How to install a new Ruby version on Mac OS

Question

I'm trying to install Ruby v2.7.0 on Mac OS Mojave v10.14.6 with rbenv by running rbenv install 2.7.0 and I get the following error:

Downloading openssl-1.1.1d.tar.gz...
-> https://dqw8nmjcqpjn7.cloudfront.net/1e3a91bc1f9dfce01af26026f856e064eab4c8ee0a8f457b5ae30b40b8b711f2
Installing openssl-1.1.1d...

BUILD FAILED (OS X 10.14.6 using ruby-build 20200224)

Inspect or clean up the working tree at /var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.8ElfaA
Results logged to /var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.log

Last 10 log lines:
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/bf_prefix.d.tmp -MT apps/bf_prefix.o -c -o apps/bf_prefix.o apps/bf_prefix.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/opt.d.tmp -MT apps/opt.o -c -o apps/opt.o apps/opt.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/s_cb.d.tmp -MT apps/s_cb.o -c -o apps/s_cb.o apps/s_cb.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/s_socket.d.tmp -MT apps/s_socket.o -c -o apps/s_socket.o apps/s_socket.c
ar r apps/libapps.a apps/app_rand.o apps/apps.o apps/bf_prefix.o apps/opt.o apps/s_cb.o apps/s_socket.o
ar: creating archive apps/libapps.a
/usr/local/Cellar/cctools/855/bin/ranlib: object: apps/libapps.a(app_rand.o) malformed object (unknown load command 1)
ar: internal ranlib command failed
make[1]: *** [apps/libapps.a] Error 1
make: *** [all] Error 2

The log file (/var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.log) looks like this:

/var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.8ElfaA ~/Documents/launch_school
HTTP/1.1 200 OK
Content-Type: binary/octet-stream
Content-Length: 8845861
Connection: keep-alive
Last-Modified: Tue, 01 Oct 2019 21:38:26 GMT
Accept-Ranges: bytes
Server: AmazonS3
Date: Tue, 03 Mar 2020 02:47:54 GMT
ETag: "3be209000dbc7e1b95bcdf47980a3baa"
X-Cache: Hit from cloudfront
Via: 1.1 cec03b477881661a098cf57a0142e58d.cloudfront.net (CloudFront)
X-Amz-Cf-Pop: NRT51-C2
X-Amz-Cf-Id: tuC_K1W4DW9QlEqV60T5WHbOCqvd5-ZAi7HeVNYW0mGCXxO9pKkpyQ==
Age: 44228

/var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.8ElfaA/openssl-1.1.1d /var/folders/qz/072qbsw163lb8p511v4dtssr0000gq/T/ruby-build.20200304000500.19560.8ElfaA ~/Documents/launch_school
Operating system: x86_64-apple-darwinDarwin Kernel Version 18.7.0: Thu Jan 23 06:52:12 PST 2020; root:xnu-4903.278.25~1/RELEASE_X86_64
Configuring OpenSSL version 1.1.1d (0x1010104fL) for darwin64-x86_64-cc
Using os-specific seed configuration
Creating configdata.pm
Creating Makefile

**********************************************************************
***                                                                ***
***   OpenSSL has been successfully configured                     ***
***                                                                ***
***   If you encounter a problem while building, please open an    ***
***   issue on GitHub <https://github.com/openssl/openssl/issues>  ***
***   and include the output from the following command:           ***
***                                                                ***
***       perl configdata.pm --dump                                ***
***                                                                ***
***   (If you are new to OpenSSL, you might want to consult the    ***
***   'Troubleshooting' section in the INSTALL file first)         ***
***                                                                ***
**********************************************************************
WARNING! If you wish to build 32-bit libraries, then you have to
         invoke 'KERNEL_BITS=32 ./config  '--prefix=/Users/<username>/.rbenv/versions/2.7.0/openssl' '--openssldir=/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl' 'zlib-dynamic' 'no-ssl3' 'shared''.
/usr/local/Cellar/perl/5.26.2/bin/perl "-I." -Mconfigdata "util/dofile.pl" \
      "-oMakefile" crypto/include/internal/bn_conf.h.in > crypto/include/internal/bn_conf.h
/usr/local/Cellar/perl/5.26.2/bin/perl "-I." -Mconfigdata "util/dofile.pl" \
      "-oMakefile" crypto/include/internal/dso_conf.h.in > crypto/include/internal/dso_conf.h
/usr/local/Cellar/perl/5.26.2/bin/perl "-I." -Mconfigdata "util/dofile.pl" \
      "-oMakefile" include/openssl/opensslconf.h.in > include/openssl/opensslconf.h
make depend && make _all
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/app_rand.d.tmp -MT apps/app_rand.o -c -o apps/app_rand.o apps/app_rand.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/apps.d.tmp -MT apps/apps.o -c -o apps/apps.o apps/apps.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/bf_prefix.d.tmp -MT apps/bf_prefix.o -c -o apps/bf_prefix.o apps/bf_prefix.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/opt.d.tmp -MT apps/opt.o -c -o apps/opt.o apps/opt.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/s_cb.d.tmp -MT apps/s_cb.o -c -o apps/s_cb.o apps/s_cb.c
clang  -I. -Iinclude -fPIC -arch x86_64 -O3 -Wall -DL_ENDIAN -DOPENSSL_PIC -DOPENSSL_CPUID_OBJ -DOPENSSL_IA32_SSE2 -DOPENSSL_BN_ASM_MONT -DOPENSSL_BN_ASM_MONT5 -DOPENSSL_BN_ASM_GF2m -DSHA1_ASM -DSHA256_ASM -DSHA512_ASM -DKECCAK1600_ASM -DRC4_ASM -DMD5_ASM -DVPAES_ASM -DGHASH_ASM -DECP_NISTZ256_ASM -DX25519_ASM -DPOLY1305_ASM -DOPENSSLDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/ssl\"" -DENGINESDIR="\"/Users/<username>/.rbenv/versions/2.7.0/openssl/lib/engines-1.1\"" -D_REENTRANT -DZLIB -DZLIB_SHARED -DNDEBUG -I/Users/<username>/.rbenv/versions/2.7.0/include -MMD -MF apps/s_socket.d.tmp -MT apps/s_socket.o -c -o apps/s_socket.o apps/s_socket.c
ar r apps/libapps.a apps/app_rand.o apps/apps.o apps/bf_prefix.o apps/opt.o apps/s_cb.o apps/s_socket.o
ar: creating archive apps/libapps.a
/usr/local/Cellar/cctools/855/bin/ranlib: object: apps/libapps.a(app_rand.o) malformed object (unknown load command 1)
ar: internal ranlib command failed
make[1]: *** [apps/libapps.a] Error 1
make: *** [all] Error 2

The steps I have taken so far are:

Updated the ruby-build rbenv plugin which is required to install Ruby via rbenv.
Installed the latest version of Xcode along with the latest version of its Command Line Tools as suggested in "How to fix ranlib/libtool error when running make".
Uninstalled MacPorts as suggested in "Arm64 problem while configure" by following "Uninstall MacPorts".

Note: The initial question I posted was closed due to it being labeled as "off-topic". I hope this one continues to stay open so people can provide and reference the solution(s) to the problem discussed above.

To close voters: Questions about how to install and use developer specific tools are on-topic for SO. — Wayne Conrad, Mar 03 '20 at 15:58
Possible duplicate: [Cannot install any version of ruby on Mojave - internal ranlib command failed](https://stackoverflow.com/q/54363030/1380680) — Reinier Torenbeek, Mar 03 '20 at 16:38

How to install a new Ruby version on Mac OS

0 Answers0