Ruby 2.4.1 build failed on macOS Sierra 10.12.3

[wissamir]

Ruby 2.4.1 build fails on macOS Sierra 10.12.3, below the log I got

rbenv install 2.4.1
ruby-build: use openssl from homebrew
Downloading ruby-2.4.1.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.1.tar.bz2
Installing ruby-2.4.1...

BUILD FAILED (OS X 10.12.3 using ruby-build 20170201)

Inspect or clean up the working tree at /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170326214012.36750
Results logged to /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170326214012.36750.log

Last 10 log lines:
../.././include/ruby/ruby.h:2166:6: note: expanded from macro 'rb_scan_args_count_block'
     rb_scan_args_count_end(fmt, ofs, varc, vari) : \
     ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:2162:12: note: expanded from macro 'rb_scan_args_count_end'
    ((vari)/(!fmt[ofs] || rb_scan_args_bad_format(fmt)))
           ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

cat /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170326214012.36750.log | grep -i error
checking for ERRORFUNC function attribute... x
checking for strerror... yes
	CFLAGS = -O3 -Wno-error=shorten-64-to-32  -pipe
compiling error.c
compiling regerror.c
compiling dataerror.c
ossl_x509store.c:175:16: error: member reference type 'int' is not a pointer
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

my openssl is the latest:

brew info openssl
openssl: stable 1.0.2k (bottled) [keg-only]
SSL/TLS cryptography library
https://openssl.org/
/usr/local/Cellar/openssl/1.0.2d_1 (1,638 files, 12.1M)
  Poured from bottle on 2015-07-13 at 20:46:23
/usr/local/Cellar/openssl/1.0.2k (1,696 files, 12M)
  Poured from bottle on 2017-02-03 at 07:32:39
From: https://github.com/Homebrew/homebrew-core/blob/master/Formula/openssl.rb
==> Dependencies
Build: makedepend ✘
==> Options
--universal
	Build a universal binary
--without-test
	Skip build-time tests (not recommended)
==> Caveats
A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

If you need to have this software first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include
For pkg-config to find this software you may need to set:
    PKG_CONFIG_PATH: /usr/local/opt/openssl/lib/pkgconfig

brew upgrade openssl
Updating Homebrew...
==> Auto-updated Homebrew!
Updated 1 tap (homebrew/core).
==> Updated Formulae
bash-git-prompt                                              checkstyle                                                   idris

Error: openssl 1.0.2k already installed

Any suggestion?

[hsbt]

I couldn't reproduce it. Can you remove old version of openssl that is 1.0.2d_1 ?

[wissamir]

I removed version 1.0.2d_1 but the problem persists

brew info openssl
openssl: stable 1.0.2k (bottled) [keg-only]
SSL/TLS cryptography library
https://openssl.org/
/usr/local/Cellar/openssl/1.0.2k (1,696 files, 12MB)
  Poured from bottle on 2017-02-03 at 07:32:39
From: https://github.com/Homebrew/homebrew-core/blob/master/Formula/openssl.rb
==> Dependencies
Build: makedepend ✘
==> Options
--universal
	Build a universal binary
--without-test
	Skip build-time tests (not recommended)
==> Caveats
A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

If you need to have this software first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include
For pkg-config to find this software you may need to set:
    PKG_CONFIG_PATH: /usr/local/opt/openssl/lib/pkgconfig


rbenv install 2.4.1
ruby-build: use openssl from homebrew
Downloading ruby-2.4.1.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.1.tar.bz2
Installing ruby-2.4.1...

BUILD FAILED (OS X 10.12.3 using ruby-build 20170201)

Inspect or clean up the working tree at /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170327162603.1464
Results logged to /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170327162603.1464.log

Last 10 log lines:
../.././include/ruby/ruby.h:2166:6: note: expanded from macro 'rb_scan_args_count_block'
     rb_scan_args_count_end(fmt, ofs, varc, vari) : \
     ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:2162:12: note: expanded from macro 'rb_scan_args_count_end'
    ((vari)/(!fmt[ofs] || rb_scan_args_bad_format(fmt)))
           ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

cat /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170327162603.1464.log | grep -i error
checking for ERRORFUNC function attribute... x
checking for strerror... yes
	CFLAGS = -O3 -Wno-error=shorten-64-to-32  -pipe
compiling error.c
compiling regerror.c
compiling dataerror.c
ossl_x509store.c:175:16: error: member reference type 'int' is not a pointer
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

any other suggestions please?

