Failed to build gem native extension when installing OpenSSL - ruby

Question

So I am following this tutorial: https://meta.discourse.org/t/beginners-guide-to-install-discourse-on-macos-for-development/15772 but when I use bundle install it gives me this error:
An error occurred while installing openssl (2.2.0), and Bundler cannot
continue.
Make sure that `gem install openssl -v '2.2.0' --source 'https://rubygems.org/'`
succeeds before bundling.
along with
Installing openssl 2.2.0 with native extensions
Installing cppjieba_rb 0.3.3 with native extensions
Gem::Ext::BuildError: ERROR: Failed to build gem native extension
but why do I get this?
Running gem install openssl -v '2.2.0' --source 'https://rubygems.org/' gives me...
Building native...
ERROR: Error installing openssl:
ERROR: Failed to build gem native extension.
current directory: /Library/Ruby/Gems/2.6.0/gems/openssl-2.2.0/ext/openssl
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/bin/ruby -I /System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/2.6.0 -r ./siteconf20210225-70291-10x2bpm.rb extconf.rb
checking for t_open() in -lnsl... no
checking for socket() in -lsocket... no
checking for openssl/ssl.h... no
*** extconf.rb failed ***
Could not create Makefile due to some reason, probably lack of necessary
libraries and/or headers. Check the mkmf.log file for more details.
Provided configuration options:
--with-opt-dir
--without-opt-dir
--with-opt-include
--without-opt-include=${opt-dir}/include
--with-opt-lib
--without-opt-lib=${opt-dir}/lib
--with-make-prog
--without-make-prog
--srcdir=.
--curdir
--ruby=/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/bin/$(RUBY_BASE_NAME)
--with-openssl-dir
--with-openssl-include
--without-openssl-include=${openssl-dir}/include
--with-openssl-lib
--without-openssl-lib=${openssl-dir}/lib
--with-kerberos-dir
--without-kerberos-dir
--with-kerberos-include
--without-kerberos-include=${kerberos-dir}/include
--with-kerberos-lib
--without-kerberos-lib=${kerberos-dir}/lib
--with-debug
--without-debug
--enable-debug
--disable-debug
--with-nsllib
--without-nsllib
--with-socketlib
--without-socketlib
--with-openssl-config
--without-openssl-config
--with-pkg-config
--without-pkg-config
extconf.rb:99:in `<main>': OpenSSL library could not be found. You might want to use --with-openssl-dir=<dir> option to specify the prefix where OpenSSL is installed. (RuntimeError)
To see why this extension failed to compile,
/Library/Ruby/Gems/2.6.0/extensions/universal-darwin-20/2.6.0/openssl-2.2.0/mkmf.log
Gem files will remain installed in /Library/Ruby/Gems/2.6.0/gems/openssl-2.2.0 for inspection.
Results logged to /Library/Ruby/Gems/2.6.0/extensions/universal-darwin-20/2.6.0/openssl-2.2.0/gem_make.out
Again, why does this happen? Please help!

Answer 1

openssl gem is basically a set of wrappers around openssl library. And bundler cannot find the library in your system during Building native extensions step. Thus the gem fails to install.
This is weird as the script you linked explicitly installs openssl long before bundling gems
log_info "Upgrading and linking OpenSSL ..."
brew install openssl
brew link openssl --force
Check the script's output for errors (and check if it has reached this step at all). You will probably find the reason for missing openssl library there (or simply try to install openssl manually more using the commands above).
After you install the openssl library check its version using command
openssl version -a
If you have a custom openssl library installation it might help to follow the advice from the error message and install openssl gem manually while specifying the path to openssl library