ruby-install fails when installing ruby 2.6.x and 3.0.x on mac osx 11.6

Question

When running ruby-install, it fails to build. This also reported in rbenv issues (https://github.com/rbenv/ruby-build/issues/1725).

for example when installing ruby 2.6.8

# installing via ruby-install ( https://github.com/postmodern/ruby-install )
ruby-install ruby 2.6.8

it results in the following error

ossl_x509store.c:452:30: note: ')' token is here
    result = rb_funcall(ctx, rb_intern("verify"), 0);
                             ^~~~~~~~~~~~~~~~~~~
../.././include/ruby/ruby.h:1826:56: note: expanded from macro 'rb_intern'
        __extension__ (RUBY_CONST_ID_CACHE((ID), (str))) : \
                                                       ^
../.././include/ruby/ruby.h:2602:20: note: expanded from macro 'rb_funcall'
        rb_funcallv(recv, mid, \
                          ^~~
6 warnings generated.
linking shared-object openssl.bundle
installing default openssl libraries
make[2]: Leaving directory '/Users/xxxxx/src/ruby-2.6.8/ext/openssl'
make[2]: Entering directory '/Users/xxxxx/src/ruby-2.6.8/ext/ripper'
extracting ripper.y from ../.././parse.y
compiling compiler ripper.y
ripper.y:762.9-16: syntax error, unexpected identifier, expecting string
make[2]: *** [Makefile:332: ripper.c] Error 1
make[2]: Leaving directory '/Users/xxxxx/src/ruby-2.6.8/ext/ripper'
make[1]: *** [exts.mk:257: ext/ripper/all] Error 2
make[1]: Leaving directory '/Users/xxxxx/src/ruby-2.6.8'
make: *** [uncommon.mk:286: build-ext] Error 2
!!! Compiling ruby 2.6.8 failed!

Answer 1

Seems to be a compiler issue. First ensure that Xcode is installed appropriately. In my case, I had it installed already but you can opt to reinstall to be sure. hope this helps people save time trying to figure out the issue as compiling it takes several minutes.

# check xcode, should yield : /Library/Developer/CommandLineTools
xcode-select -p

# check xcode, should yield : xcode-select version 2384
xcode-select -v

# install xcode-select
xcode-select --install

# reinstall openssl and version 3
brew reinstall [email protected]

# install build dependancies
brew install openssl readline libyaml zlib bison [email protected]

# ensure build is using bison
export PATH="$(brew --prefix [email protected])/bin:$PATH"

# set ruby compilation flags
export CFLAGS="-Wno-error=implicit-function-declaration"
export RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix [email protected]) --with-readline-dir=$(brew --prefix readline) --with-libyaml-dir=$(brew --prefix libyaml) --with-zlib-dir=$(brew --prefix zlib)"

# install ruby via ruby-install
ruby-install ruby 2.6.8

a couple more steps if it fails

# ensure that openssl is linked
brew unlink openssl && brew link openssl --force

# load openssl 1.1 for compilation
export LDFLAGS="-L/opt/homebrew/opt/[email protected]/lib"
export CPPFLAGS="-I/opt/homebrew/opt/[email protected]/include"
export PKG_CONFIG_PATH="/opt/homebrew/opt/[email protected]/lib/pkgconfig"

# install ruby via ruby-install
ruby-install ruby 2.7.7

Answer 2

I had the same issue when I ran the following command: ruby-install ruby 2.6.8 -- --with-openssl-dir=$(brew --prefix [email protected]).

I updated bison with brew install [email protected] and ran export PATH="$(brew --prefix [email protected])/bin:$PATH" to fix ripper. Then, re-running the initial ruby command worked!