[stfcodes]

Exactly the same problem here. Versions:

• rbenv 1.1.0
• ruby-build 20170201
• openssl: stable 1.0.2k
• osx 10.12.4

[wissamir]

Any update on this issue please?
I tried to totally remove openssl, ruby-build, rbenv and restart from scratch, letting hombrew install all required dependencies, but problem remains the same.
Might be worth mentioning that same problem occurs also when trying to build ruby 2.4.0, 2.4.0-preview1, 2.4.0-preview2, 2.4.0-preview3, 2.4.0-rc1, 2.4.0-dev, 2.5.0-dev (below some of the output, fails always on "ossl_x509store.c:175:16: error: member reference type 'int' is not a pointer")

Whereas build succeeds for 2.3.3 (and beyond)

brew install rbenv
Updating Homebrew...
==> Auto-updated Homebrew!
Updated 1 tap (homebrew/core).
==> Updated Formulae
ats2-postiats                                                                              sqlite

==> Installing dependencies for rbenv: openssl, ruby-build
==> Installing rbenv dependency: openssl
==> Downloading https://homebrew.bintray.com/bottles/openssl-1.0.2k.sierra.bottle.tar.gz
Already downloaded: /Users/wissamabuahmad/Library/Caches/Homebrew/openssl-1.0.2k.sierra.bottle.tar.gz
==> Pouring openssl-1.0.2k.sierra.bottle.tar.gz
==> Using the sandbox
==> Caveats
A CA file has been bootstrapped using certificates from the SystemRoots
keychain. To add additional certificates (e.g. the certificates added in
the System keychain), place .pem files in
  /usr/local/etc/openssl/certs

and run
  /usr/local/opt/openssl/bin/c_rehash

This formula is keg-only, which means it was not symlinked into /usr/local.

Apple has deprecated use of OpenSSL in favor of its own TLS and crypto libraries

If you need to have this software first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.bash_profile

For compilers to find this software you may need to set:
    LDFLAGS:  -L/usr/local/opt/openssl/lib
    CPPFLAGS: -I/usr/local/opt/openssl/include
For pkg-config to find this software you may need to set:
    PKG_CONFIG_PATH: /usr/local/opt/openssl/lib/pkgconfig

==> Summary
🍺  /usr/local/Cellar/openssl/1.0.2k: 1,696 files, 12MB
==> Installing rbenv dependency: ruby-build
==> Downloading https://github.com/rbenv/ruby-build/archive/v20170322.tar.gz
Already downloaded: /Users/wissamabuahmad/Library/Caches/Homebrew/ruby-build-20170322.tar.gz
==> ./install.sh
🍺  /usr/local/Cellar/ruby-build/20170322: 339 files, 180.9KB, built in 1 second
==> Installing rbenv
==> Downloading https://homebrew.bintray.com/bottles/rbenv-1.1.0.sierra.bottle.tar.gz
Already downloaded: /Users/wissamabuahmad/Library/Caches/Homebrew/rbenv-1.1.0.sierra.bottle.tar.gz
==> Pouring rbenv-1.1.0.sierra.bottle.tar.gz
🍺  /usr/local/Cellar/rbenv/1.1.0: 36 files, 63.2KB


rbenv install 2.4.1
ruby-build: use openssl from homebrew
Downloading ruby-2.4.1.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.1.tar.bz2
Installing ruby-2.4.1...

BUILD FAILED (OS X 10.12.3 using ruby-build 20170201)

Inspect or clean up the working tree at /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331121219.32992
Results logged to /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331121219.32992.log

Last 10 log lines:
../.././include/ruby/ruby.h:2166:6: note: expanded from macro 'rb_scan_args_count_block'
     rb_scan_args_count_end(fmt, ofs, varc, vari) : \
     ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:2162:12: note: expanded from macro 'rb_scan_args_count_end'
    ((vari)/(!fmt[ofs] || rb_scan_args_bad_format(fmt)))
           ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

more /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331121219.32992.log | grep -i error
checking for ERRORFUNC function attribute... x
checking for strerror... yes
	CFLAGS = -O3 -Wno-error=shorten-64-to-32  -pipe
compiling error.c
compiling regerror.c
compiling dataerror.c
ossl_x509store.c:175:16: error: member reference type 'int' is not a pointer
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2




rbenv install 2.4.0
ruby-build: use openssl from homebrew
Downloading ruby-2.4.0.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.0.tar.bz2
Installing ruby-2.4.0...

