Ruby-build: Ruby 2.4.1 build failed on macOS Sierra 10.12.3

Created on 26 Mar 2017  ·  23Comments  ·  Source: rbenv/ruby-build

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?

picture wissamir
👍4

Most helpful comment

I had same issue after migration to new macbook pro using peer to peer migration, looks like Homebrew env crashed.
I fixed it by delete the brew include files:
sudo mv /usr/local/include /usr/local/include_old

picture wkang on 21 Aug 2018
👍17 ❤7 🎉7

All 23 comments

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

hsbt picture hsbt on 27 Mar 2017

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?

wissamir picture wissamir on 27 Mar 2017

Exactly the same problem here. Versions:

  • rbenv 1.1.0
  • ruby-build 20170201
  • openssl: stable 1.0.2k
  • osx 10.12.4
shuriu picture shuriu on 29 Mar 2017

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

wissamir picture wissamir on 31 Mar 2017

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
SandroGrzicic picture SandroGrzicic on 5 Apr 2017

Same problem here, can't install 2.4.1

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

masayhiro picture masayhiro on 21 Apr 2017

https://github.com/Homebrew/brew/pull/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

yueyangwu picture yueyangwu on 21 Apr 2017
👍4

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

masayhiro picture masayhiro on 21 Apr 2017

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 [email protected]
$ rbenv install 2.4.1
...
Installed ruby-2.4.1 to /Users/Florian/.rbenv/versions/2.4.1
mwxclauss picture mwxclauss on 28 Apr 2017

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
kasunt-nixdev picture kasunt-nixdev on 3 May 2017

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:

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

  6. 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
  7. Profit! rbenv install 2.4.1
shuriu picture shuriu on 3 May 2017
🎉15 👍2

@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.

mislav picture mislav on 3 May 2017

@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

wissamir picture wissamir on 14 May 2017

@shuriu your solution worked for me. Thank You.

gopumon picture gopumon on 14 Jul 2017
👍1

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 [email protected]). 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/[email protected]/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).

sintro picture sintro on 11 Aug 2017
👍3

I use MacPorts, and I solved this by exporting my PATH variable to only include items from rbenv and the system.

$ export PATH=/Users/john/.rbenv/shims:/Users/john/.rbenv/bin:/usr/bin:/bin:/usr/sbin:/sbin
$ rbenv install 2.4.1
Downloading openssl-1.1.0f.tar.gz...
-> https://dqw8nmjcqpjn7.cloudfront.net/12f746f3f2493b2f39da7ecf63d7ee19c6ac9ec6a4fcd8c229da8a522cb12765
Installing openssl-1.1.0f...
Installed openssl-1.1.0f to /Users/john/.rbenv/versions/2.4.1

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...
Installed ruby-2.4.1 to /Users/john/.rbenv/versions/2.4.1
johndouthat picture johndouthat on 17 Aug 2017

I was Unable to install ruby 2.4.1 with openssl but I I was able to install with [email protected]

  1. brew uninstall openssl --ignore-dependencies I had a 1.0.1l version.
  2. brew cleanup
  3. brew install [email protected] installed [email protected]: stable 1.1.0f (bottled) [keg-only]
  4. export PATH="/usr/local/opt/[email protected]/bin:$PATH" in my ~/.bashrc file
  5. rbenv install 2.4.1 (previously upgraded ruby-build)

It seems the install downloaded openssl as part of ruby installation. Does that mean ruby-build did not use the [email protected] installed in previous step?

My install output shows

$ rbenv install 2.4.1
Downloading openssl-1.1.0f.tar.gz...
-> https://dqw8nmjcqpjn7.cloudfront.net/12f746f3f2493b2f39da7ecf63d7ee19c6ac9ec6a4fcd8c229da8a522cb12765
Installing openssl-1.1.0f...
Installed openssl-1.1.0f to /Users/marekj/.rbenv/versions/2.4.1

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...
ruby-build: use readline from homebrew
Installed ruby-2.4.1 to /Users/marekj/.rbenv/versions/2.4.1

When I type brew missing I still see I am missing openssl even if I have [email protected] installed and PATH to it set.

$ brew missing
libevent: openssl
libssh: openssl
libssh2: openssl
mongodb: openssl
nmap: openssl
openssl-osx-ca: openssl
phantomjs: openssl
postgresql: openssl
rbenv: openssl
ruby: openssl
ruby-build: openssl
tmate: openssl
tmux: openssl
marekj picture marekj on 18 Aug 2017
👍1

Thanks a lot.

The solution from @sintro to install the curl works for me.

pukuldua picture pukuldua on 10 Sep 2017

Struggling with getting rbenv up and running on my mac:

macOS 10.13.2
rbenv 1.1.1
OpenSSL 1.1.0g 2 Nov 2017
curl 7.57.0

% which rbenv
/usr/local/bin/rbenv
% which openssl
/usr/local/opt/[email protected]/bin/openssl
% which curl
/usr/local/opt/curl/bin/curl

rbenv, curl, openssl - all in PATH

% 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 10.13.2 using ruby-build 20171215)

Inspect or clean up the working tree at /var/folders/31/41tck3qx69scnynksxc_38ch0000gn/T/ruby-build.20171220150125.94300
Results logged to /var/folders/31/41tck3qx69scnynksxc_38ch0000gn/T/ruby-build.20171220150125.94300.log

Last 10 log lines:
checking for long long... yes
checking for off_t... yes
checking char bit... 8
checking size of int... 0
checking size of short... 0
checking size of long... 0
checking size of long long... configure: error: in `/var/folders/31/41tck3qx69scnynksxc_38ch0000gn/T/ruby-build.20171220150125.94300/ruby-2.4.1':
configure: error: cannot compute sizeof (long long)
See `config.log' for more details
make: *** No targets specified and no makefile found.  Stop.

Tried all solutions listed above - nothing helped.
Any suggestion?

nishanov picture nishanov on 20 Dec 2017

I was having the same issue.

MacOS Version 10.13.2 (17C88)
Ruby 2.4.2
OpenSSL 1.0.2n

I resolved with 

brew update && brew upgrade openssl
export LDFLAGS="-L/usr/local/opt/openssl/lib"
export CPPFLAGS="-I/usr/local/opt/openssl/include"
export PKG_CONFIG_PATH="/usr/local/opt/openssl/lib/pkgconfig"
brew upgrade ruby-build
rbenv install 2.4.2
michaelbrawn picture michaelbrawn on 21 Dec 2017
👍4

I had same issue after migration to new macbook pro using peer to peer migration, looks like Homebrew env crashed.
I fixed it by delete the brew include files:
sudo mv /usr/local/include /usr/local/include_old

wkang picture wkang on 21 Aug 2018
👍17 ❤7 🎉7

Thanks everyone for sharing your workarounds!

Closing due to staleness. Hopefully people don't have this problem anymore.

mislav picture mislav on 12 Feb 2019
👎4

I had same issue after migration to new macbook pro using peer to peer migration, looks like Homebrew env crashed.
I fixed it by delete the brew include files:
sudo mv /usr/local/include /usr/local/include_old

In order for me to do this on macOS Catalina I had to:

  1. Disable SIP (System Integrity Protection) by rebooting into Recovery Mode and running csrutil disable in the Terminal.

  2. Remount root as a writable volume with sudo mount -uw /.

joshuapinter picture joshuapinter on 27 Oct 2019
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