Can't use truffleruby 23.1.0 on MacOS with XCode 15

[HoneyryderChuck]

I've installed truffleruby 23.1.0 using homebrew. All went well, until I use openssl:

> ruby -e "require 'openssl'"


<internal:core> core/kernel.rb:260:in `require': you may need to install the system OpenSSL library libssl - see https://github.com/oracle/truffleruby/blob/master/doc/user/installing-libssl.md (dlopen(/user/.rubies/truffleruby-23.1.0/lib/mri/openssl.bundle, 0x0002): Library not loaded: @rpath/libgraalvm-llvm.1.dylib (RuntimeError)
  Referenced from: <D3AD165B-0AC8-3019-836C-9D3781CEDAA8> /user/.rubies/truffleruby-23.1.0/lib/mri/openssl.bundle
  Reason: tried: '/usr/local/opt/openssl@3/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@3/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/opt/openssl@3/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@3/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/lib/libgraalvm-llvm.1.dylib' (no such file, not in dyld cache))
        from /user/.rubies/truffleruby-23.1.0/lib/mri/openssl.rb:13:in `<top (required)>'
        from <internal:core> core/kernel.rb:260:in `require'
        from -e:1:in `<main>'

It seems that truffleruby 23 requires the installation of the graalvm, where previous ones didn't? If so, shouldn't it be declared as a dependency in the formula, and installed accordingly? Or is this smth else? (I've used OPENSSL_PREFIX against locally installed openssl@3 and @1.1).

[eregon]

I am not aware of any truffleruby Homebrew formula, could you point me to it?
i.e. there is no truffleruby.rb at https://github.com/Homebrew/homebrew-core/tree/master/Formula/t

It sounds like whatever tool installed truffleruby did not run the post install hook but that's necessary.
Although the error message is weird, it sounds like it's trying to load openssl.bundle natively and not with Sulong or so.

libgraalvm-llvm.1.dylib is provided in the truffleruby standalone, there is no need to install GraalVM.

The README has details for various supported ways to install TruffleRuby.

[HoneyryderChuck]

I see, so you're saying this may be a ruby-install issue? Will cross-post.

[eregon]

Ah you used ruby-install, I thought from the description you used Homebrew directly to install truffleruby.
ruby-install should work, we'll try to reproduce.

[eregon]

I cannot reproduce this on Linux.
@andrykonchin Could you try to repro this on darwin-amd64 with ruby-install truffleruby -r ~/tmp? (using ruby-install 0.9.2 or master)

[eregon]

@HoneyryderChuck To help us investigate, could you:

rm -rf /user/.rubies/truffleruby-23.1.0
ruby-install truffleruby

And post the full output here?

[andrykonchin]

I cannot reproduce the issue on macOS (i9):