BUILD FAILED (OS X 10.12.3 using ruby-build 20170201)

Inspect or clean up the working tree at /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331122046.54791
Results logged to /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331122046.54791.log

Last 10 log lines:
../.././include/ruby/ruby.h:2162:6: note: expanded from macro 'rb_scan_args_count_block'
     rb_scan_args_count_end(fmt, ofs, varc, vari) : \
     ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:2158:12: note: expanded from macro 'rb_scan_args_count_end'
    ((vari)/(!fmt[ofs] || rb_scan_args_bad_format(fmt)))
           ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2


cat /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331122046.54791.log | grep -i error
checking for ERRORFUNC function attribute... x
checking for strerror... yes
	CFLAGS = -O3 -Wno-error=shorten-64-to-32  -pipe
compiling error.c
compiling regerror.c
compiling dataerror.c
ossl_x509store.c:175:16: error: member reference type 'int' is not a pointer
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2


rbenv install 2.4.0-preview3
ruby-build: use openssl from homebrew
Downloading ruby-2.4.0-preview3.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.4/ruby-2.4.0-preview3.tar.bz2
Installing ruby-2.4.0-preview3...

BUILD FAILED (OS X 10.12.3 using ruby-build 20170201)

Inspect or clean up the working tree at /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331123039.76523
Results logged to /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331123039.76523.log

Last 10 log lines:
../.././include/ruby/ruby.h:2155:6: note: expanded from macro 'rb_scan_args_count_block'
     rb_scan_args_count_end(fmt, ofs, varc, vari) : \
     ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:2151:12: note: expanded from macro 'rb_scan_args_count_end'
    ((vari)/(!fmt[ofs] || rb_scan_args_bad_format(fmt)))
           ^~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

cat /var/folders/j2/90b3sd_j3fqcgc2yxp_wwc600000gq/T/ruby-build.20170331123039.76523.log | grep -i error
checking whether -Werror=implicit-int is accepted as CFLAGS... yes
checking whether -Werror=pointer-arith is accepted as CFLAGS... yes
checking whether -Werror=write-strings is accepted as CFLAGS... yes
checking whether -Werror=declaration-after-statement is accepted as CFLAGS... yes
checking whether -Werror=shorten-64-to-32 is accepted as CFLAGS... yes
checking whether -Werror=implicit-function-declaration is accepted as CFLAGS... yes
checking whether -Werror=division-by-zero is accepted as CFLAGS... yes
checking whether -Werror=deprecated-declarations is accepted as CFLAGS... yes
checking whether -Werror=extra-tokens is accepted as CFLAGS... yes
checking for ERRORFUNC function attribute... x
checking for strerror... yes
                          -Wunused-variable -Werror=implicit-int \
                          -Werror=pointer-arith -Werror=write-strings \
                          -Werror=declaration-after-statement \
                          -Werror=shorten-64-to-32 \
                          -Werror=implicit-function-declaration \
                          -Werror=division-by-zero \
                          -Werror=deprecated-declarations \
                          -Werror=extra-tokens
	CFLAGS = -O3 -Wno-error=shorten-64-to-32  -pipe
compiling error.c
compiling regerror.c
compiling dataerror.c
ossl_x509store.c:116:16: error: member reference type 'int' is not a pointer
13 warnings and 1 error generated.
make[2]: *** [ossl_x509store.o] Error 1
make[1]: *** [ext/openssl/all] Error 2
make: *** [build-ext] Error 2

[SandroGrzicic]

Same issue here, 2.4.1 didn't work, 2.3.3 works.

