Library not loaded (libcrypto)

Question

After updating ruby and rubyenv packages I'm facing an error. The libcrypto library is not loaded.

When executing the suggested command it seems that it is searching for openssl in ruby /Users/User/.rvm/rubies/ruby-2.4.1. But on my system I use /usr/local/Cellar/ruby/2.6.5.

$ gem pristine executable-hooks --version 1.3.2
Error loading RubyGems plugin "/Users/User/.rvm/gems/ruby-2.4.1@global/gems/gem-wrappers-1.2.7/lib/rubygems_plugin.rb": dlopen(/Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle, 9): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
  Referenced from: /Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle
  Reason: image not found - /Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle (LoadError)
ERROR:  Loading command: pristine (LoadError)
    dlopen(/Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle, 9): Library not loaded: /usr/local/opt/openssl/lib/libssl.1.0.0.dylib
  Referenced from: /Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle
  Reason: image not found - /Users/User/.rvm/rubies/ruby-2.4.1/lib/ruby/2.4.0/x86_64-darwin16/openssl.bundle
ERROR:  While executing gem ... (NoMethodError)
    undefined method `invoke_with_build_args' for nil:NilClass

I used the above command to diagnose another error (maybe this helps):

$ bundle install --system
Ignoring executable-hooks-1.3.2 because its extensions are not built.  Try: gem pristine executable-hooks --version 1.3.2
Ignoring gem-wrappers-1.2.7 because its extensions are not built.  Try: gem pristine gem-wrappers --version 1.2.7
Ignoring unf_ext-0.0.7.4 because its extensions are not built.  Try: gem pristine unf_ext --version 0.0.7.4
/Users/User/.rbenv/versions/2.3.1/lib/ruby/2.3.0/digest.rb:16:in `const_missing': library not found for class Digest::MD5 -- digest/md5 (LoadError)
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/source/rubygems/remote.rb:26:in `cache_slug'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/fetcher/compact_index.rb:107:in `cache_path'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/fetcher/compact_index.rb:83:in `compact_index_client'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:630:in `warn_on_outdated_bundler'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:15:in `ensure in start'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:16:in `start'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/exe/bundle:35:in `block in <top (required)>'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/friendly_errors.rb:121:in `with_friendly_errors'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/exe/bundle:27:in `<top (required)>'
    from /Users/User/.rbenv/versions/2.3.1/bin/bundle:23:in `load'
    from /Users/User/.rbenv/versions/2.3.1/bin/bundle:23:in `<main>'
mdm:ios si$ export PATH="/usr/local/opt/[email protected]/bin:$PATH"
mdm:ios si$ bundle install --system
Ignoring executable-hooks-1.3.2 because its extensions are not built.  Try: gem pristine executable-hooks --version 1.3.2
Ignoring gem-wrappers-1.2.7 because its extensions are not built.  Try: gem pristine gem-wrappers --version 1.2.7
Ignoring unf_ext-0.0.7.4 because its extensions are not built.  Try: gem pristine unf_ext --version 0.0.7.4
/Users/User/.rbenv/versions/2.3.1/lib/ruby/2.3.0/digest.rb:16:in `const_missing': library not found for class Digest::MD5 -- digest/md5 (LoadError)
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/source/rubygems/remote.rb:26:in `cache_slug'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/fetcher/compact_index.rb:107:in `cache_path'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/fetcher/compact_index.rb:83:in `compact_index_client'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:630:in `warn_on_outdated_bundler'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:15:in `ensure in start'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/cli.rb:16:in `start'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/exe/bundle:35:in `block in <top (required)>'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/lib/bundler/friendly_errors.rb:121:in `with_friendly_errors'
    from /Users/User/.rvm/gems/ruby-2.4.1@global/gems/bundler-1.15.1/exe/bundle:27:in `<top (required)>'
    from /Users/User/.rbenv/versions/2.3.1/bin/bundle:23:in `load'
    from /Users/User/.rbenv/versions/2.3.1/bin/bundle:23:in `<main>'

Macrae

What happens if you try what the error message suggested? gem pristine executable-hooks --version 1.3.2? – Overreach

Tried that, seems that I have a linking problem (see updated question). – Macrae

Answer 1

I did a quick test:

rvm 2.6.5

To determine that ruby-2.6.5 was not installed, so I installed it:

rvm install "ruby-2.6.5"

Macrae

Ok. Good. This should work also if you wish to stick with RVM. Remember to set the new Ruby as default after you install. – Overreach

Answer 2

You say you are using the system Ruby from /usr/local/ yet the error messages are from an RVM installation.

You need to either uninstall RVM, or set the system Ruby as default for RVM:

rvm --default use system

More discussion here:
Disable RVM or use Ruby which was installed without RVM?

Overreach