$ ruby-install -V
ruby-install: 0.9.2

$ ruby-install truffleruby -r ~/tmp
>>> Updating truffleruby versions ...
>>> Installing truffleruby 23.1.0 into /Users/andrykonchin/tmp/truffleruby-23.1.0 ...
>>> Installing dependencies for truffleruby 23.1.0 ...
Warning: openssl@1.1 1.1.1v is already installed and up-to-date.
To reinstall 1.1.1v, run:
  brew reinstall openssl@1.1
Warning: libyaml 0.2.5 is already installed and up-to-date.
To reinstall 0.2.5, run:
  brew reinstall libyaml
>>> Downloading https://github.com/oracle/truffleruby/releases/download/graal-23.1.0/truffleruby-23.1.0-macos-amd64.tar.gz into /Users/andrykonchin/src ...
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
  0     0    0     0    0     0      0      0 --:--:-- --:--:-- --:--:--     0
100  215M  100  215M    0     0  8929k      0  0:00:24  0:00:24 --:--:-- 9265k
>>> Verifying truffleruby-23.1.0-macos-amd64.tar.gz ...
>>> Extracting truffleruby-23.1.0-macos-amd64.tar.gz to /Users/andrykonchin/src/truffleruby-23.1.0-macos-amd64 ...
>>> Installing truffleruby 23.1.0 ...
>>> Running truffleruby post-install hook ...
Recompiling the OpenSSL C extension (against the installed libssl)
checking for rb_io_maybe_wait(0, Qnil, Qnil, Qnil) in ruby/io.h... yes
checking for t_open() in -lnsl... no
checking for socket() in -lsocket... no
checking for openssl/ssl.h... yes
checking for CRYPTO_malloc() in -lcrypto... yes
checking for SSL_new() in -lssl... yes
checking for LIBRESSL_VERSION_NUMBER in openssl/opensslv.h... no
checking for OpenSSL version >= 1.0.2... yes
checking for RAND_egd() in openssl/rand.h... no
checking for ENGINE_load_dynamic() in openssl/engine.h... yes
checking for ENGINE_load_4758cca() in openssl/engine.h... no
checking for ENGINE_load_aep() in openssl/engine.h... no
checking for ENGINE_load_atalla() in openssl/engine.h... no
checking for ENGINE_load_chil() in openssl/engine.h... no
checking for ENGINE_load_cswift() in openssl/engine.h... no
checking for ENGINE_load_nuron() in openssl/engine.h... no
checking for ENGINE_load_sureware() in openssl/engine.h... no
checking for ENGINE_load_ubsec() in openssl/engine.h... no
checking for ENGINE_load_padlock() in openssl/engine.h... no
checking for ENGINE_load_capi() in openssl/engine.h... no
checking for ENGINE_load_gmp() in openssl/engine.h... no
checking for ENGINE_load_gost() in openssl/engine.h... no
checking for ENGINE_load_cryptodev() in openssl/engine.h... yes
checking for SSL.ctx in openssl/ssl.h... no
checking for EVP_MD_CTX_new() in openssl/evp.h... yes
checking for EVP_MD_CTX_free(NULL) in openssl/evp.h... yes
checking for EVP_MD_CTX_pkey_ctx(NULL) in openssl/evp.h... yes
checking for X509_STORE_get_ex_data(NULL, 0) in openssl/x509.h... yes
checking for X509_STORE_set_ex_data(NULL, 0, NULL) in openssl/x509.h... yes
checking for X509_STORE_get_ex_new_index(0, NULL, NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_CRL_get0_signature(NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_REQ_get0_signature(NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_REVOKED_get0_serialNumber(NULL) in openssl/x509.h... yes
checking for X509_REVOKED_get0_revocationDate(NULL) in openssl/x509.h... yes
checking for X509_get0_tbs_sigalg(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_untrusted(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_cert(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_chain(NULL) in openssl/x509.h... yes
checking for OCSP_SINGLERESP_get0_id(NULL) in openssl/ocsp.h... yes
checking for SSL_CTX_get_ciphers(NULL) in openssl/ssl.h... yes
checking for X509_up_ref(NULL) in openssl/x509.h... yes
checking for X509_CRL_up_ref(NULL) in openssl/x509.h... yes
checking for X509_STORE_up_ref(NULL) in openssl/x509.h... yes
checking for SSL_SESSION_up_ref(NULL) in openssl/ssl.h... yes
checking for EVP_PKEY_up_ref(NULL) in openssl/evp.h... yes
checking for SSL_CTX_set_min_proto_version(NULL, 0) in openssl/ssl.h... yes
checking for SSL_CTX_get_security_level(NULL) in openssl/ssl.h... yes
checking for X509_get0_notBefore(NULL) in openssl/x509.h... yes
checking for SSL_SESSION_get_protocol_version(NULL) in openssl/ssl.h... yes
checking for TS_STATUS_INFO_get0_status(NULL) in openssl/ts.h... yes
checking for TS_STATUS_INFO_get0_text(NULL) in openssl/ts.h... yes
checking for TS_STATUS_INFO_get0_failure_info(NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTS_set_certs(NULL, NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTX_set_store(NULL, NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTX_add_flags(NULL, 0) in openssl/ts.h... yes
checking for TS_RESP_CTX_set_time_cb(NULL, NULL, NULL) in openssl/ts.h... yes
checking for EVP_PBE_scrypt("", 0, (unsigned char *)"", 0, 0, 0, 0, 0, NULL, 0) in openssl/evp.h... yes
checking for SSL_CTX_set_post_handshake_auth(NULL, 0) in openssl/ssl.h... yes
checking for EVP_PKEY_check(NULL) in openssl/evp.h... yes
checking for EVP_PKEY_new_raw_private_key(0, NULL, (unsigned char *)"", 0) in openssl/evp.h... yes
checking for SSL_CTX_set_ciphersuites(NULL, "") in openssl/ssl.h... yes
checking for SSL_set0_tmp_dh_pkey(NULL, NULL) in openssl/ssl.h... no
checking for ERR_get_error_all(NULL, NULL, NULL, NULL, NULL) in openssl/err.h... no
checking for TS_VERIFY_CTX_set_certs(NULL, NULL) in openssl/ts.h... no
checking for SSL_CTX_load_verify_file(NULL, "") in openssl/ssl.h... no
checking for BN_check_prime(NULL, NULL, NULL) in openssl/bn.h... no
checking for EVP_MD_CTX_get0_md(NULL) in openssl/evp.h... no
checking for EVP_MD_CTX_get_pkey_ctx(NULL) in openssl/evp.h... no
checking for EVP_PKEY_eq(NULL, NULL) in openssl/evp.h... no
checking for EVP_PKEY_dup(NULL) in openssl/evp.h... no
creating extconf.h
creating Makefile
compiling openssl_missing.c
compiling ossl_asn1.c
compiling ossl_bio.c
compiling ossl_bn.c
compiling ossl_config.c
compiling ossl_cipher.c
compiling ossl.c
compiling ossl_kdf.c
compiling ossl_digest.c
compiling ossl_engine.c
compiling ossl_hmac.c
compiling ossl_pkcs12.c
compiling ossl_pkey.c
compiling ossl_ns_spki.c
compiling ossl_pkcs7.c
compiling ossl_ocsp.c
compiling ossl_pkey_dh.c
compiling ossl_pkey_dsa.c
compiling ossl_pkey_ec.c
compiling ossl_pkey_rsa.c
compiling ossl_rand.c
compiling ossl_ssl.c
compiling ossl_ssl_session.c
compiling ossl_ts.c
compiling ossl_x509.c
compiling ossl_x509attr.c
compiling ossl_x509cert.c
compiling ossl_x509crl.c
compiling ossl_x509ext.c
compiling ossl_x509name.c
compiling ossl_x509req.c
compiling ossl_x509revoked.c
compiling ossl_x509store.c
linking shared-object openssl.bundle