• rbenv 1.1.0
• ruby-build 20170201
• OpenSSL 1.0.1h 5 Jun 2014
• MacOS 10.12.3
• XCode 8.3

[masayhiro]

Same problem here, can't install 2.4.1

MacOS X 10.12.3
Xcode 8.3
ruby-build 20170322
OpenSSL 1.0.2k

[yueyangwu]

Homebrew/brew#597

Here is the solution!!!!!!!! It works for me!
brew update
brew install openssl
ln -s /usr/local/opt/openssl/lib/libcrypto.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/opt/openssl/lib/libssl.1.0.0.dylib /usr/local/lib/
ln -s /usr/local/Cellar/openssl/1.0.2j/bin/openssl openssl
ln -s /usr/local/share/dotnet/dotnet /usr/local/bin/dotnet

[masayhiro]

Thanks a lot.

In my case, I updated OS X n problem solved. Hopefully, this will work...

MacOS X 10.12.4
Xcode8.3
ruby-build 20170322
OpenSSL 1.0.2k

[mwxclauss]

I had the same problem. This is what I did, but I'm not sure which step the error solved. My assumption is, that an old macport based version of openssl triggered the conflict.

$ rbenv install 2.4.1
BUILD FAILED (OS X 10.12.4 using ruby-build 20170322)
...
$ brew uninstall --force openssl
$ brew update && brew upgrade && brew cleanup && brew doctor
$ sudo rm -rf /opt/local
$ sudo rm -rf /Applications/DarwinPorts
$ sudo rm -rf /Applications/MacPorts
$ sudo rm -rf /Library/LaunchDaemons/org.macports.*
$ sudo rm -rf /Library/Receipts/DarwinPorts*.pkg
$ sudo rm -rf /Library/Receipts/MacPorts*.pkg
$ sudo rm -rf /Library/StartupItems/DarwinPortsStartup
$ sudo rm -rf /Library/Tcl/darwinports1.0
$ sudo rm -rf /Library/Tcl/macports1.0
$ sudo rm -rf ~/.macports
$ brew install --force openssl@1.1
$ rbenv install 2.4.1
...
Installed ruby-2.4.1 to /Users/Florian/.rbenv/versions/2.4.1

[day0ops]

I had a similar issue. Turned out that I had the following in my .bash_profile. Commenting it out fixed my issues. I have a feeling this led to some conflicts with system libraries

#export LIBRARY_PATH=/opt/local/lib:/usr/local/lib

[stfcodes]

I fixed my issue. It was because of a leftover openssl install, plus some missing ENV variables that appeared in later brew openssl versions. In any case:

0. brew update
1. brew unlink openssl
2. brew uninstall --ignore-dependencies openssl
3. Repeat 2. until openssl is completely nuked
4. brew install openssl
5. Follow post install instructions:

   If you need to have this software first in your PATH run:
     echo 'export PATH="/usr/local/opt/openssl/bin:$PATH"' >> ~/.zshrc
   
   For compilers to find this software you may need to set:
       LDFLAGS:  -L/usr/local/opt/openssl/lib
       CPPFLAGS: -I/usr/local/opt/openssl/include
   For pkg-config to find this software you may need to set:
       PKG_CONFIG_PATH: /usr/local/opt/openssl/lib/pkgconfig
   

6. Profit! rbenv install 2.4.1

[mislav]

@wissamir Have you ever solved this? Ruby 2.4.1 compiles fine for me on Sierra with latest Homebrew and its openssl 1.0.2k. Check that you don't have another openssl left over from macports or some other system.

[wissamir]

@mislav, I've just tried this... yes I can confirm that workarounds explained above solve the issue also for me
I had to pay attention to old openssl versions installed by macports and remove also those
Many thanks

[gopumon]

@shuriu your solution worked for me. Thank You.

[sintro]

even after using @mwxclauss solution (and @shuriu), you will probably still get BUILD ERROR with line like

SSL23_GET_SERVER_HELLO:tlsv1 alert protocol version

The reason is because rbenv still use old system "curl", which knows nothing about your new "openssl v 1.1" (I used brew install openssl@1.1). For me, installing new version of curl with brew did the work:

brew install curl

Then add installed curl to your PATH (before default path, which is /usr/bin), and ensure that openssl of actual brew's version is also there:

export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"
export PATH="/usr/local/opt/curl/bin:$PATH"

You can make sure after relaunch of terminal that latest versions of this programs will be used by trying

which -a openssl
which -a curl
openssl version -a
curl -V

First two commands should output all paths with the programs, but top ones should be brew versions. Last two commands should show latest versions of programs (1.1.0f and 7.55 for me now).