After OSX 10.10.4 update(?): Unable to install 2.2.0 or 2.2.1, run gem install bundler with 2.2.2 - missing zlib

[davidcpell]

I've been having the following issues with rbenv since a recent uninstall/reinstall of rbenv and ruby-build (around the same time as updating to OSX 10.10.4 and Command Line Tools 6.4). I was uninstalling/reinstalling in hopes that it would fix an unrelated problem. However, I now can't build 2.2.0 or 2.2.1. I can build 2.2.2 but am unable to use gem install bundler due to a supposedly missing zlib package. I have run brew update, brew doctor, etc before installing rbenv and ruby-build.

MacBook-Pro:app me$ which ruby
/Users/me/.rbenv/shims/ruby
MacBook-Pro:app me$ rbenv versions
  system
* 2.2.2 (set by /Users/me/work/app/.ruby-version)
MacBook-Pro:app me$ gem install bundler
ERROR:  Loading command: install (LoadError)
    cannot load such file -- zlib
ERROR:  While executing gem ... (NoMethodError)
    undefined method `invoke_with_build_args' for nil:NilClass

MacBook-Pro:~ me$ rbenv install 2.2.0
Downloading ruby-2.2.0.tar.gz...
-> http://dqw8nmjcqpjn7.cloudfront.net/7671e394abfb5d262fbcd3b27a71bf78737c7e9347fa21c39e58b0bb9c4840fc
Installing ruby-2.2.0...

BUILD FAILED (OS X 10.10.4 using ruby-build 20150519)

Inspect or clean up the working tree at /var/folders/rm/38vbv5g952s54r1txrmrdlf40000gn/T/ruby-build.20150705212307.49958
Results logged to /var/folders/rm/38vbv5g952s54r1txrmrdlf40000gn/T/ruby-build.20150705212307.49958.log

Last 10 log lines:
    from /private/var/folders/rm/38vbv5g952s54r1txrmrdlf40000gn/T/ruby-build.20150705212307.49958/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
    from /private/var/folders/rm/38vbv5g952s54r1txrmrdlf40000gn/T/ruby-build.20150705212307.49958/ruby-2.2.0/lib/rubygems.rb:556:in `install'
    from ./tool/rbinstall.rb:717:in `block (2 levels) in <main>'
    from ./tool/rbinstall.rb:716:in `each'
    from ./tool/rbinstall.rb:716:in `block in <main>'
    from ./tool/rbinstall.rb:749:in `call'
    from ./tool/rbinstall.rb:749:in `block in <main>'
    from ./tool/rbinstall.rb:746:in `each'
    from ./tool/rbinstall.rb:746:in `<main>'
make: *** [do-install-all] Error 1 

When I open up the error log and find the point of failure, it's the same as the above bundler problem with 2.2.2:

installing default gems:      /Users/me/.rbenv/versions/2.2.0/lib/ruby/gems/2.2.0 (build_info, cache, doc, extensions, gems, specifications)
                              bigdecimal 1.2.6
                              io-console 0.4.3
                              json 1.8.1
                              psych 2.0.8
                              rake 10.4.2
                              rdoc 4.2.0
installing bundle gems:       /Users/me/.rbenv/versions/2.2.0/lib/ruby/gems/2.2.0 (build_info, cache, doc, extensions, gems, specifications)
/private/var/folders/rm/38vbv5g952s54r1txrmrdlf40000gn/T/ruby-build.20150705212307.49958/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require': cannot load such file -- zlib (LoadError)

I have seen similar problems with cannot load such file -- zlib (it's even mentioned in the wiki) but that normally seems to be a problem with Linux systems rather than OSX.

I'm at the end of what I know to do to try to debug this and I thought I would mention/report it here.

OSX 10.10.4
Command Line Tools 6.4
rbenv 0.4.0
ruby-build 20150519

[davidcpell]

well...it looks like zlib must be in Xcode proper and not Command Line Tools...and either something happened to my Xcode installation or I needed to update it manually after the OSX 10.10.4 upgrade. I checked the App Store and noticed I was able to update it and, after I did, the problem went away. I'll go ahead and close this!

[eexit]

Hello,

Sorry to reopen this topic but I have the same problem on Catalina. My installation is fresh, I even reinstalled XCode and no matter what I'm trying, it won't install Ruby 2.2.0:

brew install zlib rbenv ruby-build
brew install rbenv/tap/openssl@1.0
RUBY_CONFIGURE_OPTS="--with-openssl-dir=$(brew --prefix openssl@1.0)" rbenv install 2.2.0
Downloading ruby-2.2.0.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.2/ruby-2.2.0.tar.bz2
Installing ruby-2.2.0...