Recompiling the Psych C extension (against the installed libyaml)
checking for yaml.h... yes
checking for yaml_get_version() in -lyaml... yes
creating Makefile
compiling psych.c
compiling psych_emitter.c
compiling psych_parser.c
compiling psych_to_ruby.c
compiling psych_yaml_tree.c
linking shared-object psych.bundle

TruffleRuby was successfully installed in /Users/andrykonchin/tmp/truffleruby-23.1.0
>>> Successfully installed truffleruby 23.1.0 into /Users/andrykonchin/tmp/truffleruby-23.1.0

and then

$ bin/ruby -v -e "require 'openssl'; puts 'Hello'"
truffleruby 23.1.0, like ruby 3.2.2, Oracle GraalVM Native [x86_64-darwin]
Hello

[HoneyryderChuck]

I've tried this again:

➜  ~ ruby-install -V
ruby-install: 0.9.2
➜  ~ ruby-install truffleruby -r ~/tmp
>>> Updating truffleruby versions ...
>>> Installing truffleruby 23.1.0 into /user/tmp/truffleruby-23.1.0 ...
>>> Installing dependencies for truffleruby 23.1.0 ...
Running `brew update --auto-update`...
==> Auto-updated Homebrew!
Updated 1 tap (homebrew/core).
==> New Formulae
bozohttpd                         dezoomify-rs                      python-gdbm@3.12                  python-setuptools                 python-tk@3.12                    python@3.12

You have 50 outdated formulae installed.

