in extmake'
	/private/var/folders/my/tjvgd1591sv3q08h635pzfs80000gn/T/ruby-build.20240221155319.59639.kEtr19/ruby-3.1.4/lib/mkmf.rb:324:in `open'
	./ext/extmk.rb:219:in `extmake'
	./ext/extmk.rb:635:in `block in <main>'
	./ext/extmk.rb:631:in `each'
	./ext/extmk.rb:631:in `<main>'

[mislav]

I think the culprit is this line:

ld: warning: ignoring file '/usr/local/Cellar/openssl@3/3.2.0_1/lib/libcrypto.3.dylib': found architecture 'x86_64', required architecture 'arm64'

Is it possible that you've installed openssl@3 for x86_64 architecture instead for your computer's arm64 architecture, perhaps by doing arch -x86_64 /opt/homebrew/bin/brew install openssl@3?

You could try reinstalling openssl@3 and trying again. Note that you shouldn't be doing any arch tricks to do that.