WARNING: ruby-2.2.0 is past its end of life and is now unsupported.
It no longer receives bug fixes or critical security updates.

ruby-build: using readline from homebrew

BUILD FAILED (Mac OS X 10.15.6 using ruby-build 20200819)

Inspect or clean up the working tree at /var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD
Results logged to /var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.log

Last 10 log lines:
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems.rb:556:in `install'
	from ./tool/rbinstall.rb:717:in `block (2 levels) in <main>'
	from ./tool/rbinstall.rb:716:in `each'
	from ./tool/rbinstall.rb:716:in `block in <main>'
	from ./tool/rbinstall.rb:749:in `call'
	from ./tool/rbinstall.rb:749:in `block in <main>'
	from ./tool/rbinstall.rb:746:in `each'
	from ./tool/rbinstall.rb:746:in `<main>'
make: *** [do-install-all] Error 1
zsh: exit 1

In the logs, near the end:

config.status: creating x86_64-darwin19-fake.rb
./miniruby -I./lib -I. -I.ext/common  ./tool/runruby.rb --extout=.ext  -- --disable-gems -r./x86_64-darwin19-fake ./tool/rbinstall.rb --make="make" --dest-dir="" --extout=".ext" --mflags="" --make-flags="" --data-mode=0644 --prog-mode=0755 --installed-list .installed.list --mantype="doc" --install=all --rdoc-output=".ext/rdoc"
installing binary commands:   /Users/jberthelot/.rbenv/versions/2.2.0/bin
installing base libraries:    /Users/jberthelot/.rbenv/versions/2.2.0/lib
installing arch files:        /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/2.2.0/x86_64-darwin19
installing pkgconfig data:    /Users/jberthelot/.rbenv/versions/2.2.0/lib/pkgconfig
installing command scripts:   /Users/jberthelot/.rbenv/versions/2.2.0/bin
installing library scripts:   /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/2.2.0
installing common headers:    /Users/jberthelot/.rbenv/versions/2.2.0/include/ruby-2.2.0
installing manpages:          /Users/jberthelot/.rbenv/versions/2.2.0/share/man/man1
installing extension objects: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/2.2.0/x86_64-darwin19
installing extension objects: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/site_ruby/2.2.0/x86_64-darwin19
installing extension objects: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/vendor_ruby/2.2.0/x86_64-darwin19
installing extension headers: /Users/jberthelot/.rbenv/versions/2.2.0/include/ruby-2.2.0/x86_64-darwin19
installing extension scripts: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/2.2.0
installing extension scripts: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/site_ruby/2.2.0
installing extension scripts: /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/vendor_ruby/2.2.0
installing extension headers: /Users/jberthelot/.rbenv/versions/2.2.0/include/ruby-2.2.0/ruby
installing default gems:      /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/gems/2.2.0 (build_info, cache, doc, extensions, gems, specifications)
                              bigdecimal 1.2.6
                              io-console 0.4.3
                              json 1.8.1
                              psych 2.0.8
                              rake 10.4.2
                              rdoc 4.2.0
installing bundle gems:       /Users/jberthelot/.rbenv/versions/2.2.0/lib/ruby/gems/2.2.0 (build_info, cache, doc, extensions, gems, specifications)
/private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require': cannot load such file -- zlib (LoadError)
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/package.rb:46:in `<top (required)>'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/dependency_installer.rb:3:in `<top (required)>'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems/core_ext/kernel_require.rb:54:in `require'
	from /private/var/folders/zr/xscq74t95293jr3k2dj75pyw0000gn/T/ruby-build.20200917111734.72324.wL7hCD/ruby-2.2.0/lib/rubygems.rb:556:in `install'
	from ./tool/rbinstall.rb:717:in `block (2 levels) in <main>'
	from ./tool/rbinstall.rb:716:in `each'
	from ./tool/rbinstall.rb:716:in `block in <main>'
	from ./tool/rbinstall.rb:749:in `call'
	from ./tool/rbinstall.rb:749:in `block in <main>'
	from ./tool/rbinstall.rb:746:in `each'
	from ./tool/rbinstall.rb:746:in `<main>'
make: *** [do-install-all] Error 1

It seems that Ruby is compiling just fine but gem is failing.

Rbenv-doctor output:

curl -fsSL https://github.com/rbenv/rbenv-installer/raw/master/bin/rbenv-doctor | bash

Checking for `rbenv' in PATH: /usr/local/bin/rbenv
Checking for rbenv shims in PATH: OK
Checking `rbenv install' support: /usr/local/bin/rbenv-install (ruby-build 20200819)
Counting installed Ruby versions: none
  There aren't any Ruby versions installed under `/Users/jberthelot/.rbenv/versions'.
  You can install Ruby versions like so: rbenv install 2.2.4
Checking RubyGems settings: OK
Auditing installed plugins: OK

ll /usr/lib/libz*
lrwxr-xr-x 1 root wheel   12 Aug 28 15:54 /usr/lib/libz.1.1.3.dylib -> libz.1.dylib
lrwxr-xr-x 1 root wheel   12 Aug 28 15:54 /usr/lib/libz.1.2.11.dylib -> libz.1.dylib
lrwxr-xr-x 1 root wheel   12 Aug 28 15:54 /usr/lib/libz.1.2.5.dylib -> libz.1.dylib
lrwxr-xr-x 1 root wheel   12 Aug 28 15:54 /usr/lib/libz.1.2.8.dylib -> libz.1.dylib
-rwxr-xr-x 1 root wheel 104K Aug 10 20:39 /usr/lib/libz.1.dylib
lrwxr-xr-x 1 root wheel   12 Aug 28 15:54 /usr/lib/libz.dylib -> libz.1.dylib

Any help would be greatly appreciated.
Thanks!