Warning: openssl@1.1 1.1.1w is already installed and up-to-date.
To reinstall 1.1.1w, run:
  brew reinstall openssl@1.1
Warning: libyaml 0.2.5 is already installed and up-to-date.
To reinstall 0.2.5, run:
  brew reinstall libyaml
>>> Downloading https://github.com/oracle/truffleruby/releases/download/graal-23.1.0/truffleruby-23.1.0-macos-amd64.tar.gz into /user/src ...
>>> Verifying truffleruby-23.1.0-macos-amd64.tar.gz ...
>>> Extracting truffleruby-23.1.0-macos-amd64.tar.gz to /user/src/truffleruby-23.1.0-macos-amd64 ...
>>> Installing truffleruby 23.1.0 ...
>>> Running truffleruby post-install hook ...
Recompiling the OpenSSL C extension (against the installed libssl)
checking for rb_io_maybe_wait(0, Qnil, Qnil, Qnil) in ruby/io.h... yes
checking for t_open() in -lnsl... no
checking for socket() in -lsocket... no
checking for openssl/ssl.h... yes
checking for CRYPTO_malloc() in -lcrypto... yes
checking for SSL_new() in -lssl... yes
checking for LIBRESSL_VERSION_NUMBER in openssl/opensslv.h... no
checking for OpenSSL version >= 1.0.2... yes
checking for RAND_egd() in openssl/rand.h... no
checking for ENGINE_load_dynamic() in openssl/engine.h... yes
checking for ENGINE_load_4758cca() in openssl/engine.h... no
checking for ENGINE_load_aep() in openssl/engine.h... no
checking for ENGINE_load_atalla() in openssl/engine.h... no
checking for ENGINE_load_chil() in openssl/engine.h... no
checking for ENGINE_load_cswift() in openssl/engine.h... no
checking for ENGINE_load_nuron() in openssl/engine.h... no
checking for ENGINE_load_sureware() in openssl/engine.h... no
checking for ENGINE_load_ubsec() in openssl/engine.h... no
checking for ENGINE_load_padlock() in openssl/engine.h... no
checking for ENGINE_load_capi() in openssl/engine.h... no
checking for ENGINE_load_gmp() in openssl/engine.h... no
checking for ENGINE_load_gost() in openssl/engine.h... no
checking for ENGINE_load_cryptodev() in openssl/engine.h... yes
checking for SSL.ctx in openssl/ssl.h... no
checking for EVP_MD_CTX_new() in openssl/evp.h... yes
checking for EVP_MD_CTX_free(NULL) in openssl/evp.h... yes
checking for EVP_MD_CTX_pkey_ctx(NULL) in openssl/evp.h... yes
checking for X509_STORE_get_ex_data(NULL, 0) in openssl/x509.h... yes
checking for X509_STORE_set_ex_data(NULL, 0, NULL) in openssl/x509.h... yes
checking for X509_STORE_get_ex_new_index(0, NULL, NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_CRL_get0_signature(NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_REQ_get0_signature(NULL, NULL, NULL) in openssl/x509.h... yes
checking for X509_REVOKED_get0_serialNumber(NULL) in openssl/x509.h... yes
checking for X509_REVOKED_get0_revocationDate(NULL) in openssl/x509.h... yes
checking for X509_get0_tbs_sigalg(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_untrusted(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_cert(NULL) in openssl/x509.h... yes
checking for X509_STORE_CTX_get0_chain(NULL) in openssl/x509.h... yes
checking for OCSP_SINGLERESP_get0_id(NULL) in openssl/ocsp.h... yes
checking for SSL_CTX_get_ciphers(NULL) in openssl/ssl.h... yes
checking for X509_up_ref(NULL) in openssl/x509.h... yes
checking for X509_CRL_up_ref(NULL) in openssl/x509.h... yes
checking for X509_STORE_up_ref(NULL) in openssl/x509.h... yes
checking for SSL_SESSION_up_ref(NULL) in openssl/ssl.h... yes
checking for EVP_PKEY_up_ref(NULL) in openssl/evp.h... yes
checking for SSL_CTX_set_min_proto_version(NULL, 0) in openssl/ssl.h... yes
checking for SSL_CTX_get_security_level(NULL) in openssl/ssl.h... yes
checking for X509_get0_notBefore(NULL) in openssl/x509.h... yes
checking for SSL_SESSION_get_protocol_version(NULL) in openssl/ssl.h... yes
checking for TS_STATUS_INFO_get0_status(NULL) in openssl/ts.h... yes
checking for TS_STATUS_INFO_get0_text(NULL) in openssl/ts.h... yes
checking for TS_STATUS_INFO_get0_failure_info(NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTS_set_certs(NULL, NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTX_set_store(NULL, NULL) in openssl/ts.h... yes
checking for TS_VERIFY_CTX_add_flags(NULL, 0) in openssl/ts.h... yes
checking for TS_RESP_CTX_set_time_cb(NULL, NULL, NULL) in openssl/ts.h... yes
checking for EVP_PBE_scrypt("", 0, (unsigned char *)"", 0, 0, 0, 0, 0, NULL, 0) in openssl/evp.h... yes
checking for SSL_CTX_set_post_handshake_auth(NULL, 0) in openssl/ssl.h... yes
checking for EVP_PKEY_check(NULL) in openssl/evp.h... yes
checking for EVP_PKEY_new_raw_private_key(0, NULL, (unsigned char *)"", 0) in openssl/evp.h... yes
checking for SSL_CTX_set_ciphersuites(NULL, "") in openssl/ssl.h... yes
checking for SSL_set0_tmp_dh_pkey(NULL, NULL) in openssl/ssl.h... no
checking for ERR_get_error_all(NULL, NULL, NULL, NULL, NULL) in openssl/err.h... no
checking for TS_VERIFY_CTX_set_certs(NULL, NULL) in openssl/ts.h... no
checking for SSL_CTX_load_verify_file(NULL, "") in openssl/ssl.h... no
checking for BN_check_prime(NULL, NULL, NULL) in openssl/bn.h... no
checking for EVP_MD_CTX_get0_md(NULL) in openssl/evp.h... no
checking for EVP_MD_CTX_get_pkey_ctx(NULL) in openssl/evp.h... no
checking for EVP_PKEY_eq(NULL, NULL) in openssl/evp.h... no
checking for EVP_PKEY_dup(NULL) in openssl/evp.h... no
creating extconf.h
creating Makefile
compiling openssl_missing.c
compiling ossl.c
compiling ossl_asn1.c
compiling ossl_bio.c
compiling ossl_bn.c
compiling ossl_cipher.c
compiling ossl_config.c
compiling ossl_digest.c
compiling ossl_engine.c
compiling ossl_hmac.c
compiling ossl_kdf.c
compiling ossl_ns_spki.c
compiling ossl_ocsp.c
compiling ossl_pkcs12.c
compiling ossl_pkcs7.c
compiling ossl_pkey.c
compiling ossl_pkey_dh.c
compiling ossl_pkey_dsa.c
compiling ossl_pkey_ec.c
compiling ossl_pkey_rsa.c
compiling ossl_rand.c
compiling ossl_ssl.c
compiling ossl_ssl_session.c
compiling ossl_ts.c
compiling ossl_x509.c
compiling ossl_x509attr.c
compiling ossl_x509cert.c
compiling ossl_x509crl.c
compiling ossl_x509ext.c
compiling ossl_x509name.c
compiling ossl_x509req.c
compiling ossl_x509revoked.c
compiling ossl_x509store.c
linking shared-object openssl.bundle
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete

Recompiling the Psych C extension (against the installed libyaml)
checking for yaml.h... yes
checking for yaml_get_version() in -lyaml... yes
creating Makefile
compiling psych.c
compiling psych_emitter.c
compiling psych_parser.c
compiling psych_to_ruby.c
compiling psych_yaml_tree.c
linking shared-object psych.bundle
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete

TruffleRuby was successfully installed in /user/tmp/truffleruby-23.1.0
>>> Successfully installed truffleruby 23.1.0 into /user/tmp/truffleruby-23.1.0
➜  ~ /user/tmp/truffleruby-23.1.0/bin/ruby -v
truffleruby 23.1.0, like ruby 3.2.2, Oracle GraalVM Native [x86_64-darwin]
➜  ~ /user/tmp/truffleruby-23.1.0/bin/ruby -v -e "require 'openssl'; puts 'Hello'"
truffleruby 23.1.0, like ruby 3.2.2, Oracle GraalVM Native [x86_64-darwin]
<internal:core> core/kernel.rb:260:in `require': you may need to install the system OpenSSL library libssl - see https://github.com/oracle/truffleruby/blob/master/doc/user/installing-libssl.md (dlopen(/user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle, 0x0002): Library not loaded: @rpath/libgraalvm-llvm.1.dylib (RuntimeError)
  Referenced from: <435AA929-B588-3E9B-9E9B-F2C5F858EC29> /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle
  Reason: tried: '/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/lib/libgraalvm-llvm.1.dylib' (no such file, not in dyld cache))
	from /user/tmp/truffleruby-23.1.0/lib/mri/openssl.rb:13:in `<top (required)>'
	from <internal:core> core/kernel.rb:260:in `require'
	from -e:1:in `<main>'
➜  ~

one thing to note about my environment is that I have many installations of openssl via homebrew, besides the outdated system one

brew list | grep openssl
openssl@1.1
openssl@3

where openssl@3 is set via brew --prefix .Not sure if the truffleruby installation script is bypassing this(?).

[eregon]

Could you write here your macOS version and XCode version? It seems like those differ from @andrykonchin and our CI and might be the cause of this issue.
Notably those warnings sound like the GraalVM LLVM Toolchain and the macOS system linker are far apart:

-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete
-macosx_version_min has been renamed to -macos_version_min
ld: warning: -multiply_defined is obsolete

@rschatz @lewurm maybe you have seen this before?

(Apple is unfortunately known for making incompatible changes in their C toolchain almost every macOS major release)

➜  ~ /user/tmp/truffleruby-23.1.0/bin/ruby -v -e "require 'openssl'; puts 'Hello'"
truffleruby 23.1.0, like ruby 3.2.2, Oracle GraalVM Native [x86_64-darwin]
<internal:core> core/kernel.rb:260:in `require': you may need to install the system OpenSSL library libssl - see https://github.com/oracle/truffleruby/blob/master/doc/user/installing-libssl.md (dlopen(/user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle, 0x0002): Library not loaded: @rpath/libgraalvm-llvm.1.dylib (RuntimeError)
  Referenced from: <435AA929-B588-3E9B-9E9B-F2C5F858EC29> /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle
  Reason: tried: '/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/System/Volumes/Preboot/Cryptexes/OS/usr/local/opt/openssl@1.1/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/local/lib/libgraalvm-llvm.1.dylib' (no such file), '/usr/lib/libgraalvm-llvm.1.dylib' (no such file, not in dyld cache))
	from /user/tmp/truffleruby-23.1.0/lib/mri/openssl.rb:13:in `<top (required)>'
	from <internal:core> core/kernel.rb:260:in `require'
	from -e:1:in `<main>'

This sounds like openssl.bundle is loaded natively and not on Sulong, I wonder if Sulong doesn't detect that .bundle as having a valid header or so, or if the bitcode is actually missing in openssl.bundle (ideally Sulong would error in such a case rather than load natively but IIRC that's not the current behavior, maybe this could be solved via different mime-types for user one and for dependencies).
@rschatz Could you advise some command lines to figure that out?

where openssl@3 is set via brew --prefix .Not sure if the truffleruby installation script is bypassing this(?).

TruffleRuby will pick one of them, that should just work.
It currently prefers 1.1: https://github.com/oracle/truffleruby/blob/master/lib/truffle/truffle/openssl-prefix.rb

[rschatz]

@rschatz Could you advise some command lines to figure that out?

mx extract-bitcode <path-to-so-file> should produce a .so.bc file next to the .so file containing the bitcode, if the bitcode is there. It's using exactly the same code as Sulong uses to extract the bitcode, so if this works, the bitcode is there and can be found by Sulong. If it doesn't work, the bitcode is at least not in the place where Sulong is looking for it.

[eregon]

@HoneyryderChuck Could you try that?
Here are the full instructions:

mkdir truffleruby-ws
cd truffleruby-ws
git clone https://github.com/graalvm/mx.git
git clone https://github.com/oracle/graal.git
cd graal
../mx/mx extract-bitcode /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle

Could you also copy the output of: otool -l /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle?

[eregon]

@lewurm had a similar-looking error, with XCode 15 which ships a new linker and that apparently makes https://github.com/oracle/graal/blob/3fe9ebac47c4b850068770c5e7afe419ba426a39/sulong/projects/com.oracle.truffle.llvm.parser/src/com/oracle/truffle/llvm/parser/macho/MachOFile.java#L118 fail to find the bitcode.

[lewurm]

as a workaround using an older Xcode should do the job.

[HoneyryderChuck]

Could you write here your macOS version and XCode version?

Ventura 13.5.2, XCode 15

Could you also copy the output of: otool -l /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle?

"no primary suite found for extract-bitcode"

as a workaround using an older Xcode should do the job.

Isn't there a workaround for XCode 15, where I can do smth manually instead? Unfortunately downgrading xcode is not feasible or an option. I'll have to wait for a fix otherwise.

[eregon]

"no primary suite found for extract-bitcode"

Ah, I forgot cd sulong or truffleruby after cd graal so it should be like:

mkdir truffleruby-ws
cd truffleruby-ws
git clone https://github.com/oracle/truffleruby.git
cd truffleruby
bin/jt build
bin/jt mx build
bin/jt mx extract-bitcode /user/tmp/truffleruby-23.1.0/lib/mri/openssl.bundle

Isn't there a workaround for XCode 15, where I can do smth manually instead? Unfortunately downgrading xcode is not feasible or an option. I'll have to wait for a fix otherwise.

We're looking into it, there are other likely related issues with XCode 15 reproduced by others, we'll need to fix this on Sulong master anyway.